Bobby and Laura are sailing around the world with two full size labradoodles and document their adventures as they go! In the podcast series they will get more in depth on topics related to cruising in general and cruising with pets. Some of the information will be regionally specific and some will be a broader base. Come follow along with us and enjoy the ride!
For most of human history, people who felt trapped by their circumstances could leave everything behind and head toward a new frontier. They could escape their social class, family reputation, past failures, or limited opportunities and try to build something entirely new.But do those kinds of fresh starts still exist?In this episode, I explore why starting over may be harder today than it was for previous generations, why fewer people are willing to risk everything, and whether the world has simply run out of places where your past does not define your future.I also share a story from my own family history about an ancestor who, according to the story passed down through my family, was the thirteenth son of an English lord. With little chance of inheriting anything, he left England for the New World to build a life of his own.We discuss the influence of the frontier on American ambition and entrepreneurship, the uncomfortable truth that these lands were never actually empty, and whether technology, space, artificial intelligence, international living, and online businesses have become the new frontiers.Maybe there are no truly undiscovered places left. But perhaps the biggest frontier has always been the decision to walk away from the life you were given and attempt to create a different one.Download the Sailing Doodles Crew App on iOS and come join the Crew!https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361or join our Patreonhttp://www.patreon.com/sailingdoodlesor become a channel memberhttps://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/joinDonate Via Paypal to helphttp://www.paypal.me/sailingdoodlesOur partners:Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/Precision Sails:https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodlesHighfield Boats:https://www.highfieldboats.com/#Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
In this Ask Me Anything podcast, I answer some of the questions patrons and viewers have been asking most.I start with Nika—whether she’ll be joining me again, how we got along, and what might be next. I also share the scariest experience I’ve ever had at sea: the night my old boat nearly caught fire and sank near Cape Hatteras. I included clips from the original video and explain what happened from my perspective.I also give an update on my health, future cruising plans, the Great Loop, the Great Lakes, Maverick, and several other questions submitted by viewers.There are a few major questions about Maverick and my discussions with Island Spirit that I’m not ready to answer publicly yet. I did answer them fully in the uncut patron version of this podcast.Become a patron to watch the complete, unedited episode and hear the parts that were removed from the public version.The full 40-minute documentary about the Cape Hatteras incident is also available as a pay-per-view video on my website.Watch the Scary moment my boat almost caught fire and sunk:https://sailingdoodles.com/fire-at-sea/Download the Sailing Doodles Crew App on iOS and come join the Crew!https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361or join our Patreonhttp://www.patreon.com/sailingdoodlesor become a channel memberhttps://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/joinDonate Via Paypal to helphttp://www.paypal.me/sailingdoodlesOur partners:Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/Precision Sails:https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodlesHighfield Boats:https://www.highfieldboats.com/#Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
Owning a brand-new hybrid-electric yacht has been exciting—but it has also come with a much steeper learning curve than expected.In this podcast, I give an honest update on my first few weeks aboard the Island Spirit 525e. I walk through the technical issues we’ve experienced so far, including repeated generator faults, problems within the drive-battery system, charging limitations, and some of the other complications that have interrupted our cruising through Thailand.I explain what happened, what the technicians and builder have done to investigate the problems, and why the generator and battery systems are so important on a yacht designed around electric propulsion.This isn’t meant to attack anyone or declare the entire concept a failure. New boats often have issues, and this yacht uses relatively new and complex technology. I simply want to be transparent with the audience about the good, the bad, and the decisions still ahead.Do we continue improving the hybrid system, make major changes, or consider a more conventional setup? At this point, I’m keeping an open mind.Download the Sailing Doodles Crew App on iOS and come join the Crew!https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361or join our Patreonhttp://www.patreon.com/sailingdoodlesor become a channel memberhttps://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/joinDonate Via Paypal to helphttp://www.paypal.me/sailingdoodlesOur partners:Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/Precision Sails:https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodlesHighfield Boats:https://www.highfieldboats.com/#Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
I’m back with the second half of my patron Q&A, and this time we’re talking about what kind of boat I should buy for my next adventure. Would a diesel Sea Ray-style express cruiser work for Florida, the Keys, the Bahamas, and potentially farther into the Caribbean? Or would I be better off with a trawler, a traditional motor yacht, or something designed for longer-range cruising? I discuss the features, size, speed, dinghy setup, and practical limitations I would consider before buying. I also answer questions about whether I would collaborate with high-performance powerboat channels, meeting up with other content creators while traveling, and how Cougar and Merlin react to the constant stream of new people joining the boat. Thanks to everyone who submitted questions. Let me know what boat you think would make the best next chapter for Sailing Doodles. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
A few weeks ago I shared an idea that I thought could completely change the way people experience luxury sailing. Then I asked for your feedback. Hundreds of comments later—and one incredibly detailed blog from a viewer—I realized I had made some major mistakes. In this episode I explain what I got wrong, why the original model probably wouldn't work, and the new direction I'm considering. We dive into whole-boat memberships vs. cabin memberships, pricing, charter economics, premium weeks, refundable deposits, and how this idea might actually become a real business. I still don't know if this will ever happen, but it's already a much better idea because of your feedback. As always, I'd love to hear what you think. Would you join something like this? What would you change? Here is Sam's Blog post: https://sveoti.net/an-open-letter-to-bob-white-sailing-doodles-buying-a-yacht-for-you/ Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
In this patron Q&A podcast, I answer some of the most common—and most interesting—questions viewers have been asking. I talk about what happened with recent crew members, how I find people to join the boat, the couple who were supposed to launch a Sailing Doodles spin-off channel, whether I’m in a relationship, my changing thoughts about Thailand, plans for the new catamaran, the Mediterranean, the flotilla, and whether I’m seriously considering buying a motor yacht and doing the Great Loop. I also tell a disturbing offshore story about a friend who hired a delivery captain to sail his yacht from the Mediterranean to the Caribbean. In the middle of the Atlantic, the captain suffered a serious mental-health crisis and threatened to jump overboard. My friend had to change course and divert the yacht to the Azores so the captain could safely get ashore and receive help. It raises an important question: what do you do when someone panics, becomes unstable, or simply cannot handle being at sea—with nowhere nearby to get off the boat? Thanks to all the patrons and viewers who submitted questions. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
What if there was a better way to own a luxury yacht? I've been working on a business idea that I honestly can't decide is brilliant... or completely crazy. Imagine having access to a $1.4 million sailing catamaran that cruises the Mediterranean, Caribbean, Thailand and beyond, without having to buy the whole boat yourself. In this episode I walk through the concept, the numbers, the challenges, and the biggest objections I've already heard. Most importantly, I want YOUR feedback. Would you join something like this? What would make you say yes... and what would make you run away? Leave your thoughts in the comments. Your feedback may completely change this idea. Fill out the survey if you want to go in on this with me! https://docs.google.com/forms/d/e/1FAIpQLSf5cP4pI-etL7w761rhN6DqTA81sLEbRsI0KTpkF3Jhf31-kg/viewform?usp=dialog Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodle
In this episode, I talk through a big realization about the future of Sailing Doodles: because of location, weather, and cruising seasons, I may only be able to film on my new catamaran about four months a year. That creates a real problem. If I want to keep making consistent boat content, I may need a second boat. So I’m thinking about buying a smaller motor yacht to keep in Florida and use for cruising the Bahamas, and maybe even doing parts of the Great Loop. I go through the different types of boats I’m considering, what makes sense for the channel, what fits the budget, diesel vs gas, speed vs efficiency, and whether a motor yacht could be the right move for the next chapter. Is this a smart backup plan, or am I just trying to talk myself into buying another boat?
Most people have a dream. Maybe it’s sailing around the world, building a cabin in the mountains, starting a farm, opening a business, moving overseas, or just walking away from a life that looks successful on paper but doesn’t actually make you happy. But most people never do it. Not because the dream is impossible, but because they keep waiting until they’re ready. In this episode, I talk about why I believe you have to set a date, prepare as best you can, and then go. My dream was sailing around the world on a yacht, but this isn’t just about sailing. It’s about risk, freedom, time, work, and the trap of waiting for the perfect moment. I also talk about leaving a good career, the idea of “no risk, no reward,” why doing nothing is also a risk, and why chasing the dream might not work out exactly how you planned — but that doesn’t mean it wasn’t worth doing. You can always get another job. You can’t always get another life. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
In this episode, I’m answering your questions from Patreon, YouTube members, and the Sailing Doodles app. We start with the big one: my recent health scare, the blood clots and thrombosis, whether it could be connected to my past stroke, how medical care has been overseas, and what recovery might look like from here. Then we get into the questions everyone always wants answered: What’s going on with Olivia? Is she coming back to the boat? What happened with the Brazilian girl? Will Chloe or Sailing Miss Lone Star return? I also talk about the dogs, the future of the new Island Spirit 525e, what the delivery crew thought of the boat, the electrical and solar questions, the damaged old hull, possible cruising plans, the Med, the Pacific, RV travel, Burning Man, and what’s next for Sailing Doodles. Thanks for all the questions, support, and well wishes. It has been a strange and stressful chapter, but I’m doing my best to stay positive and figure out the path forward. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
After a big health scare, I’ve had to ask myself some hard questions about the future of Sailing Doodles. I just bought my dream yacht, but now I’m dealing with blood clots and thrombosis in major abdominal veins, and I still don’t have all the answers about what caused it or what the long-term prognosis looks like. For a while, there was even concern it could be cancer, which thankfully seems to have been ruled out. In this episode, I talk honestly about what this could mean for my future: whether I can keep sailing long term, what happens to the new yacht if my health changes, whether I’d sell the boat, hire crew, slow down, or pivot the channel completely. I also talk about what retirement might actually look like, whether I regret buying the boat right before this happened, and what happens to the dogs, the crew, the travel plans, and Sailing Doodles as a whole. This one is personal. I don’t have all the answers yet, but this scare has definitely changed how I think about life, health, travel, and the future of the channel. Thanks for watching and for all the support. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
In this episode, I talk about the medical issue that suddenly interrupted my life and my plans for Sailing Doodles. It started with abdominal pain that I thought might be something minor, but after hospital visits, scans, and more tests, doctors found inflammation around my pancreas and blood clots in the portal vein. For a short time, there was a real fear that it could be pancreatic cancer, which was obviously terrifying. Right now, I’m still waiting on a proper diagnosis. It could be something autoimmune, it could be related to pancreatitis, or it could be something else entirely. I’m on blood thinners, getting more testing done, and trying to understand what this means for my future. I also talk about what this could mean for Sailing Doodles, cruising plans, the new boat, and how something like this makes you rethink everything pretty quickly. This is a more personal episode, but I wanted to be honest about where things stand and what I’m dealing with. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
After years of delays, setbacks, and finally taking delivery of my new Island Spirit 525e… I’ve run into another problem. Because of Thailand’s import and customs rules, I now have to sail the boat roughly 72 hours to Malaysia, clear customs, and then sail all the way back to Thailand just so the yacht can legally return as a tourist vessel. It’s expensive, time consuming, exhausting… and honestly pretty frustrating after everything it took to finally get this boat in the water. In this episode of the Sailing Doodles Podcast, I break down: Why I have to leave Thailand The confusing customs/import situation My planned route to Malaysia The risks of an offshore passage this soon Costs, timing, and logistics What this means for the future of the boat Owning a yacht overseas definitely isn’t always as glamorous as it looks online. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles
After years of planning, delays, factory visits, and a whole lot of frustration, my new Island Spirit 525e electric catamaran is finally in the water — and sailing. In this episode, I talk through the last few crazy weeks of the build: inspecting the boat at the factory, the Buddhist blessing ceremony, the nerve-racking truck move to the marina, launching the yacht, and finally taking her out for the first sail and sea trial. I’ll share what went right, what still needs work, what surprised me most about the boat’s performance, and whether this electric catamaran project is turning out the way I hoped. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/
Electric boats are no longer some far-off future idea — they’re here, and my new Island Spirit 525e is a perfect example. With a 210 kWh battery bank, two 65 kW electric motors, and around 80 nautical miles of electric range at 6 knots, this is a serious electric propulsion system. In this episode, I talk about the safety side of modern electric boats: lithium batteries, battery monitoring, cooling systems, electric propulsion, installation quality, and why today’s systems are much safer than they were just a few years ago. I also get into one of the biggest fears on any modern sailboat: lightning. A lightning strike can cause massive damage, destroy electronics, and create electrical gremlins that last for years. That’s why I installed the CMCE Sertec lightning prevention system on my boat. I explain how it works, why I think lightning protection is essential on a modern electric catamaran, and why protecting all these electronics and batteries matters more than ever. We’ll also talk about maintenance, reliability, generator backup, energy management, and what life is really like with a modern lithium and electric propulsion system onboard. Topics in this episode: Lithium battery safety on boats Electric propulsion systems Battery monitoring and cooling Lightning protection CMCE Sertec system Generator backup Marine electronics Electric sailing catamarans Island Spirit 525e Modern boat reliability Big takeaway: electric boats are not scary when they’re done right — what’s scary is powerful technology installed casually. And f you are looking for the Sertec lightning prevention system in Asia contact Electrical Marine https://electrical-marine.com/ Otherwise, check out their website: https://marine.sertec.com.py/en/ Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Dating while sailing around tropical islands sounds like it should be easy… but the reality is a lot more complicated. When you live on a boat and cruise full-time, you are constantly moving from one place to the next. You are rarely in one place long enough to casually date, and most cruising destinations are full of couples, families, honeymooners, and retired cruisers — not single people looking to date. Then add YouTube into the mix. In this episode, I talk about what it is really like trying to date while living on a boat, traveling internationally, filming my life for YouTube, and dealing with the audience speculation that comes with every new woman who appears on the channel. We talk about dating apps, meeting people in cruising destinations, why relationships can move so fast on a boat, the difference between crew and dating, privacy, jealousy, and how hard it can be to know whether someone is interested in you, the travel, the lifestyle, or the camera. Dating in paradise is not always what people think. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361
The Bahamas pushed cruising fees too far in 2025, and the boating industry says the fallout was immediate: fewer boats, weaker marina occupancy, and millions in lost economic activity across the islands. As of April 1, 2026, they’ve changed the system again. I’m breaking down the new official fee structure, comparing it to the old one, and showing what it means for a typical cruising boat heading to the Bahamas today.
In this episode of the Sailing Doodles Podcast, I finally sit down with Chloe for a real conversation about her background, where she came from, and how she ended up joining the crew. It’s a fun, honest episode where you really get to know her beyond what you see in the videos… But we also share some important news. Chloe will be leaving Sailing Doodles for now to head home and take care of some medical things. We talk about what’s going on, what this means moving forward, and what’s next. It’s not goodbye forever — just a new chapter. Chekc out her Patreon https://www.patreon.com/chloer
In this episode of the Sailing Doodles Podcast, I’m answering your questions—from the new 525e catamaran build to future sailing plans, life in Thailand, and yes… Chloe. We cover everything from boat systems and upgrades, to where I’m sailing next, to how all of this actually works behind the scenes. Nothing is off limits in this one. Topics include: Status of the new Island Spirit 525e Future sailing plans (Maldives, Australia, beyond) Life and relationships on the road and at sea Boat systems, maintenance, and lessons learned Content, Patreon, YouTube, and how it all works Thanks to everyone who submitted questions—these AMA episodes are some of my favorites to do.
For years I assumed I had another 5–10 years as a content creator before technology really started disrupting things. After seeing how fast AI video is advancing… I’m not so sure anymore. AI can now generate voices, scripts, music, and even realistic video scenes. I recently watched several AI-generated reels and videos that honestly fooled me at first. And the scary part is this technology is improving incredibly fast. In this episode I talk about: • AI-generated videos that fooled me • How fast AI video is improving • Why creators might actually lose this battle • How AI could flood YouTube with unlimited content • Whether real creators will still be able to make a living Even if people prefer real creators, the amount of AI content coming could make it almost impossible to compete. But there may still be one thing AI can’t replicate… real life experiences. So is this the end of creators, or just the next evolution of content creation?
Ever wondered how hard it is to move pets internationally? visit AE Pets https://www.aepetsgo.com In this episode of The Sailing Doodles Podcast, I break down exactly what it took to move my two dogs from the United States all the way to Thailand. There are a lot more steps involved than most people realize — health certificates, government approvals, airline regulations, quarantine rules, and more. To help explain the process, I sit down with James from AE Pets International, the company that handled the logistics of transporting my dogs. We talk about how international pet shipping works, what pet owners need to know before moving abroad, and how professionals coordinate everything from paperwork to flights to make sure pets arrive safely. If you’re planning to travel or relocate overseas with your pets, this episode will give you a behind-the-scenes look at the process and how to make it much easier. Topics we cover: • The paperwork required to ship pets internationally • Health certificates and vaccination requirements • Airline cargo vs passenger transport • What happens when pets land in a new country • Common mistakes pet owners make • How pet shipping companies simplify the process Whether you're moving abroad, sailing around the world, or just curious about how pets travel internationally, this episode will walk you through everything. become a patron! https://www.patreon.com/sailingdoodles
In this episode of The Sailing Doodles Podcast, I dive into one of the biggest decisions I’ve ever made… going all-electric with the new catamaran. Why did I choose an electric propulsion system? How does it compare to boats like Fountaine Pajot’s electric cats? What are the real risks — lightning, reliability, long-term maintenance? And what spares and tools will I be carrying to prepare for worst-case scenarios? Then we pivot into your most asked personal questions… – Will there be rotating crew in Thailand? – What’s happening with Flying Doodles and Emma? – Can I get my pilot’s license back? – Does Chloe ever get tired of keeping her real name private? – And yes… how dating works when you’re constantly moving. We also talk YouTube growth “experts,” long-term life plans, the Bronco, and my favorite episode I’ve ever created. Big changes ahead. Let’s get into it.
In this episode of The Sailing Doodles Podcast, I sit down with Emma — the host of Flying Doodles — to talk about her aviation journey, career path, and what really goes on behind the scenes of the channel. From her flight training and early experiences in the cockpit to where she sees her aviation career heading next, Emma shares stories you haven’t heard before. We also talk about the future of Flying Doodles, upcoming projects, and what excites her most about aviation right now. If you’ve been watching Flying Doodles and wondering who Emma really is and how she got here — this is the episode for you. Make sure you check out @flyingdoodles here: https://www.youtube.com/c/FlyingDoodles/ Let us know in the comments: What should we film next on Flying Doodles? #FlyingDoodles #AviationPodcast #PilotLife #SailingDoodles
In this Ask Me Anything episode, I answer the question everyone keeps asking… Who is actually coming with me to Thailand to pick up the new boat? There’s been a lot of speculation about crew, plans, and what’s happening next — so I finally address it. I also talk about: Whether Chloe is joining me Lauryn? Thailand flotilla details What I actually have planned once I get there The current status of the boat raffle RV updates and the Camping World situation Craziest sailing mistakes I’ve ever seen And how to get hired on a sailboat Big year ahead. New boat. New adventures. Possibly new crew. Let’s get into it.
This one feels surreal to say out loud — the new boat is getting very close to completion. In this update, I share where the build is at, what’s left to finish, and why this moment feels different than anything before. After months (and years) of planning, I’ll be flying to Thailand next month to finally step onboard and start the next chapter. I know a lot of you have been following this journey from the beginning, and I can honestly say… I’m just as excited (and nervous) as you are. Thanks for sticking with me — things are about to get really interesting. Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Sailing YouTube looks easier than ever — bigger audiences, better cameras, more success stories. But the reality? It’s harder now than when I started, and most sailing channels don’t even make it past year two. In this episode, I break down why channels really fail — not because they can’t sail, but because they run out of money, burn out, struggle with people, or misunderstand how YouTube actually works today. I talk honestly about how long it took me to break even, living on beans and rice, dealing with burnout that never really goes away, why subscribers matter less than they used to, and why AI might be the biggest challenge creators face next. This isn’t meant to discourage anyone — it’s meant to prepare you. If you’re thinking about starting a sailing channel, or you’ve wondered why so many disappear, this episode is for you.
In this podcast, I answer one of the biggest questions I’ve been getting lately: who’s coming with me to Thailand on the new boat? We talk about the new boat timeline, potential crew lineup, and what this next chapter of Sailing Doodles is really going to look—both on and off camera. I also address questions about Chloe, future appearances, and how I handle bringing new people into the videos while balancing privacy, reality, and the internet’s opinions. We also dive into: Who may be joining the boat in February How crew decisions actually get made Viewer questions about drones, sailing, and life on the water What changes (and what stays the same) with the new boat Big changes ahead—this episode gives you the real story.
A month or so ago, I shared a podcast about the nightmare I was dealing with on my RV — and at the time, I hadn’t even gotten to the worst part yet: needing a full engine overhaul. In this episode, I give a full update on everything that happened afterward, how the situation evolved, and how Camping World ultimately stepped up and made things right. It was a long, stressful process, but in the end they took care of the problem, made me whole, and even got me into a newer and better RV. I believe in being fair and transparent — good or bad — and this episode is about how things actually turned out and why I’m satisfied with the resolution. If you’re an RV owner, considering buying one, or just curious how these situations really get handled behind the scenes, this update is worth listening to.
In this episode, I share my personal thoughts on the tragic aviation accident involving Greg Biffle and his family. I had the opportunity to meet Greg and his wife Kristina about a year and a half ago at Spanish Cay Yacht Club, and they were incredibly kind, welcoming people. This is not an episode about speculation or assigning blame, but rather about acknowledging the human loss, explaining what is currently known, and offering perspective on how unforgiving aviation emergencies can be—especially shortly after takeoff and in marginal weather conditions. Investigations by the Federal Aviation Administration and the National Transportation Safety Board are ongoing, and it will be many months before definitive answers are available. My thoughts and condolences are with everyone affected by this heartbreaking tragedy.
You asked some tough questions, so it’s time to answer them. In this Q&A episode I cover everything from crew changes and relationships, to insurance and the new boat, along with sailing myths, health insurance while cruising, provisioning mistakes, and what’s coming next for Sailing Doodles and the spin-off channel. Nothing scripted, nothing off limits, just honest answers to the questions you’ve been sending in. Thanks to all the patrons and supporters who keep this channel going and help shape these conversations. Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Ever wondered what sailing is really like? After years living aboard, crossing oceans, rescuing boats, breaking boats, and teaching new crews how to sail, I’ve heard every sailing myth in the book… and today we’re busting the big ones. In this episode, we break down the 12 most common (and most misleading!) sailing myths that stop people from getting on the water — including the truth about boat costs, storms, sharks, catamaran safety, anchoring, YouTube crew life, and whether you actually need experience before buying a boat. Whether you’re dreaming of cruising, already sailing, or just love the lifestyle, this podcast will give you a real-world look at what sailing is actually like… the good, the bad, and the hilarious. To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
After many delays, stress, paperwork, and uncertainty… the insurance saga is finally over. As most of you know, the delivery crew had a major mechanical failure last year that led to my boat being totaled. Since then, I’ve been working through the long insurance process behind the scenes. I can’t share specific numbers, terms, or private details because of my NDA — but I can walk you through what the experience was like, what I learned, and how this affects the future of Sailing Doodles. In this episode I cover: What I can legally say about the resolution What this means for the new boat build And what’s next for the channel Thank you to everyone who supported me during this ordeal — the comments, messages, and patience meant more than you know. Time to move forward and get back to sailing! To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Ever wonder where everyday expressions like “three sheets to the wind,” “overboard,” “the bitter end,” or even “windfall” actually came from?
Turns out, tons of common words in English were invented by sailors, pirates, and old-school sea captains, and today we still use them without even thinking about it.
In this episode of the Sailing Doodles Podcast, I break down over 80 everyday words and sayings that all started on ships — from naval terms, pirate slang, emergency commands, rigging language, and old maritime traditions. Some of these are obvious… but most of them will absolutely blow your mind!
If you enjoy sailing, history, language, or just fun trivia, this is a super entertaining deep dive into how much of modern English came from life at sea.
Fair winds and following seas — and thanks for listening!
If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
What upgrades are actually worth the money on an older sailboat… and which ones you should avoid?
In this episode of The Sailing Doodles Podcast, I break down the most valuable upgrades I’ve done across all the boats I’ve owned — from my classic CT-56 to the newer catamarans and charter boats we’ve sailed.
I cover which improvements truly make your boat safer, easier to sail, and more enjoyable… and which “fancy” upgrades usually end up being a waste of money. If you’re shopping for an older cruising boat or planning a refit, this episode will save you thousands.
Topics Covered
Why buying a boat already upgraded is often cheaper
Rigging, sails, and critical safety upgrades
Ground tackle & anchoring systems worth investing in
Autopilots, instruments & navigation upgrades
Electrical systems, lithium, solar & charging
Refrigeration: why it’s usually a later priority
Comfort upgrades: electric winches, watermakers & more
What to skip… and what will absolutely transform your cruising
About the Channel
I’m Bobby from Sailing Doodles. I sail, travel, and document the adventure while running my YouTube channels from around the world — from the Caribbean and the Bahamas to the Mediterranean and beyond.
If you enjoy the episode, hit subscribe and check out the sailing raffles, flotillas, and behind-the-scenes content!
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
The fans didn’t hold back on this one… In this Q&A episode, I answer YOUR questions about the new catamaran, future sailing plans, past crew, and even a few spicy ones about “hot babes” and babies on board
We talk about:
• Updates on the new Island Spirit 525e catamaran (Hull #5)
• Future cruising plans in Thailand and the Mediterranean
• Crew, relationships, and how the channel has evolved
• Life as a full-time liveaboard and YouTuber
• Gear, filming setups, and how the dogs handle land life
Thanks to everyone who submitted questions — I read as many as I could!
Watch next: [link to related podcast or vlog]
Join the Sailing Doodles community: Patreon / Podia links
Follow along on Instagram: @SailingDoodles
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
I just bought a brand-new RV… and it didn’t even make it off the lot before breaking down. Within minutes, the engine started smoking and I quickly realized the EGR cooler had failed, dumping coolant straight into the exhaust.
In this episode of The Sailing Doodles Podcast, I talk about what happened, how I diagnosed the issue, and what comes next. The dealer says they’ll cover the repair — but we’ll see what really happens.
I’ll share what I’ve learned from years of owning boats, planes, and RVs about mechanical failures, warranty claims, and how to handle breakdowns the smart way.
Topics:
How to spot EGR cooler failure symptoms
What happens when coolant enters the exhaust
Towing and dealer negotiations
Lessons learned when buying new rigs
Listen on YouTube, Spotify, or anywhere you get your podcasts.
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
In this episode, I dive into how sailors and cruisers deal with one of the biggest threats on the ocean — hurricanes.
Fifty years ago, crossing an ocean meant hoping you didn’t run into a storm. There was no internet, no satellite tracking, and little warning. Today, we carry a weather computer in our pocket, with live hurricane data, Starlink connectivity, and routing tools that can literally save lives.
We’ll talk about:
How hurricane forecasting has changed in just a few decades
The role of Starlink and modern weather apps at sea
What the “hurricane box” is — and why insurance won’t cover you inside it
How cruisers migrate north and south each year to stay safe
Where sailors ride out storms (the famous “hurricane holes”)
The truth about insurance loopholes and “named storm” clauses
Real stories, lessons learned, and what it’s like to live with hurricane season as a full-time cruiser
If you’ve ever wondered how modern sailors dodge hurricanes — or how it was done before the digital age — this episode will blow your mind.
Leave a comment: Where do you go during hurricane season?
Subscribe for more real-life sailing stories, tech talk, and behind-the-scenes of the cruising lifestyle.
A Queensland superyacht agent was offered $300,000 for a “simple” job — help two divers enter Australia. Days later, one diver was dead, another had vanished, and 100 kilos of cocaine were floating in Newcastle Harbor.
In this episode, Captain Bobby White of The Sailing Doodles Podcast breaks down the true story of James Blake Blee — how financial desperation led to a deadly smuggling plot, what “parasite smuggling” really is, and why this growing underwater drug tactic is spreading around the world.
All details sourced from court reports, News.com.au, ABC Australia, and VICE News investigations.
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
A U.S.-flagged motor yacht was raided by Bahamian authorities in Bimini after a tip-off — and what they found shocked everyone. Ten people were arrested, including the crew, and officers seized a cache of weapons, ammunition, and cash.
In this episode, Captain Bobby White of Sailing Doodles breaks down the facts, shows footage from the local news, takes a look at the yacht’s charter listing, and shares his honest opinions about carrying weapons onboard and the risks every cruiser faces when crossing borders.
I’m not a lawyer — this is my perspective as a captain who’s checked in at Bimini many times. Always verify local laws before you travel.
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
This week’s Sailing Doodles Podcast gets personal. Viewers submitted hundreds of questions — and of course, the most common one was about Laura.
Are Laura and I getting back together? What really happened behind the scenes at the Annapolis Boat Show? And how does Miss Lone Star fit into all this?
I also answer your questions about the new catamaran, future flotillas, the boat raffle, and what’s next for Sailing Doodles in 2026.
Drop your next questions in the comments for the next Q&A episode!
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
This might be the biggest announcement I’ve ever made. I’m looking for two people — ideally a couple — to come sail with me in Thailand this February for four months.
You don’t need sailing or editing experience. I’ll teach you how to sail, how to film, and how to create a YouTube channel like Sailing Doodles.
The goal? To train the next generation of creators and help them launch their own sailing channel when the journey’s done.
In this episode, I explain what I’m looking for, what the experience will be like, and how to apply.
To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com
Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles
This is your chance to change your life — to learn, explore, and start your own adventure.
At the Annapolis Boat Show, Bobby sits down with Amanda and Maryline from Current Yachts, a new brokerage that’s shaking up the traditional 10% commission model. Instead of sky-high broker fees, they’re offering a flat-fee, transparent system — just $1,500 to list your boat and à-la-carte options for everything else. We dive into why they believe the old system is broken, how they’re making boat buying and selling fairer, and what this means for the future of yacht sales.
If you’ve ever thought about selling your boat — or buying one — you won’t want to miss this conversation.
Check out Current Yachts
https://www.currentyachts.com
This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy
https://sailingdoodles.podia.com/sailing-doodles-course-community
or become a channel member
https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join
or join our Patreon
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help
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Fan-favorite Laura from Sailing Doodles Seasons 2 & 3 is back! She joined me at the Annapolis Boat Show with her two young kids, and things got a little… chaotic.
We catch up on what Laura’s been up to since her sailing days, talk about motherhood, life after the show, and the possibility of getting back on the water.
This one’s totally “wheels off” — her 14-month-old demanded plenty of attention (and snacks), interrupted mid-sentence, and even forced an unexpected break for feeding time. It’s messy, real, and absolutely hilarious.
If you’ve missed Laura’s energy, laughter, and down-to-earth honesty — this episode’s for you!
Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles
Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
What started as one man’s dream to sail the world has grown into one of the most ambitious and inspiring sailing projects on YouTube. In this episode of The Sailing Doodles Podcast, I sit down with Nate and Amy from Expedition Drenched to uncover how it all began — from filming underwater expeditions to building a worldwide nonprofit that protects the oceans.
We talk about:
How Nate left everything behind to chase a life at sea
The early struggles of creating a sailing show with a bigger purpose
What makes Expedition Drenched so different from other sailing channels
How their team balances adventure, filmmaking, and marine conservation
If you love sailing, filmmaking, or stories of people chasing meaning over money — this is a must-watch.
Check out Expedition Drenched on Youtube: https://www.youtube.com/@ExpeditionDrenched
Sailing the Caribbean has always been a dream — but is it getting riskier? Between rising fees in the Bahamas, U.S. drug-interdiction ops near Venezuela, and shifting maritime laws, we dive into whether the Caribbean is still the paradise sailors imagine. In this Q&A episode, I answer fan questions on: Safety in the Caribbean today Rising costs in the Bahamas & alternatives like Cuba and the BVIs Planning & paperwork for international cruising Boat ownership, chartering, and insurance lessons Life aboard with crew, pets, and future sailing plans Drop your thoughts in the comments — would YOU still sail the Caribbean right now? Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles
In this special episode, I’m sharing my full life story — from my childhood sailing a Sunfish on my grandparents’ lake, to my aviation career flying Gulfstreams for celebrities, to the stroke that ended my flying days, and how that ultimately led to creating Sailing Doodles. It’s been a wild ride: flying rockstars around the world, living in Nigeria and Dubai, surviving a medical crisis, and then finally selling everything to chase the dream of sailing full time. I’ll take you through the twists, setbacks, and adventures that brought me here today. If you’ve ever wondered how Sailing Doodles started — this is the story behind it all.
Ever dreamed of selling it all and retiring to sail the world? In this episode of The Sailing Doodles Podcast, Bobby breaks down what it really takes to make that dream happen. From health and fitness (because sailing isn’t a spectator sport), to money and income streams, to choosing the right boat and lifestyle — we cover it all. Whether you’re 55 and planning ahead or 67 and wondering if it’s too late, this episode gives you the honest truth about the realities of retiring at sea. Topics include: Why your health matters more than your bank account How much money you really need to cruise full-time Passive vs. non-passive income while sailing Why your boat should be paid off before you cast off The mental and lifestyle adjustments that make or break retirement cruising Subscribe for more stories, tips, and real talk about life on the water!
t’s time for another viewer Q&A podcast! In this episode, I answer your most popular questions about life on Nauti Dogs, the upcoming new catamaran, what’s happening with the crew, and even some personal stuff you’ve all been curious about. We cover everything from: Plans for raffling off Nauti Dogs Who might join as the first crew on the new boat My thoughts on flotillas, the Great Lakes, and future destinations Tech and maintenance questions — chart plotters, radar, twin-engine sync Personal topics like crew relationships, family, and even those AI “net worth” videos Thanks to everyone who submitted questions on YouTube, Patreon, and Podia — you make these episodes possible! If you want to submit your own questions for future podcasts, join our community here: [link to Patreon/Podia] get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles Make an appointment to see the Island Spirit 525e. Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Think the ocean is lawless? Think again. In this episode we dive into some of the quirkiest maritime laws that still affect sailors today — from the Coast Guard’s power to board your boat anytime without probable cause, to the myth of 33% salvage rewards, to fines for flying the wrong or tattered flag, bizarre anchoring restrictions, and even odd crew contract rules. Topics covered: Coast Guard boarding authority (Revenue Act roots & Prohibition era) Salvage rights & the truth behind the 33% myth Courtesy flag fines & quirky traditions Anchoring bans, seagrass zones, and “pay-to-anchor” politics Crew contracts, Bible laws, and desertion rights Have you ever been boarded, fined, or tangled up in a weird maritime rule? Share your story in the comments — I’d love to hear it. get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles Make an appointment to see the Island Spirit 525e. Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
It’s time for another Q&A podcast with questions straight from our amazing Patrons and YouTube Members! In this episode, I cover: The biggest sailing mistakes I’ve made (and what I learned) Updates on the new catamaran in Thailand and what’s next for Sailing Doodles Thoughts on circumnavigation, the Pacific vs. Caribbean, and charter advice Crew questions — who’s joining, what happened with past crew, and Aubrey’s future plans The latest on insurance, gear, and electric boat tech Plus stories about the dogs, Burning Man, and life on the water Huge thanks to our supporters who submitted these questions — if you’d like to be part of the next Q&A, join us on Patreon or as a YouTube Member. Don’t forget to subscribe for more sailing adventures, podcasts, and behind-the-scenes updates! get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles Make an appointment to see the Island Spirit 525e. Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
In this episode of The Sailing Doodles Podcast, I sit down with Lauryn from Lost Lauryn to talk about her life of adventure. She’s built a following with her motorcycle channel, traveling on two wheels and sharing her journey, and recently she joined me on a sailing trip at sea. We dive into: How she started her motorcycle channel and what inspires her adventures The challenges (and rewards) of documenting life on the road Her experience sailing with me and what surprised her most about life on the water What’s next for her in both motorcycles and sailing It’s a fun conversation about chasing freedom, creating content, and living life off the beaten path. Don’t forget to subscribe for more sailing stories, travel adventures, and conversations with fascinating guests. This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles
In this episode of The Sailing Doodles Podcast, I sit down with fellow YouTuber Auburey from Sailing Miss Lone Star while we’re in Greece chartering a catamaran together. We talk about: Her journey into sailing and YouTube What it’s like sailing with an 11-month-old baby on board Our first time sailing together from Athens to Aegina The ups and downs of life as full-time sailing creators It’s a fun and honest conversation about the realities of sailing, motherhood at sea, and the adventures that come with chasing this lifestyle. Make sure to check out Auburey’s channel Sailing Miss Lone Star and subscribe for more podcasts with sailors, cruisers, and adventurers from around the world. Want to charter a boat in Greece! Check out Istion and get 10% off with out discount code "DOODLES10" Head over to: https://bit.ly/DOODLES10 This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles
In this episode, I take a moment to address some recent negativity from former crewmates. While I won’t name anyone or speak ill of them, I wanted to share my feelings of disappointment and how I’m choosing to respond with positivity. I also want to thank everyone who’s sailed with me over the years, and I’m honored by the memories we’ve shared. On a brighter note, former crewmate Sydney sent in a beautiful video sharing her appreciation for her time on board. Tune in for a mix of gratitude, reflection, and a little behind-the-scenes honesty. Let Sydney whip you into shape! https://future.co/?code=sydney_p&rdrorigin=%2Fsydney_p Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
From lightning strikes and engine failure to fires and man overboard situations—this episode dives deep into the scariest things that can happen on a boat. I’ve lived through a few of these, and others are every sailor’s nightmare. But fear not—this episode isn’t just about horror stories. We break down how often these emergencies happen and give real-world tips on how to prevent or survive each one. If you’ve got a wild sea story, drop it in the comments—I might feature it in a future episode! Watch the full video of my scary moment catching fire around Cape hatteras. https://www.sailingdoodles.com/fire-at-sea/ Check out Electrical Marine in Thailand https://www.electrical-marine.com Protect your boat with SerTec: https://www.sertecmarine.com/en/
In this episode of The Sailing Doodles Podcast, I’m giving you an exclusive first look at Hull #3 of my brand-new catamaran! It’s currently on a ship en route to Annapolis, and I couldn’t be more excited to finally share the journey with you. This is the boat that will take Sailing Doodles to the next level—literally across oceans—and you’re getting the inside scoop before anyone else. Come see it in person! I’ll be at the Annapolis Boat Show, and you’re invited to come check out the new boat for yourself. It’s your chance to step aboard, meet the team, and get a feel for the boat you’ll be seeing a lot of in upcoming videos. Annapolis Boat Show — Be There! Let me know in the comments if you’re coming! Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles
Everyone sees the bikinis, sunsets, and crystal-clear water… but what does it really take to film a successful sailing YouTube channel? In this episode of the Sailing Doodles Podcast, I break down what goes on behind the scenes—from the long hours editing and filming, to the planning, crew management, and sacrifices it takes to stay consistent. I’ll also share why you have to treat this like a full-time job if you want to succeed, how many videos it actually takes to build momentum, and answer some of your most asked questions about gear, crew, burnout, and bloopers. Want to start your own channel? Start here. This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
After years of sailing with dozens of amazing crew members, I finally answer one of the most asked questions — Who was my favorite? From wild adventures to quiet sunsets, I look back on everyone who’s joined me aboard and share my thoughts on what made each of them special. Plus, I answer a bunch more of your fan questions — about relationships, cruising costs, boat life, and what I’d do if I weren’t doing this at all. Chime in down in the comments — who was your favorite crew member to watch? This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
The Bahamas just hiked their cruising permit fees—and boaters are not happy. In this episode of The Sailing Doodles Podcast, we break down the old vs. new fees, what’s changed, and how it's impacting the cruising community. Are these changes smart revenue moves or a huge mistake that could cost the Bahamas its sailing tourism industry? I’ll share the facts, the fallout, and what this means for cruisers of all types. Check out ArunaLight and use code "doodles10" for 10% off! https://www.arunalight.com This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
In this episode of the Sailing Doodles Podcast, I answer the top questions submitted by our fans and patrons. From frustrating insurance delays on the Island Spirit 525 to dating challenges while living full-time on a sailboat — nothing’s off limits. We talk: Insurance delays and the new catamaran timeline What it’s really like choosing crew — and what I look for Dating while sailing The truth about living aboard with dogs Tech talk: hydrogenerators, drones, and boat systems Plus… the biggest waves and sharks I’ve ever seen! If you've ever wondered what goes on behind the scenes of Sailing Doodles, this episode dives deep. Available on YouTube, Spotify, and Apple Podcasts. Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/
Ever wondered how much it really costs to live and cruise on a sailboat? In this episode, Bobby breaks down the actual monthly expenses of full-time boat life—from marina fees and diesel costs to food, maintenance, and those sneaky hidden costs no one warns you about. Whether you're planning to set sail soon or just dreaming of escaping the 9-to-5, this episode gives you a realistic look at the dollars behind the dream. Chapters include: Monthly cruising budget breakdown Unexpected boat expenses Cost-saving tips from years at sea Is cruising really cheaper than land life? This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles
In this episode of the Sailing Doodles Podcast, I sit down with our newest crew member, Jennifer Brown (@jenniferbrownakajb) — a model, actress, and influencer who's traded the runway for the rigging. We talk about her first impressions of life aboard, her background in entertainment, and what it’s like transitioning into the world of sailing. From sunsets to salty decks, Jennifer shares what she’s loving (and learning) about cruising life. Don’t miss this fun conversation about adventure, change, and chasing freedom on the water! This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
In this special Q&A episode of the Sailing Doodles Podcast, I’m answering your best questions from Patreon, Podia, and YouTube Members! From what really happened with former crew like Lauryn and Amanda, to whether my boat is still worth fixing… nothing is off the table. We’re diving into: My relationship with past and current crew Behind-the-scenes costs of Sailing Doodles Insurance battles and boat maintenance headaches Why the Chesapeake? Why not the Med? What I’d do if YouTube disappeared tomorrow The future of Nauti Dogs, Maverick #2, and life onboard Thanks to everyone who submitted thoughtful (and juicy!) questions. If you want yours featured in the next one, join the community on Podia, Patreon, or YouTube Memberships! This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
Wondering where the best cruising grounds in the world really are? In this episode of The Sailing Doodles Podcast, I break down the pros and cons of sailing in every major region — from the East and West Coast of the U.S., to the Bahamas, Caribbean, Mediterranean, Indian Ocean, Asia, Australia, and the far reaches of Polynesia and the South Pacific. I’ll walk you through: What each region offers (and what to watch out for) Where to go for remote exploration vs. luxury marinas The truth about safety, weather, and bureaucracy My personal favorite sailing destinations Plus, I’ll explain why you don’t hear much about cruising in places like Africa, South America, and China. Whether you’re dreaming of your first bluewater voyage or planning your next big crossing, this episode will help you figure out where in the world YOU should be sailing. Got your own top spot? Drop a comment and let me know where you'd go next. Bobby Host, The Sailing Doodles Podcast Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu #SailingLife #NewBoat #SailingDoodles #IslandSpirit #CatamaranLife
In this special Q&A episode, Bobby answers the questions YOU asked — from the biggest mistakes he’s made at sea to the future of Sailing Doodles, what really happened with Amanda, and what it’s like owning the same classic yacht twice. He also tackles topics like finding crew, dealing with black water, his favorite sailing regions, the future of the channel, and even what dogs and Starlink have in common. Whether you’re a long-time viewer or just discovering Sailing Doodles, this episode is packed with behind-the-scenes insight, sailing wisdom, and a few laughs. Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu #SailingLife #NewBoat #SailingDoodles #IslandSpirit #CatamaranLife
Living the dream on a sailboat or trawler? It’s not just turquoise water and sundowners—there’s a lot of behind-the-scenes maintenance to keep things running smoothly. In this episode of the Sailing Doodles Podcast, we dive into the day-to-day, weekly, and seasonal upkeep every cruiser needs to manage, whether you're crossing oceans or island hopping. We cover Daily checks and troubleshooting Engine, electrical, and rigging upkeep Hull cleaning and anti-fouling tips Tools and spares you should never cruise without Budgeting and when to haul out Tips to stay ahead of breakdowns while off-grid Whether you’re a new boat owner or a salty vet, this episode will help you stay one step ahead of your boat’s needs. Available wherever you get your podcasts or watch on YouTube.
In this episode, I dive into the realities of owning a boat — the good, the bad, and the expensive. I talk about buying back my old CT, what went wrong the first time, and whether it was actually a smart move financially. I also cover the latest upgrades onboard, including my full solar and lithium setup, and whether it’s powerful enough to run the A/C while at anchor. Plus, I share my thoughts on gas vs. electric engines, insurance headaches, bow thruster repairs, and how I’m prepping for my next catamaran. If you’re thinking about owning a cruising boat — or just want to hear the behind-the-scenes of my boating journey — this one’s for you. This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu
In this deep-dive episode of The Sailing Doodles Podcast, we unpack how the sweeping new U.S. tariffs and turbulent global economic conditions are shaking up the sailboat and yacht industry. From massive increases on import duties—jumping from 1.5% to as high as 54%—to buyer behavior shifts and industry-wide production slowdowns, we cover it all. How these tariffs affect popular brands like Beneteau, Lagoon, Ocean Alexander, and more Why U.S.-built yachts are suddenly more attractive than ever How European and Asian manufacturers are reacting—and adapting The impact on both sailboats and motor yachts What it all means for you if you're buying, selling, or just watching the market Whether you're a full-time cruiser, a dreamer in the research phase, or just trying to make sense of what’s happening in the boating world—this episode breaks it all down in a casual, informative way. Subscribe for more sailing insights, market updates, and boat life stories every week. Drop your thoughts or questions in the comments below—how are these changes affecting your boating plans? #SailingDoodles #YachtMarket2025 #BoatBuying #Tariffs #SailingPodcast #SailboatLife #MarineIndustry Blog Post from SV Eoti & Sam Liles: https://sveoti.net/how-high-tariffs-could-drown-the-mid-tier-yachting-world-and-leave-american-cruisers-stranded/ This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/
In this episode of the Sailing Doodles Podcast, we break down what kind of sailboat you can expect to buy at four very different price points: $10,000, $100,000, $500,000, and $1 million. Whether you're dreaming of a cheap fixer-upper, a bluewater cruiser, a luxury catamaran, or something in between, we explore the features, trade-offs, and realities of buying a boat in each bracket. I share real-world examples, ownership tips, and how each tier fits different sailing lifestyles—from weekend warriors to full-time liveaboards. Grab a drink, tune in, and let’s go yacht shopping—from dirt cheap to dreamboat. This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter Phillip@inspiredyachting.com 727-648-0044 https://www.inspiredyachting.com/
Hey everyone – in this Q&A episode, I’m diving into your most-asked questions about sailing life, crew dynamics, future travel plans, relationships, and of course, the pups. We’ll cover everything from: The recent Bahamas travel advisory and onboard safety protocols Amanda, Lauryn, McKenzie... and the real crew drama My thoughts on switching it up with a trawler and the Great Loop Boat costs, upgrades, regrets, and plans for Island Spirit Hull #5 How being a pilot prepared me for life at sea The dogs’ life aboard and how big they’ll get Highs, lows, and what’s really going on behind the scenes Thanks for sending in so many great questions. If I missed yours, drop it in the comments and I’ll catch it next round! Behind-the-scenes and extras: https://sailingdoodles.podia.com
In this episode of the Sailing Doodles Podcast, we dive into the tragic sinking of the Sinbad submarine off the coast of Egypt—what happened, why it matters, and the chilling details. Then we break down all the latest changes in Florida’s boating laws for 2025, and what you need to know if you’re cruising or living aboard in the Sunshine State. Don’t forget to like, comment, and subscribe for more maritime news and sailing adventures!
In this special episode of the Sailing Doodles Podcast, my crew, McKenzie and Clarice, turn the tables and put me in the hot seat! They ask the hard questions about what it's REALLY like to have them onboard, and I share my unfiltered thoughts on their sailing and crewing skills. But it doesn't end there—they also give their brutally honest opinions on what it's truly like to sail and live aboard Nauti Dogs with me as their captain. Expect laughter, candid revelations, and genuine insight into the realities of life at sea. Don't miss this hilarious and heartfelt conversation! Join the Sailing Doodles Navy! https://sailingdoodles.podia.com
Join us in this episode as we dive deep into why Gone with the Wynns made the surprising decision to sell their beloved sailboat! We’ll unpack what this means for their sailing adventures and what's next for this adventurous couple. Plus, explore the exciting world of wind-powered cargo ships and how they could revolutionize maritime shipping, and get an adrenaline boost as we cover the latest from SailGP, sailing's fastest-growing international racing league! Join the Sailing Doodles Navy! https://sailingdoodles.podia.com
In this special Q&A episode, I answer the most burning questions from YOU—our amazing Sailing Doodles community! From my thoughts on single life and past relationships to the future of the channel, the catamaran situation, upcoming adventures, and the realities of life at sea, we cover it all. Join the Sailing Doodles Navy! https://sailingdoodles.podia.com
In this week's boating news update, tragedy strikes at the Imperial Yacht Club Marina as a devastating fire destroys multiple yachts, shocking the maritime community. We also dive deep into the uncertain future of the iconic SS United States—will this historic ocean liner finally meet its end, or is there hope yet? Plus, major shifts in the marina industry as Blackstone acquires Safe Harbor Marinas, potentially impacting thousands of boaters nationwide.Join us as we uncover the full stories behind these headlines, exploring what they mean for boat owners and maritime enthusiasts alike.Don't forget to LIKE, COMMENT, and SUBSCRIBE for weekly boating news, adventure sailing, and much more!#MarinaFire #SSUnitedStates #BoatingNews #Blackstone #SafeHarborMarinasJoin the Sailing Doodles Navy:https://sailingdoodles.podia.com
Ever wondered who actually lives on boats full-time? Are they all retired millionaires, or is it possible for anyone to start cruising? In this video, we break down the REAL stats on liveaboards and cruisers—how much experience they actually have, how they afford it, and the #1 mistake that ends most cruising dreams. We’ll cover:** ✅ The average age of new liveaboards & cruisers ✅ How much sailing experience they have (it’s less than you think!) ✅ Marina life vs. full-time cruising—who actually leaves the dock? ✅ The most common boats for new cruisers (monohull vs. catamaran) ✅ Where first-year cruisers go—Bahamas, Caribbean, or coastal cruising? ✅ How long most people last before quitting boat life ✅ The biggest mistake that ruins the dream for so many sailors
I'm starting a new topic for this podcast. Sailing News! In this episode I cover the recently completed Vendee Globe around the world solo sailing race, the advancement of autonomous and AI powered boats, catch the final ruling on the 3 abandoned vessels of the 2024 Newport Bermuda Race and give you updates of the popular sailing shows like Sailing La vagabonde, SV Delos and Sailing Doodles. Want to support this channel? Join the Sailing Doodles Navy https://sailingdoodles.podia.com
I answer all your questions about sailing with dogs and so much more. Several times a month I takes questions from our patrons and channel members and give it my best shot to answer them all! https://www.patreon.com/sailingdoodles
Should you retire in Thailand! absolutely yes and I will tell you why in this podcast. An Ask Me Anything edition where I answer all my patrons and channel members questions. become a patron https://www.patreon.com/sailingdoodles
I sat down with Captain Glenn Shephard of the Bravo show "Below Deck: Sailing Yacht" at the Annapolis boat show and had a great discussion about his experiences on the hit show! Follow's Captain Glenn's social media to keep up with his adventures Instagram: https://www.instagram.com/capt_glennshephard/ Facebook: https://www.facebook.com/captainglennshephard Support the show by becoming a patron! https://www.patreon.com/sailingdoodles
I answer all the question from my Patrons and CHannel members about my new yacht, the Island Spirit 525e. Its a Sailing electric hybrid catamaran that I am going to sail around the world.
For more info https://www.sailingdoodles.com/island-spirit-525e/
With Burning Man 2024 just wrapping up, I wanted to know how much does the average person spend to go there and what does the Burning Man Organization earn from the festival? Also, how much is spent in total by all festival goers to attend the festival? I answer all these question and more in the podcast.
We spent a week sailing around the Gulf of Naples and the Amalfi Coast in Italy and I give you my opinion on what it is like. From the costs, to the sights, I give you the run down on Italy
Rick Doblin is the founder of MAPS (multidisciplinary association for psychodelic studies), which just complete phase 3 trials for using MDMA to treat PTSD. They have an astounding success rate curing PTSD with 67% and addition 21% seeing good progress towards healing... thats 88% success in helping people live better lives. https://www.maps.org
I answer all of our patron's questions including: Should I get my medical back and fly part time again? Would you like to have your question answered on one of our Ask Me Anaything segments? Become a patron!
https://www.patreon.com/sailingdoodles
Link to the pay per view video: https://www.sailingdoodles.com/bvi-movie-final/
Link to my new catamaran Island Spirit 525: https://navigare-yachting.com/en/yacht-ownership/new-yachts/island-spirit/island-spirit-525-nn/209?ny=4163
Link the the Croatia Flotilla: https://navigare-yachting.com/en/events/other/join-sailing-doodles-on-a-croatia-yacht-charter-with-navigare-in-july-2024
I sit down with Dr. Shawna Pandya and discuss how the effects of space on the human body and how advances in space medicine will dictate the future of crewed space expoloration.
Dr. Shawna Pandya is a scientist-astronaut candidate with Project PoSSUM, physician, aquanaut, speaker, martial artist, advanced diver, skydiver, pilot-in-training, VP Immersive Medicine with Luxsonic Technologies and Fellow of the Explorers' Club.
I sit Down with Amanda and discuss what type of cruising life is better, by boat or RV? We have spent a good amount of time in each mode of transportation so its time to discuss which we like better
Link to the pay per view video: https://www.sailingdoodles.com/bvi-movie-final/
Link to my new catamaran Island Spirit 525: https://navigare-yachting.com/en/yacht-ownership/new-yachts/island-spirit/island-spirit-525-nn/209?ny=4163
Link the the Croatia Flotilla: https://navigare-yachting.com/en/events/other/join-sailing-doodles-on-a-croatia-yacht-charter-with-navigare-in-july-2024
I address the negativity that my most recent video received from viewers in the comment section. People make a lot of assumptions without knowing all the facts, so I did my best to give them the proper information
Link to the pay per view video: https://www.sailingdoodles.com/bvi-movie-final/
Link to my new catamaran Island Spirit 525: https://navigare-yachting.com/en/yacht-ownership/new-yachts/island-spirit/island-spirit-525-nn/209?ny=4163
Link the the Croatia Flotilla: https://navigare-yachting.com/en/events/other/join-sailing-doodles-on-a-croatia-yacht-charter-with-navigare-in-july-2024
I had a chance to sit down at the Miami Boat Show with David Levesqu, the Editor of Latitudes and Attitudes Magazine. We discussed the cruising life and his magazine!
I sit down with Phillip Winter, the Sales Manager for Navigare Yachting a the Miami boat show to discuss yacht ownership and how you can earn guaranteed income on the boat by putting it in charter. Navigare Yachting has one of the largest charter fleets in the world with bases all over the globe.
Link to Yacht Ownership:
https://navigare-yachting.com/en/yacht-ownership/new-yachts?ny=4163
Link to more info on the Island Spirit 525:
https://navigare-yachting.com/en/yacht-ownership/new-yachts/island-spirit/island-spirit-525-nn/209?ny=4163
Link to Yacht Charter:
https://navigare-yachting.com/en/services/bareboat-yacht-charter?ny=4163
I answer probaby the most asked question we get.... Should you cruise in a catamaran or a monohull? It's honestly a very tough question to answer but I have a lot of experience on both types of boats and give the best insight as I can! I also answer all of our patron's question! If you would like your question answered please become a patron at https://www.patreon.com/sailingdoodles
for more information about the miami boat show, please RSVP at:
https://docs.google.com/forms/d/e/1FAIpQLScVyJuA8hngq2IHFQcWJDA-9kQ62ePXW2eZIuRfNssAYMwPeA/viewform
For more information about the Island Spirit 525e, visit:
https://navigare-yachting.com/en/yacht-ownership/new-yachts/island-spirit/island-spirit-525-nn/209?ny=4163
I ask Amanda what she thinks about being a sex symbol on Sailing Doodles. Does she hate it or love it? She lets you know!
Sign up to for the Miami boat show happy hour and meet up! https://docs.google.com/forms/d/e/1FAIpQLScVyJuA8hngq2IHFQcWJDA-9kQ62ePXW2eZIuRfNssAYMwPeA/viewform
It another Ask Me Anything episode where I answer all our patrons questions. If you'd like to have a question answered become a patron at https://www.patreon.com/sailingdoodles
In this podcast the main topic is that we are looing for new crew!
Vlogs across the board have been in decline over the past 3 years for several reason. In my opinion it is beacuse of youtube's preference for Shorts, new Ai technology and IP Theft from bad actors
I sit down with crewmate Amanda Zakri and our patrons ask her anything! From her personal life to professional life, Amanda tells it all! Amanda is an actor and has her own youtube channel @AmandaZakri. So lets have fun and talk to Amanda!
Meet my new "brother" Murphy, He's a cock-a-poo puppy and so cute! I also answer all the questions from our patrons about sailing doodles, the crew and the future of the show!
Amanda Sailed with me back in 2017 for 3 months or so and now she's back! Find out what she has been up to and why she decided to come sailing with me again.
I answer all your wuestions about Sailing Doodles and sailing in general. My patrons want to know if we are going to sail a circumnavigation.... what do you think? Should we sail around the world? Want to get your questions answered on the next podcast become a patron at https://www.patreon.com/sailingdoodles
I answer all the Sailing Doodles Patrons and members questions about the sailing and cruising life. Specfically, What is the hardest thing to give upo for the sailing and cruising life? Such a good question and I hope I answered it well!
Well my new sailing Cat Island Spirit 525 has been delayed and I likely won't get it until next summer. I need something to sailing the mean time so I am buying a used Sea Ray to scream around the bahamas for 4 months! Does it sound like a good time?
I tell you how and why we ended up in Mexico. We had such a good time down there. It is a beautiful place and the people are so warm and friendly. It's too bad about how corrupt the government is and the crime. We almost were held for ransom or went to prison just for making a wrong turn. This is my story.
I sit down and talk with Dakota who is the new host of Flying Doodles on Youtube. Its the show where we interview airplane owners about their planes,strap a few gopros on the plane and then go fly! So please welcome Dakota!
I give you my thoughts on my sailing experiences sailing around Greece this summer for 3 months. There good and the bad, it was still worth it!
I have been going to burningman for 10 years and was in attendance this year, 2023, also. I give you the real life behind the scenes scoop on what it was like at burnginmany during the rain event and what everyone did to cope with it. It was not nearly as bad as the media is hyping it up to be.
I interview Darryl from Precision Sails and Ben from the Youtube show Breaking waves.
Visit SailingDoodles.com to find out more information about us!
I interview Todd about his racing career and his brand new line of side by side utvs SpeedUTVs.com @theromaniak @speedutv
Visit Sailingdoodles.com
I answer all my patron's questions about Sailing doodles and sailing in generally. Specifically in this episode we hone in on a lot of crewing questions.
Visit Sailingdoodles.com
Stephanie and I sit down and have a chat about whats been going on with sailing doodles and what is next!
I can't believe I have been banned again from facebook! Check out SailingDoodles.com to help out the show!
All of the sailing vlogs are in a slump? Is this the end of the sailing vlog era?
Support this show by becoming a patron! https://www.patreon.com/sailingdoodles
Yes that's right, my entire Facebook platform was demonitized for 90 days and there is nothing I can do about it.
To help support the show you can go to Patreon.com/sailingdoodles
I talk with Stephanie @psychodelicdaydream about our time sailing around in Greece and give you all the info you need to know! Its such a great place and we are happy to share the details about it here is the link for "The Cruising Life" http://gcsf.gnosishosting.net/Events/Info/The_Cruising_Life_By_Bobby_White-4517
I interview fellow cruisers Jan & Keli that have been crusing for a year on their Lagoon 45 catamaran with their two kids, 15 &9 years old.
@kelibirdy
@janthe3rd
I answer all the Sailing Doodles Patrons Question and give you the top 5 Anchorages in the BVI
I give you my feedback on what it has been like living full time on a motor yacht for 1 year now.
visit SailingDoodles.com to support the show!
I give you the scoop on what's ahppening at sailing doodles and give you some info about the new sailing class i am offering.
Meet Stephanie Sinka, the newest crewmember on Sailing Doodles. We go in to her background and how she came to join the show.
A timeline of how Covid affected out cruising and other cruisers as well as how it looks for the future of cruising
https://www.patreon.com/sailingdoodles
I answer all the Sailing Doodles Patron's questions! If you would like to have your question answered in next month's edition of Ask Me Anything then head over to: https://www.patreon.com/sailingdoodles thank you for watching!
I go through all the pluses and minus of sail and power boats, compare them and give you my opinion as to which is better
https://www.patreon.com/sailingdoodles thank you for watching!
I answer all the Sailing Doodles Patron's questions! If you would like to have your question answered in next month's edition of Ask Me Anything then head over to: https://www.patreon.com/sailingdoodles thank you for watching!
I talk with Sydney who is crew on Sailing doodles and a nomad adventurer at heart.
@thesaucewithsyd on instagram
I talk with Taylor of Taylor's Travels and also a Sailing Doodles Crew memeber. She is a solo female sailor and cruiser and has a very succesful YouTube show called "Taylor's Travels".
I speak with Carlos Ponce, who is the Sales and Customer Service Manager for Marina Puerto Del Rey in Puerto Rico. We discuss why Puerto rico is such a good launching point for the Caribbean.
@MarinaPuertoDelRey
@SailingDoodles
Patreon.com/SailingDoodles
I answer all the Sailing Doodles Patron's questions! If you would like to have your question answered in next month's edition of Ask Me Anything then head over to: https://www.patreon.com/sailingdoodles thank you for watching!
I talk to zack and great about how boat finance work. you can visit their site at AzulMarineLending.com
SailingDoodles.com to support the show
Meet Sailing Doodles member and Eternal Fleur founder & CEO Amanda Wojtas. We talk sailing,cruising and having a good time
eternalfleur.com
visit sailingdoodles.com to become a patron and support the podcast
Meet Sally and Silvie, who are identical twins and full time liveaboard sailors. They have a non-profit Sponsors of Hope at SponsorsOfHope.org and follow their social media @sponsorsofhope
We meet with Diana Margarita who represents many Puerto Rico Marinas, and is hosting match racing in puerto rico. We have a great discussion about Puerto Rico and why its such a great place to sail.
We talk with Great and Zack about how boat finance works.
To Contact them:
Zack 941-961-9477 (english)
Greta 941-536-3866 (italian & Spanish)
web azulmarinefinance.com
Support the podcast:
https://www.patreon.com/sailingdoodles
Meet the newest crew member to join Sailing Doodles!
Taylor's Instagram:
@taylorFrancis_
Want to support this channel?
Https://www.patreon.com/sailingdoodles
Ever Thought of starting a Vlog or YouTube Channel? Listen to this first!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We discuss the various options and cost of having communications and internet while cruising.
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We interview YouTube Star Dylan Magaster about how he bought a 25 year old van, converted it to a living space and then travelled most of north America. You can check out his YouTube Channel at:
https://www.youtube.com/user/Dylanmagaster
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We talk about cruising the Caribbean and hopefully you can decide if it is the right place for you to start cruising!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We give our opinions on what it is like to cruise the bahamas and hopefully you can decide if it is the right place for you to start cruising!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
Catamaran or Monohull? It's a hot debate right now and the trend is toward catamarans... What should you buy and which is better?
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We Discuss the day to day life and what it is like living on a boat!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
Are you ready to go cruising? How long until you are ready and what do you need to do to get ready? We answer all these questions and more!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
Many people think that sailing is a solitary endeavor but that is far from the case! In this episode we explain how much fun and complex the cruising social life can be!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We give from our experience the cost of cruising. From provisioning, repairs, and shore excursions it can all add up pretty quickly but if you do it right it can be very affordable.
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We discuss what it is like to cruise via sailboat with pets. We include all the legal requirements most countries have and all the things you have to take into account when sailing with animals!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/
We introduce ourselves, Bobby and Laura, and describe our journey around the world with two full size labradoodles!
This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron for as little as $1 per week. Visit:
http://www.sailingdoodles.com
or
http://www.patreon.com/sailingdoodles
Donate Via Paypal to help us get a new drone:
http://www.paypal.me/sailingdoodles
Check out the guys that made this voyage across the pacific possible by giving us this awesome boat to sail:
Gulf Charters Thailand
http://www.gulfchartersthailand.com/
Sailing School
http://www.sailingschoolthailand.com
Island Spirit Multihulls
http://www.islandspirit-catamarans.com/