Best Cities

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.

23 thoughts on “Best Cities

  1. Great list. I enjoyed a couple weeks in Paris after Italy. Actually visited Copenhagen and Reykjavik after that. I had already been to Reykjavik but it was my first visit to Copenhagen and it exceeded my expectations.

    I’m curious what you thought of Torino and if you had visited it before WordCamp Europe? I have to say I found it highly underrated and I loved my extended stay in the city center which was extremely walkable and with a lot of parks and green areas.

    I met people at WordCamp who were actually taken back when I mentioned how much I was enjoying it there… they were staying in a hotel near the venue and hadn’t even visited the city center. They only saw the industrial area (in the process of being revitialized) where the venue was and had no clue how great it was just a few minutes north of there.

    1. I was really impressed with Torino, too, and would agree that it’s a “sleeper” people don’t talk about much but that is lovely in so many ways. While I was there, I got to meet with the Elkann family, who have deep roots in the region, and I can see why they love and invest in it.

      It goes to the heart of philanthropy; really, how can you invest in making things better around you for future generations to enjoy? I get a deep sense of that in Italy. Though in many places they’re building on the beauty of the land, like in Capri, where some other cities build beauty in spite of the land, like a New York or Tokyo.

      1. I agree. It’s a city I’ll definitely be returning to as I have unfinished business when it comes to exploring northern Italy.

        I would also say I think it would be great if WordCamp Europe could look at trying to seek out these kinds of “sleeper” cities in the future for the host city of the event.

        Although I just admit I’m really looking forward to Basel. I was supposed to visit Switzerland after WordCamp Europe and had been invited to visit the Omega headquarters in Biel/Bienne but the weather in that part of Europe was not cooperate and heavy rains and flooding was causing travel issues so we changed things up and went to Copenhagen and Iceland instead.

        The Basel event gives me another shot at the Onega headquarters visit… they don’t usually extend them… and I can’t wait!

  2. Thoughts on San Diego?

    I was just passing through and haven’t left yet… however many years later! WordCamp was downtown the other year which was awesome, and the weather! But mostly Ocean Beach. It truly is a different place than anywhere else I’ve been in the world.

    If you’re ever passing through, Matt, I’ll buy you a coffee and introduce you to the people whose lives are the better for being here, and being introduced to WordPress ❤️

    1. It was uncanny! Python seems to be what the AIs default to writing code in, not sure why. Probably someone set a flag somewhere and now we all use it. 🙂

    1. Looks like I did in 2013: saw the Jazz Bar, Waldorf Astoria, St. Cuthbert’s Parish Church, St. Mary’s Cathedral, Scottish National Gallery of Modern Art, Camera Obscura, and ended at The Queen’s Arms. Maybe time to revisit!

    1. That’s a tough one! Cities often experience growing pains, such as the traffic in Jakarta or Manila. One thing I deeply believe, though, is you can find great spots almost anywhere; there are pockets of awesomeness in cities that many would overlook. Luckily, with the WordPress community, I have local connections almost everywhere!

  3. I feel like a “Country Bumpkin”… I’m a British/Canadian Citizen, have been to Houston, and none of the other cities mentioned.

    BUT…I know Vancouver, BC, intimately. I spent a lot of time in Whistler 50 years ago.

    I mean it when I say I live in Heaven…an accident paralysed my left side and I landed softly in a gorgeous place in the Olympic Village half a block from the ocean.

    Socialist Canadian? Of course I am!

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