As a digital nomad — someone who travels constantly while working remotely — I've gotten to live in quite a few cities. I've also gotten to see the best cities to live in in a different way than you might if you just went there for vacation. I've experienced what it's like to couch surf, club, grocery shop, jog, go to business meetings, get your phone repaired, and get lost in many different parts of the world. So, I thought I'd pass on my knowledge by ranking the places I've been so far.
This list is by no means exhaustive; my travels have been mainly limited to major cities in the United States and western Europe. I'm also going to exclude a lot of places I've been, because if your entire visit was spent in a hotel or a festival an hour away from it (hi, Vegas) or you just stopped there for multiple layovers (hey, Reykjavik) — even if you sneaked out of the airport before your connecting flight (what's up, Barcelona) — it doesn't really count.
So, here are some of the cities I've lived, worked, and played in — and how I'd ranked them for living, working remotely, and playing.
1New York, NY
Living: You probably don't need me to tell you that New York is one of the most expensive and annoying cities to live in, and you get very little for your money. Of course, though, there's a reason for that: Everyone wants to live there. You will never run out of places to go or things to do. The only risk is falling victim to the paradox of choice and spending the night in your apartment Yelping places you never make it to.
Working: Given the endless places to work in, being a nomad in New York is surprisingly annoying. Cafes are crowded, bathroom lines are endless, and some places are stingy with WiFi, making you buy more cold brew coffee and artisanal donuts every few hours to stay online — because rent is damn expensive for the owners, too. That said, it's New York. You can always find what you need within a 10-minute walk at almost any hour (and if what you need is a place to work, hotel lobbies are great for that, too). Not to mention, you can find endless meetups and events for your industry, no matter what it is. If you find yourself in New York, take the opportunity to network, because you won't have access to that many people again for a while.
Playing: New York social life is pretty centered around bars. There's still a ton to do if you don't drink, but you have to proactively look for it, because your friends will probably suggest bars. The club scene seems decent if you're from the United States, though will look inadequate once you've been to Europe. The one thing New York is never lacking is concerts. You should look out for free ones in the summer.
2San Francisco, CA
Living: San Francisco is straight up the most expensive city in the United States. Still, you'll get a little more for your buck than in New York. Living rooms and even yards are not out of reach for young professionals. And if you like nature, the cool thing about SF is that you can look out your window and see the city skyline and mountains at the same time. If you're thinking of living in SF, neighborhood is key. You can walk for 10 minutes and feel like you're in a completely different city.
Working: While you'll find a fairly balanced mix of professions in New York, San Francisco is heavily skewed toward the tech industry. If you're looking for user groups, you'll be in heaven. If you're looking for journalism conferences, not so much. Still, the entrepreneurial spirit of the city is infectious and can inspire people in any profession (and, at the same time, annoy the crap out of them). If you work remotely, San Francisco's got lots of quirky cafes to work from, though their concentration is very neighborhood-dependent.
Playing: In SF, I went to everything from a cat film festival to a queer poetry slam to a rock climbing excursion to a feminist book club. Meetup.com will be your best friend in this city. There are endless cultures and subcultures thriving there, and it's up to you to sift through them. Otherwise, there's still the chance of ending up in the same bar every Friday night.
Living: Some people consider Boston a more livable (albeit less lively) version of New York. Rent is far more reasonable, you can walk almost anywhere (down nice cobblestone streets), and the trains are full of peaceful, seated passengers. It's fairly easy to navigate and also very picturesque.
Working: The accessibility of workplaces will depend on where you're staying, but anything ending in the word "square" is a good bet. The Boston area is full of college students, especially in Cambridge and Somerville, so you'll feel right at home in cafes with your laptop.
Playing: Bostonians are more likely to be homebodies than party animals. Bars and clubs close early, and while my New York friends tend to go out every weekend night, my Boston friends often stay in for cooking or movie marathons. Drinking and dancing are always options, but you can't just wander aimlessly. You need to know where you're going, because parts of the city get really dead really quickly.
Living: I fell in love with Providence in college and still spend weeks at a time there. This quaint New England city is full of beautiful scenery, affordable housing (rooms for $500 per month are pretty easy to come by), quirky shops, restaurants, and people, and public events at the city's famous universities.
Working: For a fairly small city, it's really easy to find places to work in central areas like Thayer Street, Wickenden Street, and Federal Hill. In fact, one of my favorite things about Providence is the cafes. You'll find a few Starbucks, but you'll also find a lot of cute local coffee shops that serve home-baked goods and play indie music.
Playing: Providence is first and foremost a college town. There are plenty of places to get drinks at night, but clubbing, not so much. It's probably a more suitable place for a couple looking to get a dog and settle down than a single person looking to sow their wild oats.
Living: Somehow, despite Berlin's popularity among locals and expats alike, it'll look insanely cheap to anyone coming from a city like New York, SF, or Boston. You can legit get your own place for less than $500 a month. And don't worry: Pretty much everyone in central parts of Berlin knows English. Some people will even speak English to you by default. Getting around can be kind of confusing if you don't know German, but if you stay in the most popular neighborhoods, you can pretty much get by using one train system.
Working: Berlin is full of artists, entrepreneurs, and free spirits, so most nomads will feel right at home. It's also full of cafes filled with these kinds of people. If you're not sure where to go, many of them are concentrated in Mitte. My favorite, St. Oberholz, even lets you become a member so you can work from there at all hours of the day and night.
Playing: Americans, get ready for a culture shock. Berlin's clubs open around midnight, and people don't go out until even later. Germans party hard and save the next day for sleeping. Berlin is also famous for clubs like Berghain that are nearly impossible to get into. If you don't want to wait in line for an hour just to be sent home, opt for another one like Watergate or Suicide Circus. Or skip clubbing altogether and go to one of the many (earlier) performances or art shows around the city.
6Amsterdam, The Netherlands
Living: Amsterdam is one of the world's coolest-looking cities, with winding brick streets wrapping around endless canals. There are bike lanes everywhere and a huge park where you can watch ducks swimming and go to exercise classes. Rent is more comparable to big U.S. cities.
Working: In Amsterdam, you'll be charged with the task of figuring out what's actually a coffee shop and what's a, er... coffee shop. It's not always easy to tell the difference! Actual coffee shops with WiFi are not as common as one would hope, but when in doubt, look for a Bagels & Beans.
Playing: Obviously, Amsterdam is known for its coffee shops (the ones without WiFi), but many don't realize the fun nightlife the city has, which ranges from techno clubs to rock bars.
Living: Disclaimer: I went to Stockholm in the winter. Everyone I know who likes Stockholm was there in the summer. In the winter, though, it's a snowy mess with just a few hours of sunlight per day. But the trains are super nice! And the airport is hands down the best I've ever been to, between the upscale coffee and nicely decorated waiting areas. Seriously, you should arrange to have a layover there so you can see the city's best feature.
Working: The cafes are pretty nice here. You'll find Espresso Houses and Wayne's Coffees all over the place. They're really into matcha lattes and energy balls — though if you want a more cultural experience, look for a Swedish pastry shop. There's also no shortage of people doing interesting things in Stockholm. I found a bunch on Couchsurfing.com, which some people use just to meet people without staying over with them.
Playing: Stockholm's not as intense as Berlin, but they do follow the European model of partying where arriving at midnight is early. If you're looking for something to do at night, take a walk around Sodermalm.
Living: Hamburg is the second-biggest city in Germany and one of the most international, aside from Berlin (and maybe Frankfurt, which I'm leaving out because I found it really boring). People won't speak English to you by default, but if you speak English, they'll answer you. You'll find a lot of good food around Hamburg, from tapas to doner kebab, and lots of hookah bars. The canals also make it a romantic place to walk around, though it has the tendency to get cold and rainy.
Working: There are a number of coffee chains like Campus Suite and Coffee Fellows scattered around Hamburg, though they're sometimes a bit of a walk and the WiFi isn't always great. A lot of the people you'll find there are students — there aren't too many remote workers.
Playing: Hamburg is famous for its Reeperbahn, where you'll feel like you're at a party just by walking down the street. It's also the city's red light district. You'll find bars, nightclubs, shows, and shops scattered throughout. And if you can do it the European way and make it until 5 a.m., you can get breakfast at the famous Fish Market.
Living: I almost didn't include this one because I've only worked one full day here, but after that song, I thought you might be curious about it. The special thing about Ibiza is that everyone is there to lose their inhibitions, and you can get into a conversation with nearly anyone. Apartments and hotels are both pretty affordable, and you're surrounded by beautiful beaches.
Working: LOL. You don't really go to Ibiza to work, but obviously, there are people who live and work there year-round. If you get stressed out about work, your work will either become less stressful or totally ruin Ibiza for you. Either way, working from home will likely be literally working from home. There aren't many public working places.
Playing: You probably don't need me to tell you that Ibiza is the ultimate adult playground. Every night of the week between May and October, you can walk around Playa den Bossa, and people will be selling club tickets on every block. Gather information from all of them about which party is best that night before making your pick. Whatever you do, though, get the tickets in advance. You won't want to be stuck in line.
I realize it's a pretty random assortment of cities, but they're the ones I know best so far. If you happen to be thinking of going to any of them, hopefully you now know a bit more.