Key Takeaways
- When you travel for a living, you get asked a lot of questions as you bounce from one hostel to another. The top one: what’s your favorite country?
- The second most asked question: what’s your favorite city?
- I’ve spent a long time traveling the world and have been to hundreds upon hundreds of cities in the world. There are so many that I love for many diff
When you travel extensively, you’re often asked two questions: what’s your favorite country — and what’s your favorite city?
Having visited hundreds of cities across six continents, I’ve found that the ones that resonate most aren’t always the flashiest or most famous. They’re places where energy aligns — where rhythm, people, and atmosphere click with your own. Places where you think, “I could live here.” Not just pass through, but truly belong.
That feeling — of ease, familiarity, and deep connection — is what defines these 14 standout cities. Here they are:
1. Amsterdam
I’ve visited Amsterdam more times than I can count — easily over a dozen. For a few months in late 2006, I even lived there while working as a professional poker player (yes, really!).
What keeps me returning? Its vibrant pace, welcoming locals, seamless access to the rest of Europe, photogenic canals, and striking architecture. And yes — its famously eclectic spirit adds layers of surprise and delight.
In many ways, Amsterdam echoes my hometown of Boston — brick-lined streets, brisk energy, and understated charm — making it feel like a second home.
Favorite activity: Renting a small boat and drifting through the canals with friends.
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2. Paris
My first walk down the Champs-Élysées sealed it: Paris was everything I’d imagined — and more. Yes, it’s large, expensive, and crowded with visitors. But so are many great global capitals — and Paris transcends those challenges with effortless elegance.
Its beauty is layered: centuries of history, world-class cuisine, artistic legacy, and an unmistakable joie de vivre. In 2019, I spent several months living there — and discovered that its magic deepens the further you move beyond postcard-perfect landmarks into neighborhood cafés, markets, and hidden courtyards.
Favorite activity: Assembling a simple picnic — fresh baguette, cheese, fruit, and wine — and enjoying it beside the Seine.
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3. Bangkok
My early impressions of Bangkok were harsh — polluted, chaotic, overwhelming. It wasn’t until I lived there that I began to see its soul.
Bangkok reveals itself slowly. It’s not built for short visits — it’s built for living. Once settled, you’ll find endless energy: dynamic live music venues, legendary street food stalls, warm communities, and a pace that’s both relentless and deeply hospitable.
This city taught me that first impressions can mislead — and that meaningful discovery requires time, openness, and willingness to look past surface-level chaos.
Favorite activity: Catching indie bands at Brick Bar or slurping steaming bowls of noodles at a family-run stall after midnight.
For travelers heading to Bangkok, Route for Less’ full budget travel guide offers curated recommendations, transport tips, and insider strategies — all in one practical resource.
4. Stockholm
I’ve long admired Scandinavian design, lifestyle, and values — and Stockholm embodies them all. I’ve returned multiple times over the years, even attempting to relocate there once (though logistics didn’t pan out).
Few cities rival Stockholm’s visual harmony: red-brick facades, emerald waters, archipelago vistas, and golden-hour light reflecting off centuries-old stone. In autumn, the interplay of crisp air, fiery foliage, and historic architecture creates something quietly magical.
