My 12 Favorite Cities In The World (Updated 2019)

Updated: 8/4/2019 | August 4th, 2019 (Orignally posted in 2011)

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 different reasons – some for art, some for history, some for the food, most for the people.

But, to me, the ones that stand out the most are the ones where I feel most at home. They are places I visit and feel connected too. Their energy and my energy match. I move around them with ease, I feel at one with the culture, and tempo of the city.

I think to myself “Yeah, I could live here.” Not just visit but live.

And, when I think that, then I know I’ve found a special place.

So what are my favorite cities in the world? Where are the places I feel that way? They are here:


1. Amsterdam

The historic buildings of Amsterdam that line the narrow canal

I can’t say exactly how many times I’ve been to Amsterdam, but it’s in the double digits. And, for a brief time at the end of 2006, I lived there as a professional poker player (Seriously. It’s one of the more interesting random facts about me!).

The fast-paced life, friendly locals, easy access to the rest of Europe, picturesque canals, and stunning architecture keep me coming back. Plus, it being Amsterdam and all, there are tons of weird and quirky things to see and do there too!

In some ways, Amsterdam reminds me of my hometown of Boston, which might be why I love it so much. The brick buildings, fast-moving people, austere vibe. It feels like home.

Favorite activity: Boating through the canals with friends.

Visiting Amsterdam? Check out my complete budget travel guide to Amsterdam! It’s hundreds of pages long and will help you plan the best trip there!

2. Paris

A Eiffel Tower on a bright, sunny day in Paris, France

Ever since I stepped out on the Champs Elysées, I knew Paris was it. It was everything I dreamed it would be I was in love from the first moment. Sure, Paris is large and expensive and bursting with tourists. But what big city isn’t like that?

Paris is beautiful, vibrant, and filled with tasty food and history. Being here is like being in a real-life romantic comedy. I love the city so much I even moved there for a good chunk of 2019. It really does live up to all the hype, especially when you move away from the tourist areas and into the local places more.

Favorite activity: Picking up…

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