When we had some calm seas while I was on the Drumfire, with my schedule unusually clear and Starlink humming, I found myself writing Python with Claude to export and analyze all of my Swarm check-in activity. I have 14,021 check-ins. So now on my about page it lists the ~70 countries I’ve been to and the top 200 cities I’ve spent time in. But it made me think a lot about what my favorite cities are, so here are my top ten current faves, in no particular order:

  • Paris
  • Tokyo
  • Sydney
  • Florence
  • New York
  • San Francisco
  • Stockholm
  • Singapore
  • London
  • Houston

Any of these I would be happy to live in. Honorable mentions but didn’t make the cut: Austin, Jackson, Seattle, Copenhagen, Los Angeles, Washington DC, Montreal, Vienna, Reykjavik.

I would be remiss if I didn’t use this as an opportunity to highlight Paul Graham’s great essay on Cities and Ambition.