1 Boston | United States | History nerd in running shoes who accidentally learned to like good food. | About 650k in the city; ~5M in the metro. | T is creaky but covers the basics; insanely walkable core; bike network getting less terrifying each year. | Still my baseline city: high ceiling on walkable neighborhoods and low ceiling on winter happiness. Feels like a college campus that turned into a whole metro area. |
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2 New York City | United States | Main character energy turned into a five-borough shared delusion. | About 8.5M in the city; ~20M in the metro. | Subway is chaotic but omnipresent; you can live car-free and still forget what a steering wheel looks like. | Every time I visit I decide to move there for exactly 36 hours, then see rent prices and scuttle back to Boston like a crab with student loans. |
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3 Chicago | United States | Big-shouldered extrovert who actually remembers your name. | Roughly 2.7M in the city; ~9.5M in the metro. | L is solid in the core, buses fill in the grid, and the city actually understands what a bike lane is. | Feels like the Midwest built a proper coastal city as a group project. If you fused Boston’s density with friendlier people and cheaper rents, you’d get something suspiciously Chicago-shaped. |
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4 Montreal | Canada | European weekend packed into a North American body with poutine in both hands. | About 1.8M in the city; ~4.3M in the metro. | Metro is clean and logical, biking is fantastic in warm months, and walking + cafés is basically the local religion. | My favorite "I need to feel like I traveled far without actually doing that" city. Perfect for pretending you’re sophisticated while still paying in dollars that mostly feel like dollars. |
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5 Portland (Maine) | United States | Chill coastal town that min-maxed food and scenery instead of size. | About 70k in the city; ~500k in the metro. | Walkable downtown and waterfront; buses exist but this is mostly a feet-and-uber type situation. | My go-to escape hatch when Boston feels loud. Great beer, ridiculous seafood, and the kind of streets that make you consider buying a notebook and becoming “a writer.” |
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6 Seattle | United States | Tech wizard in a fleece who power-walks between coffee and trailheads. | Around 750k in the city; ~4.1M in the metro. | Light rail is finally useful, buses are solid, and hills make you earn every walkability point. | Feels like Boston’s outdoorsy cousin who discovered microdosing and better mountain views. I could absolutely live here if I ever start taking vitamin D seriously. |
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7 Austin | United States | Live-music extrovert trapped in a rapidly sprouting tech campus. | Roughly 980k in the city; ~2.5M in the metro. | Bus-heavy and car-heavy; light rail is a work in progress, so rideshares are doing a lot of cardio. | Every time I’m there I bounce between “this is a playground” and “this is what happens when zoning laws take a nap.” Elite tacos, questionable summers, vibes off the charts. |
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8 Copenhagen | Denmark | Minimalist fairy tale where bikes outnumber bad design choices. | About 650k in the city; roughly 1.4M in the metro. | Bikes rule everything; metro is clean and frequent; walking feels like touring a Scandinavian UX demo. | This is my urban-planning crush. Whenever Boston adds a new bike lane, I’m like, “Look at you, trying to be Copenhagen when you grow up.” |
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9 Tokyo | Japan | Hyper-dense fever dream that’s somehow the most orderly chaos on Earth. | Roughly 14M in the 23 wards; around 37M in the greater metro. | Transit system is a literal boss battle of complexity but runs like a perfectly timed speedrun; walking is endless micro-neighborhood discovery. | If you like cities as systems, this is the final level. Every time I read about Tokyo I want to print transit maps and hang them like posters above my bed, which is a normal thing that normal people do. |
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TheLysts
