Last Updated: 5/10/21 |May 10th, 2021 (Originally 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:
My 14 Favorite Cities
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!
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 some good food at the market and having a picnic.
Get my complete budget travel guide to Paris and plan the perfect trip! It’s hundreds of pages long and will help you plan the best trip there!
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, wonderful food (nothing beats Thai street food), and even more wonderful people. It’s just a bad tourist city. There’s just not a lot to do there for a tourist. It’s a city you live in.
Living in Bangkok showed me that looks can be deceiving and that there is more to a city than what you see on the surface. You just need to be willing to look a little deeper.
And, when you do, you always find something special.
Favorite activity: Live music at Brick Bar or eating noodles at a street stall.
If you’re visiting Bangkok, check out my complete budget travel guide to Bangkok! It has everything I know about the city in one easy place.
I think this city is one of the most picturesque 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, with a high quality of life, and the Swedes in the city are super friendly and welcoming. It’s not a cheap city to visit, but it’s worth every penny!
Favorite activity: Getting lost in the maze of historic streets in Gamla Stan.
5. New York City
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 multicultural 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.
I love NYC. It is the heart of the world to me. It is a non-stop place where you come to make it in the world. You can always find something to do, world-class food, people from all walks of life, and just a hustler vibe.
I spent close to five years living there and visit at least once a month (when I can).
It is the city you see in the movies.
Favorite activity: Walking the High Line and cooling off with drinks at the Grey Mare.
Since I spent so much time there, I wrote a budget travel guidebook to New York City! Pick it up for all the insider info you need!
After NYC, Chicago is probably my favorite US city, especially in the summer time.
While the winter months here can be brutal, this lakeside city seems to come to life after it emerges from its long and cold winter. Along with its lively atmosphere, the food here is delicious and the architecture is second to none. There’s a vibrant energy during the summertime as everyone is out in the parks, cafes, rooftop bars, on the lake, and watching the Cubs.
Chicago is just awesome.
Favorite activity: Going to a Cubs game!
For more, read our destination guide to Chicago and start planning your trip today.
I think this must be one of the most livable cities in the world. I’d certainly live in it, which is my benchmark for whether or not I really 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.
Not only is there incredible nature nearby but 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. It’s not a cheap city to live in, but that’s the price for all the amazing things Vancouver has to offer!
Favorite activity: Hanging out on Granville Island or walking around Stanley Park.
Perched on a lake in the stunning South Island mountains of New Zealand, Queenstown is a high-energy resort town for adventurers. This isn’t your typical city, as travelers come here because they want to be outside. There’s bungy jumping, hiking, rafting, zip-lining, boating, and tons more. It’s a paradise for the outdoorsy type and the perfect city for people who don’t like big, crowded cities.
The city and surrounding area are postcard-perfect (much like the rest of the country! I would jump on a plane and head back there right now if I could.
Favorite activity: Hiking the surrounding mountains.
Read our guide to Queenstown to plan your next adventure there.
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 and for the fact that it’s on the water and has a fun nightlife.
Not only that, but Perth is the perfect jumping-off spot to see the western Australian parks and natural sites, and it’s also close to hip Freemantle, which is home to my favorite Australian brewery: Little Creatures. I find it much more personal than other towns in Australia.
Favorite activity: Relaxing at the beach
10. Hong Kong
Hong Kong is one of the best cities in the world for foodies. I always stop in when I’m in Asia and stuff my face with some of the best dumplings in the world. The city is busy and dense (it’s one of the most densely populated places on the planet) but it has a fun nightlife and tons of activities to keep you entertained, from markets to temples to nearby hikes outside the city.
While the city offers an interesting mix between eastern and western cultures, what really sets Hong Kong apart from other massive, dense cities is just how clean and well-organized it is. Getting around is a breeze, making it an easy and fun place to explore for a few days — or more!
Favorite activity: Eating dumplings!
Iceland is one of the most expensive countries in the world. As a budget traveler, you’d think that would keep me away but let me tell you something: it’s absolutely worth the price.
Reykjavik has tons of cozy cafes, wild clubs, cute architecture, and friendly pubs. It’s tiny, yet you can easily spend a few days here and not get bored (especially if you’re a night owl. Icelanders love to party).
Fortunately, as the tourism industry grows, there are more and more free (or cheap) things to do in the city. And with Icelandair offering free stopovers on flights between North America and Europe, it’s never been easier to visit this charming Scandinavia capital.
Favorite activity: Cozying up in a cafe to read and people watch.
As a history nerd, I’ve always loved visiting London. Some of the best museums in the world are there — and they are all free (there are tons of other free things to see and do as well).
But it wasn’t until last year when I spent a month in the city that I really “got” it. I understood why people loved it. There was a charming sophistication to the place.
Strolling the streets of the city, enjoying the markets, taking in the history of the place, laying in the park, and having a pint outside a pub? Heaven.
Paris will always have my heart but London comes close.
Favorite activity: Visiting as many museums as I can and then drinking at a pub.
Check out our travel guide to London to plan your trip.
Oaxaca, a city in the central part of the Pacific coast of Mexico, is a hub for heritage tourism, owing to its many historical attractions (including Monte Albán, a UNESCO Heritage Site; and Mitla, a Zapotec archeological site), colorful buildings, scenic rooftop restaurants and bars, street art, historic Spanish colonial churches, cobblestone streets, and many parks.
The city has everything I like: history, Mezcal, and food. Oaxaca is one of the gastronomic centers of Mexico and was the place I fell most in love with during my visit to the country. It’s safe, the people are wonderful, the buildings are beautiful, and the food…did I mention the food? It’s out of this world.
Within seconds of landing here, I knew I belonged. I could easily live here I love it so much.
Favorite activity: Visiting the mezcalerías.
14. Cape Town
Cape Town is one of those places I can never get enough of. Its natural beauty, climate, people, chill atmosphere, and delicious food scene always make my visits memorable. Head up Table Mountain and Lion’s Head to soak up the city’s iconic view, walk the famous boardwalk along Muizenberg Beach, and visit the Robben Island prison where Nelson Mandela spent 27 years behind bars. Also, don’t miss the penguins at Boulder Beach. They’re super cool.
Favorite activity: Relaxing on the beach!
Check out our travel guide to Cape Town to plan your trip.
There are you have it! My favorite cities in the world. Leave a comment on this post and let me know what your favorites are – and why!
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
- SafetyWing (best for everyone)
- Insure My Trip (for those 70 and over)
- Medjet (for additional evacuation coverage)
Want to Travel for Free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodation — all without any extra spending. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.
Need Help Finding Activities for Your Trip?
Get Your Guide is a huge online marketplace where you can find cool walking tours, fun excursions, skip-the-line tickets, private guides, and more.
Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.