My Favorite Cities in the World

Amsterdam

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). The fast-paced life, friendly locals, easy access to the rest of Europe, picturesque canals, and great architecture keep me coming back. In some ways, Amsterdam reminds me of my hometown of Boston, which might be why I love it so much. Either way, I never step foot in Europe without making plans to go there.
Favorite activity: Boating through the canals with friends.
Get my complete budget travel guide to Amsterdam here.
Paris

Ever since I stepped out on the Champs Elysees, I knew Paris was it. I was in love. It had that “je ne sais quoi” that people talked about, and I was unable to ignore its magic. Sure, Paris is large and expensive, and the people can be rude. But what big city isn’t like that? Paris is just too beautiful, vibrant, and filled with great food and history. Being here is like being in a real life romantic comedy, but better.
Favorite activity: Picking up some good food at the market and having a picnic.
Get my complete budget travel guide to Paris here.
Bangkok

I hated Bangkok the first few times I traveled there. It was simply a dirty, polluted city with no redeeming qualities. It wasn’t until I moved there that I fell in love with it. Bangkok, it turns out, is an easy city to live in – there’s lots to do, plenty of events, great bars (Cheap Charlies), wonderful food (nothing beats Thailand street food), and even more wonderful people. Plus, it’s easy to get around. Bangkok showed me that looks can be deceiving, and that there is more to a city than what is on the surface. I loved my time living there.
Favorite activity: Gin and tonics at Cheap Charlies.
Get my complete budget travel guide to Bangkok here.
Stockholm

I have a strong affinity for all things Scandinavian, and Stockholm is no exception. I’ve been there three times, and am considering moving there next summer to learn Swedish. I think this city is one of the most beautiful I have ever seen. The reds and greens of the buildings have an old world charm that rivals cities like Prague, and, during the fall, the changing leaves only highlight that beauty. Stockholm is also very historic, has a high quality of life, and the Swedes in the city are super friendly and welcoming. I’ve been 3 times already.
Favorite activity: Getting lost in the maze of historic streets.
Get my complete budget travel guide to Stockholm here.
New York City

I never really liked New York until after I lived in Bangkok and got used to big city life. Now, whenever it is I decide to move back to the United States, I will move to New York City. I lived there last summer and came back every other week between trips around the U.S.  New York City is a place where dreams are made into reality, and there is always something to do, something to see, or a new place to eat.  The city is so multi-cultural that when I feel like I need to travel but I can’t, there’s an ethnic area of the city that will give me my fix. Moreover, it’s constantly stimulating. And, as someone who can’t sit still very well, it’s perfect for me.
Favorite activity: Walking the High Line and cooling off with drinks at The Frying Pan.
Get my complete budget travel guide to New York City here.
Chicago

After NYC, Chicago is my favorite U.S. city. In the summertime, there is just something about Chicago that draws me. This lake-side city seems to come to life after it emerges from its long and cold winter. Along with its lively atmosphere, the food there is delicious and the architecture is second to none. I’ve only been there twice and haven’t seen much of the city, but I like what I have seen. I never get bored of visiting Chicago.
Favorite activity: Cub’s game!
Vancouver

I think this must be one of the most livable cities in the world. I’d live in it, which is my benchmark for whether or not I like a place. In Vancouver, you can go from the city into the mountains in minutes. I think that is really the highlight of the city for me – the fact that I don’t have to go far to be with nature. Moreover, there’s a park so big in the middle of the city, I often feel like I am in the center of a forest. Add in a vibrant food and art scene, and Vancouver is definitely a world-class city.
Favorite Activity: Hanging out on Granville Island or walking around Stanley Park (tie).
Queenstown

Perched in the stunning south island mountains of New Zealand, Queenstown is a place for adventures. There’s bungy jumping, hiking, rafting, zip lining, boating, and tons more. Travelers come here because they want to be outside. Situated on a lake near the Remarkable mountain range, Queenstown is a high-energy resort town. It’s small, prettier than a postcard, and perfect for people who like the outdoors. I would jump on a plane and head back there right now if I could.
Favorite Activity: Hiking in the surrounding mountains.
Perth

Perth, Australia is more like a big town than a city, and I think that’s what I like about it. It’s big enough to have a lot to do, but small enough to feel cozy. I love Perth because of that small town, big city feel, the fact that it is on the water and has great nightlife, that it’s a great jumping-off spot to see the western Australian parks and natural sites, and that it is close to hip Freemantle, which is home to my favorite Australian brewery, Little Creatures. I find it much more personal than other Australian towns.