Urban Backpacking: 49 Tips for Long-Term City Travel

What I’ve learned traveling around many of the world’s great cities. These tips are reminders for me. If they apply to you, fantastic.

In May 2022, I graduated from New York University, and with it, said goodbye to a special chapter in my life. My lease in my beloved shoebox, 5th-floor walk-up apartment on the Lower East Side with creaky wood floors, and the one small window that turned into my fire escape-turned balcony also ended the same month. Instead of resigning and staying in New York, I set my sights on starting the next chapter with a new backdrop: Barcelona.

For those who know me, or follow me, you know that Barcelona holds a special place in my heart, and has since my first visit in 2017, when I was 18. Partially because of COVID, and partially because I was busy graduating from NYU in three years, I hadn’t been back since 2019.

That made my post-graduation plans obvious. Before making any other committal moves, I would go back to Barcelona, probably for a month or two, and get to know even better the gothic metropolis that’s a second home for me.

Well, my “month or two” in Barcelona turned into 90 days, the maximum stay allowed in the “Schengen Zone” in a 6-month period.

I didn’t just stay in Barcelona, either. I spent a week high-speed transiting around three cities in Italy, with a stop in Zurich, Switzerland. I took the train to Madrid for a week, to experience Spain’s storied capital, and I flew out to Bilbao in Spain’s Basque Country.

After my 90 days ended, I went to London for a week (outside of the Schengen Zone), before returning to the US.

When I got back, Instead of signing a lease, I decided to batch a flood of travel opportunities. I had a friend in Miami who had been inviting me for years, a marketing event upcoming in San Diego, a client in Orange County, California who I’d never met in person, and a work friend in San Francisco.

After California, My tour of US cities continued.

In total, over the last 5 months (and counting), I have been to the following cities (in chronological order):









New York (pit stop home)



San Diego

Oakland (and next-door Berkeley)

San Francisco


Vermont (not a city, but another pit stop home)




Three months of urban travel bled into four and five. Then it was nearly winter, and why would I sign a lease in New York that starts in December? It sounds like I would be urban traveling more. With more plans on the way (notably, back to Europe to see my beloved Spain, and then to Central and South America).


Future Plans

3-week break in New York (Specifically Brooklyn, since I wanted to give BK a tryout.)



Washington D.C.


Barcelona (hello, el meu amor)





Mexico City

San Salvador (where I have extended family)

(The Latin America leg of the travels are in flux.)

While I sought out specific experiences, one of the beauties of my travels is often what’s been unexpected. I’ve had experiences I hadn’t imagined, and therefore couldn’t have hoped to hope for.

I learned another language. I deepened friendships, made new ones, and had, however brief our mutual stint in the city may have been, passing interactions that I’ll cherish.

I’ve lived out a big part of what Personal Finance expert Ramit Sethi calls your “rich life.” For me, my rich life involves seeing my favorite bands no matter where in the world they’re playing or the day of the week. That means I was in Chicago for Knuckle Puck’s back-to-back hometown shows, in Austin to see A Day to Remember on my birthday, and Zurich, Switzerland to see Neck Deep on a last-minute whim.

And I’ve saved money.

I’ve had more time and space to work than I otherwise would have, and, since I wasn’t paying nearly $1800 in rent for a shoebox like I was before, I was saving more money.

Truly, I’ve been living the life. I’ve made it. Whatever happiness is, this is it. Stress is low. Fun is high. New experiences and constant learning is my everyday. Philosophical ponderings aside about what happiness and success are, all I know is I’ve never been happier. 

This is possible because I have prioritized my freedom and flexibility for this chapter of my life.

Through a lot of trial and error, too many flights, trains, and booking too many hostels and Airbnbs, I think I have something to share about how to save money, making urban traveling sustainable, and one of the most rewarding, enriching, unforgettable experiences of you’ll ever have.

Here are my tips for successful urban backpacking. I have organized these by category, but there’s often quite a bit of overlap.

But first…

Why Cities? Why Urban Backpacking

With cheap travel and packing light, people often think of traditional backpacking excursions, sleeping in tents and hiking.

I think a lot of this minimalism from traditional backpacking can carry over into urban travel. If you like cities, by thinking of it as backpacking, you can give yourself a ton of headaches, and thousands of dollars.

Here are some of the advantages to hopping from city to city with just a backpack.

You Don’t Need to Worry About Getting Things

Every city has all of your basics. Convenience stores are universal. No, you don’t need to pack a dozen razors or anything else you can easily buy. I even bought flip flops instead of bringing them, because they literally cost $7. Nor do you need to worry about hassles like rental cars, because cities have trains, trams, and buses to take you around, including to and from airports.

Cities Are as Stunning as Nature

Often, the two aren’t as separate as you think. In fact, New York exists precisely because its nature and location are so amazing. New York City, geographically and ecologically, is perfect (any extent to which it’s not, is because humans have messed with it, which is interesting to study in its own right).

Barcelona is another great port, the Spanish Empire’s gateway to the Mediterranean, with gorgeous beaches and phenomenal hikes interconnected by a metro, and just about anything you can want within a few hours.

To Study Cities is to Study How Humans Congregate 

I believe that if you want to study humans, human nature, and politics, you have to look at cities. 

To study and participate in cities, is to study how humans come together, why they come together in certain places, what they build (and what they don’t), what their values or and their culture is like.

Relatedly, if you want to interact with politics, this is where it happens. From transit, to social issues, to how people in different parts of the world think, cities are where you see it all played out in real life.

Cities are also where the action happens. From shows, to museums, to night life, cities have it all. As has happened in my life, I’ve gone to cities partially to seek out brilliant people, and you’ll find many of the world’s sharpest (and most differing) thinkers who call one great city or another their home.

Relatedly, Cities are where we meet so many people different from us

I love what Hostelling International says about travel, that, when people meet different people, and explore different cultures, we learn to accept, embrace, and love those who are different from us. This is one of the best things to help bring us together, while allowing our differences to flourish, in a polarized, often ‘us and them’ world.

49 Tips for Urban Backpacking

Packing and Clothing Tips

In my view, what separates “Urban Backpacking” from digital nomading is a fewfold.

The most obvious of these is that I did all of this with a backpack. I checked a bag to Barcelona, mostly to hold all of my books which I ultimately didn’t need because I ended up buying a ton. So if I were to do it again, I wouldn’t even check that bag.

During my Europe travels, my checked bag stayed in Barcelona. My first tip, then, is obvious…

1) Don’t Check a Bag

Checking bags is lame. Cool kids don’t check bags.

Less Travel Stress

You don’t need to worry about getting to the airport excessively early to deal with the bag drop-off lines. Nor do you need to worry about waiting for baggage claim when you land, or the horror stories of lost luggage.

It also makes travel from airports much easier. If all you have is a backpack and a briefcase, you can comfortably take transit from airports.

If you arrive at a train station, you can even take bike shares or scooters, which are in just about every major city, and only cost a few bucks. This is why I use a backpack and not a smaller suitcase or a duffel bag.

More flexibility with check in/check out

If you have a suitcase, it’s hard to do stuff before checking in and after checking out of your housing. When you travel light, it means you can book a 10pm flight, even though you have to check out at 11am, and still enjoy the day in your place.

Budget Airlines Jack Up Prices For Add-Ons

Budget airlines get a bad reputation, but in terms of getting you from point A to point B, and even the in-flight experience in economy, I’ve found the differences to be negligible. But the business model for them means anything extra costs a lot more.

If you want cheap flights leave the bags at home.

You’ll realize you don’t need that much stuff

I realized my stuff was a hindrance to my happiness, not an asset. I felt happier when I didn’t have anything (as long as I had clean socks and underwear.) If you think you need a ton of stuff, this is an opportunity to realize that you don’t.

The freedom of knowing I can pack up everything I have in 5 minutes means I could be completely open to any opportunity that comes my way.

To that, though, here’s how you can get the most out of your limited space.

2) Bring fewer clothes, and more socks and underwear.

Sure, there were times when I wish I had my green The Story So Far t-shirt for a certain concert. But way more often I’m glad I had more space in my backpack. As much as I wish I could have teleported my red checkered Vans for that one night out, it really didn’t matter at all.

In total, I had a backpack and a shoulder briefcase. The briefcase is easy to put under an airplane seat, and buys you some extra space without distracting much from comfort.

Here’s exactly what I included in each.

Total urban backpack list:

  • One pair of Levi’s jeans because they hold up and don’t really need to be washed.
  • One pair of joggers. Only if you’re going somewhere with cold weather.
  • Two pairs of wearing out shorts. Only one if you’re going somewhere with cold weather.
  • Two workout shorts. One with liners, one without.
  • Three t-shirts and one workout shirt. Make the t-shirts usable for workouts, if necessary. Make sure you have one band shirt for concerts.
  • Six underwear
  • Six pairs of socks. Only Darn Tough socks.
  • One of your two books: the one you’re not currently reading. Usually for me this is a book I’m currently writing about. You will buy books when you’re there. You know this about yourself, so resist the temptation to pack more books.
  • Going out shoes that you can comfortably walk around in forever, like Vans, Converse, or Stan Smiths. They can double as workout shoes if necessary. I also carry sneakers, and tie them to the strap on my Burton backpack. This is one of the nice features of my Burton backpack, since they’re made for skate kids, they have two big sturdy straps designed for holding a skateboard.
I’ve had it since literally 2010. This Burton backpack is a 6th grader. Its zipper lasts no matter how much you stuff it. Super high quality. Perfect for strapping things to it.
  • Travel pillow. This stays attached to my backpack.
  • Toiletries. Toothbrush, travel toothpaste, travel deodorant, travel shaving cream, electric toothbrush, floss.
  • A lock. Keep one key on a keychain with your airpods, and the other in your backpack, unless it’s a combo lock. This is crucial for hostels and random gyms.


All of this fits comfortably in my Burton backpack. I’ve brought more in the past, and always regretted it. 

Total briefcase list

  • Laptop + chargers
  • Airpods
  • Journal
  • Writing Journal
  • Small commonplace book (languages, quotes, etc).
  • The one book you’re currently reading. (Since you’re not bringing more than two books total.)
  • Two highlighters, two notebook pens, and two book pens. (the book pens, for me, have much finer tips so I can write in margins. Again, this is a very David thing.)
  • Passport + wallet (duh.)

3) Leave Extra Space In Your Backpack

You’ll want to leave empty space in your bag. 

I made the mistake of squeezing all I could into my backpack. “Oh, I have space for my red Birks! Amazing,” turned into dread when I had to repack everything at every destination, and had to repack it every time I took something out.

If your backpack is stuffed to the point where you can barely close it, it’s also going to be much less comfortable to bike or walk for a long time in.

If you leave space you can also buy small things, like a few books.

4) Do laundry whenever you have the chance.

If possible, do it each time the day before you head to a new place, not the day of. That’s asking for a wet clothes disaster because of a fucked up dryer in the Airbnb. And since you packed light, your laundry load will be light.

5) Leave things in your Favorite/frequent cities

This is a unique situation, but thanks to my Spanish family, I have everything I need to live in Barcelona. I left some books there as well.

Work/Productivity Tips

For me, urban backpacking has not been a vacation from work. In fact, I have been working full-time, and other than from when I was 18-20 absolutely grinding as a personal trainer, I’ve been working as much as at any other point in my life.

This brings me to the first and most important tip.

1) Work a Virtual, Flexible Job.

The best way to save money traveling is to make a lot of money while you travel. Every single month since May, I have made progressively more money.

Until a few years ago, the idea of virtual work and traveling while working was only available for specific jobs and for a select few, the business owners and semi-retired.

(The exception here is those who took Tim Ferriss’s advice back in 2007, when he suggested “mini-retirements” in The 4-Hour Workweek.)

With the rise of virtual work and big changes in how we think about the typical work-industrial complex, there are more and more options to work while traveling.

I work for myself, which has made it even easier. As a freelance writer, I take on projects I want, do them when I want to, and set expectations with clients that work for me.

Concurrently with this, I have some passive income coming in from a project that I have equity in, which I explain in this article on how 3 articles make me $1000 a month.

If you don’t have a job with flexibility, and you want to travel, I suggest finding one. There are so many ways to make money today with a laptop, wifi, and a generally well-functioning brain. The latter of these may be the hardest to find, but if you have one of those, then start learning skills that you can use to work on your own, from your laptop.

My friend Jess Anders teaches people how to start their freelance writing careers, for example.

If you think you need to make a ton of money to travel, you’re probably wrong, especially if you’re used to living in a place like New York, as I was.

I spent much less traveling the world because I didn’t have the fixed expenses that ordinary life requires. Namely, I wasn’t paying rent. I enjoyed 3-course meals, drinks, and a nice Airbnb here and there, and I still spent less money. I routinely bought all of my friends’ food and drinks too.

As you’ll see from other tips, getting flights and housing can be relatively inexpensive. If you spend $1000 to get to and from Europe, you’re bad at booking flights.

“Can’t afford to travel,” is often ridiculous. If you’re a financially independent person living in the United States, then you can afford to travel.

How can you not afford to travel, honestly. There are tons of amazing cities that are much cheaper than even mid-tier US cities. Seville, Spain, Bologna, Italy, and Bogotá, Colombia, are all cheaper than fucking Colombus, Ohio.

At the risk of letting this article turn into unsolicited career advice, I’m going to assume you work a virtual job.

2) Work for 3-5 hours a day

In 1955, author Cyril Northcote Parkinson coined the now famous “Parkinson’s Law,” which is the idea that work expands to fill the time allotted for its completion. When I work all day, I often don’t get much done, and rarely more done than if I’d concentrated my work session. Working all day also rots my brain.

Paradoxically, when I was always in a place that I wanted to explore, I got more done. I found a good rhythm by blocking off half-days for work.

I got the same amount of work done in 2-3 hours as I would have in 8-10.

It’s time to throw out preconceptions about how much “time” you need to spend working. Time is not the currency of great work, especially creative work.

Instead, I would set aside “half-days.”

Often it was in the morning, say, from 9am until lunch. Sometimes I split it up into two sessions. I set my to-do list and worked until it was finished. I took breaks for food when I needed to. I hardly ever work typically “work days,” and when I’ve tried to, I don’t actually get more done.

Even more importantly, though, keeping these “half-day” guidelines made sure I was, well, living.

There are a plethora of quotes from writers about the importance of living life. Henry Miller said, “Keep human. See people. Go places.” Ryan Holiday said, “Writers lead interesting lives.” 

The half-day rule ensured that I was doing that. 

Quote from the American Writers Museum in Chicago (a fantastic hidden gem I found during my week in the Windy City)

Half-Days Keep My Mind On The Challenges It Should Be Focused On

In Paul Graham’s essay, The Top Idea in Your Mind, he discusses how most of us have, at any given time, one big idea that we’re thinking about when our mind wanders. As a writer, this is usually the given essay that I’m working on.

If we’re not careful, though, it can become an undesirable idea. In Graham’s case, an entrepreneur, sometimes getting funding dominated his brain, when it should have been on the actual business. He writes, “The problem is not the actual time it takes to meet with investors. The problem is that once you start raising money, raising money becomes the top idea in your mind. That becomes what you think about when you take a shower in the morning. And that means other questions aren’t.”

This is also the problem with working too much and not living enough. When I work too often, my mind gets muddled by supplement headlines and content articles, when it should be on the ideas that inspire me.

By keeping my work to half the day, I made sure I had the space for the ideas that should be on the top of my mind to hang on to a majority of my day. 

If it weren’t for this rule, essays like how I rediscovered my creative soul and learning an endangered language, simply, I wouldn’t have written.

I didn’t work every day. Obviously, I took days off. But if I wasn’t doing anything in particular on a certain day, like away for the weekend with friends, then I mailed in a half day. Generally I worked on weekends, and honestly, couldn’t care less. I loved the routine of working a few hours a day.

3) Charge Your Laptop When You Have The Opportunity

If it’s convenient, plug it in. A low battery is not a stress you need in your life.

Relatedly, remember that other countries have different types of chargers. I use the same USB charger for my Mac and iPhone, so when I got to Barcelona, I went right to the Mac store to buy the adaptor, which easily swaps out for the US one.

I did the same for the UK. Just have a plan to get your charging situation in order. Airports also sell all of this stuff.

4) Keep Something Loaded Offline on Google Docs

Spotty wifi ruining your work session is also a stress you don’t need in your life. I keep a separate chrome tab open that has something I can work on offline, as well as all the research for it loaded up.

This is especially clutch for flying. I never buy wifi on flights. Instead, I do work offline.

5) It’s Okay to Go to Touristy Coffee Shops

While I generally have an aversion to overly touristy plans, as I think it keeps you from seeing the real soul of a place, sometimes you need reliable wifi, outlets, and a place where they don’t care if you’re there for 5 hours.

Lots of times cities have chains that you can rely on. I recommend looking this up when you get there. For example, Barcelona has Sandwichez, Madrid has Vivari, and almost everywhere has Starbucks, as a last resort.

Of course, you should also explore other coffee shops, but at these ones, get coffee or a pastry, and enjoy it. 

I love to write by hand in these situations. Many of them don’t have wifi and discourage computer use, like this coffee shop in Bologna.

Translation from Italian: We don’t have wi-fi… Talk to each other.

6) Use Caffeine as a Tool

I love using caffeine in a few circumstances:

  • To reset your circadian rhythm. After red-eye flights, I drink coffee when I land in the morning
  • When you’ve gone out but need your half-day of work
  • When you’re walking around a city and want to be super attentive. These caffeine highs are amazing. I drank 3 cups of coffee in Italy one day and made me feel like I was on fucking MDMA. Caffeine can be a tool for fun, also.

7) Go to Cities With a Work Component

You can write it all off on your taxes. I will write off my Orange County and San Diego trip expenses.

Lifestyle Tips

This, obviously, could be its own article. In many aspects it already is, like this article on how I learned Catalan in 3 months.

Instead, these are a few general lifestyle/culture pieces of advice.

1) “Enter The Spirit”

In The Art of Seduction, Robert Greene has a chapter called “Enter The Spirit.” In it, he shares the story of the American actress and dancer Josephine Baker and what led to her success in Paris after moving there in 1925. “Baker sensed that their interest in her would quickly pass to someone else. To seduce them for good, she entered their spirit.” Greene continues, “She learned French and began to sing in it. She started dressing and acting as a stylish French lady.”

When we enter the spirit of wherever we are, we open ourselves up to new customs, ideas, and ways of life. In turn, this means we can build deeper relationships with the people, and further understand the culture. 

This can take on an array of practical applications.

Learn Their Language

I’m obsessed with language learning, as languages are the portal to a culture. For all the reasons I think it’s important, again, check out this essay.

Aside from it being one of the richest experiences you’ll ever go through, just learning a few words of the language where you are will earn you respect and friendliness from the locals. They’ll see you as somebody just trying to enter their spirit, and when it comes to making friends and getting friendly looks, that goes a long way.

Learn the basics: Hello, good-bye, thank you, do you speak English.

You can’t understand a culture, truly, until you start to learn the language.

Eat their food.

The food near the big touristy attractions will be, well, touristy. And overpriced. Go to the bars and restaurants the locals go to and attempt to order the way they would order.

Look up what the classic food options are for locals, and stray away from the well-walked tourist paths.

Take public transit.

On public transit, you’ll see the wide array of people in the city, especially, in my experience, on buses. That’s where you’ll see people living their everyday life, having their everyday experiences. You might even have them strike up a conversation with you, as happened to me in Barcelona, and which I wrote about for one of my newsletters.

Ask questions about politics and policy.

Since it’s not your world, you will see how politics have shaped the whole existence of the city. Why are there train lines here or there, or neighborhoods with different textures, or certain laws around any number of topics?

Often, this evolves into deeper historical discussions. In Barcelona, for example, mundane observations about the interplay between Spanish and Catalan quickly turn into political discussions dating back hundreds of years.

Everything that is our life, though we don’t realize it, has been built on political decisions. Asking about what it is that shaped their home, will give you uncommon insight for an outsider. (And, it’ll likely make you think more about where you’re from, why you speak a certain language, take a train or car to work, or have xyz values. It’s all entrenched in politics.)

2) Choose Depth Over Breadth

When I went to the Reina Sofia museum in Madrid, I wound up making my way up where Pablo Picasso’s famous painting Guernica towered over an entire room.

I knew the basic history of the Guernica, since I’d already begun my study of the Spanish Civil War. Picasso made it in response to the bombing of the ancient Basque capital by Nazi German planes.

I was absolutely stunned by the enormity of the piece and all of the numerous details, as well as the important historical context.

Although there was so much I wanted to see in that museum, I instead decided to sit and spend a few hours with Picasso’s masterpiece. The museum closed on me, and I still wish I had more time. So much of the painting is a mystery to me, and when I go back to Madrid, I’ll spend even more time with Guernica.

During my 90 days in the European Union, I obviously had the itch to see more, to explore more. I still haven’t gone to Paris, or Venice, or a number of bucket list places. Often, I simply chose to stay in Barcelona. In fact, some weeks, I didn’t even leave the borders of Gràcia, the Catalan neighborhood where I stayed.

My growing connection with Barcelona has been the most rewarding component of my travel experiences. Breadth and exploration is wonderful, but it’s okay to ‘miss out’ if it means you can go deep, whether that’s with a piece of art at a museum, a language, a neighborhood, or more.

3) Don’t Feel Obligated to See The Touristy Stuff, Or Obligated to Do Anything, Really

One of my favorite words in Spain Spanish is guiri, which is a disparaging word for tourists.

The decoration at Gracia’s Festa Major made me laugh the most. For context on this, check out this short writing piece of my experience with the Festa Major.

During the summer, we joke that there are two Barcelonas. One is the migration pattern of tourists from Barceloneta Beach, to Sagrada Familia and Parc Guell, to the Bunkers, and back to the nightclubs.

You can go and do all of that, but that’s not what the real Barcelona is. In fact, we all actively avoid those areas, because they’re suffocating and there’s a decent chance you’ll get your phone stolen.

You could also not do any of that, if you don’t want to. When I go to cities, I try to see bookstores and parks, and restaurants and places that people who live there go to on a regular basis.

There are reasons, though, why some tourist attractions are tourist attractions. Central Park truly is a marvel, as is the Sagrada Familia.

In general, then, if you want to see a tourist attraction, absolutely go for it. Do the thing. Get the overpriced ticket. But do not feel obligated to. 

4) Learn to Love Doing Things Alone

Traveling alone means you’re going to eat at restaurants alone, go to concerts, museums, or parties alone, and spend a lot of time with just your thoughts.

That means you have to enjoy, or at least put up with, spending time with yourself.

The initial social awkwardness and the “wow, you came to this concert alone!” remarks from strangers will be the least of your worries.

When you eat dinner by yourself, will you feel the obsessive need to take out your phone to avoid sitting with just you and your brain? I know I did.

Over time, I grew to love this time alone. I even found myself going out of my way for it. When I’m alone with my brain (and maybe a 3-course meal in Europe), I often find myself with my best ideas for essays or life. It’s also when I tend to read the most (which I’ve learned also corresponds with my happiness).

Socially, I now share no awkwardness eating alone, or going to parties alone and letting the social scene come to me. If you do want to travel alone, but also want an easier invitation to be social, we’ll talk about hostels later.

5) Take Your AirPods Out. At Least Just One.

Your AirPods are your world. Your music, your podcasts, your audiobooks. When traveling, get out of that world. Listen to the languages in the streets, the conversations, and the sounds of the city.

Housing Tips

Housing, almost more than anything, can make or break a trip. A shitty living situation will make the best cities in the world seem terrible.

Financially, along with flights, they are going to be your biggest expense. Of course, typically hotels can cost hundreds per night, while hostels cost tens, and the couch at your friend’s place in Miami is, well, free.

1) Don’t Have a Lease 

I spent less money traveling than I would have living in a place like a normal human because I didn’t have rent to pay. Since I got used to New York rent, I had a decent-sized budget I could now spend on housing, flights, food, and other shenanigans. 

If you’re savvy with your housing, this is how you make traveling cheaper than regular existence.

2) You Don’t Need Perfect Sleeping Conditions

Whether you’re on a friend’s couch, a hostel, or a stranger’s bed (Airbnb), some silicone earplugs and an eye mask will help you adjust to sleeping in less-than-ideal environments.

Instead of an eye mask, sometimes I just wear a beanie at night and put it over my eyes. (This is a great tip for flights where you’re trying to sleep as well.)

If you’re worried about sleeping on bunk beds, quit being a little bitch. It’s fine. You’ll be fine. In general, I love that I now know I can sleep just about anywhere, in any reasonable condition.

The Roman and stoic philosopher Seneca said, “Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: ‘Is this the condition that I feared?’” (Letters from a Stoic)

Often this is what we fear. And yet, when you’re in a situation like sleeping on a bunk bed, you realize how little you need to be happy. Or, at least, I did.

3) Choose Places Based on Where You Have Friends (and therefore, a couch)

As I mentioned, I’ve had friends who’ve been inviting me to visit their city and crash with them for years. That’s how I ended up in Miami, where I crashed with my friend Brett. This is a decent starting place for choosing places to go, and of course, housing in these places is free.

You don’t want to abuse this. So I have a few guidelines for crashing with friends. 

1) Have They Invited Me?

Obviously, only go if you’ve been invited. I don’t usually ask to crash, unless it’s that type of friendship.

2) Would I Be Excited for Them to Crash on My Couch?

I’ve hosted lots of friends on my couch, and it has been some of the most fun I’ve ever had. Often, I look forward to it. If I’d be excited for them to stay with me, that means they’re probably excited for me to crash with them. It also means, when they’re in New York, I’ll be excited when they ask if they can crash at mine.

4) Hostels Are Like the 1st Week of College

While I have friends in lots of places, they don’t cover the whole world. For places where you want to be social and meet people, and travel for super cheap, you can’t beat hostels. 

They’re like the first week of college, without the classes or the RAs.

The social scene is often an absolute jungle, and you’ll meet people from all over the world. In London, I learned a lot more about Australia and the Netherlands than I would have expected. It led to some of my most fun, and growth-inspiring, travel experiences, all for around $30 a night.

(In places like Colombia, they’re often less than $15 a night.)

Even in expensive cities, hostels rarely cost more than $35 a night. While the social hostel scene in Europe is generally much better, big North American cities have decent hostels.I had amazing hostel experiences in San Francisco and Montreal. They were less social than the Europe ones, but I still connected with other people.

For US hostels, I’d look for ones that are part of Hostelling International, because all have a certain standard that you know will be adequate.

Yes, they’re safe and secure. You can easily lock your valuables up, so bring a lock with you on your travels.

One of the downsides of hostels is that if you want to immerse in the culture of where you’re in, you probably won’t find it in a hostel. I heard more France French than Quebecois in my Montreal hostel. Hell, I heard more Dominican Spanish in my Montreal hostel than Quebecois.

In Spain, I’ve never stayed in a hostel. The last thing I want to do in Madrid is meet someone from Chicago or Dublin. This brings me to the next option.

5) Stay in Shared Airbnbs for Targeted Language Learning + Culture Immersion

While hostels are fun, inexpensive, and great for meeting new people, they’re international hubs, and therefore not the best for language or cultural immersion. When I went to Italy, I stayed in an Airbnb in a two bedroom apartment with a gay man from Bologna and his three cats. Francesco had chic, varied earrings, fun pants, and offered me a beer every night.

We sat on his couch, speaking in his rapidly improving English. We discussed Italian politics, how Italy doesn’t have a two-party system, but it’s still fucked up, the differences between northern and southern Italian accents. I learned a lot more about Italian culture, observed how a local lived, and got great recommendations on what locals do.

If I want to learn Italian in future, I would replicate this. I wouldn’t stay in hostels in Italy, I would stay in people’s homes with Airbnb.

Since it’s a shared place, they’re usually inexpensive. This Airbnb was about $40 per night, and it was nicely located.

6) Plan a Night or Two NOT in a Hostel

Hostel life, for me, reached a point after five nights in a row where I craved a day where I didn’t have to introduce myself to anybody. For every 5 nights in hostels, I like 1 or 2 nights in a place with a friend, or in an Airbnb.

7) Write Great Airbnb and Hostel Reviews

How you do anything, is how you do everything. While this borders on the cliché, I also think about this in the context of writing. That is, how you write anything is how you write everything. 

Whether it’s a text, an important essay, or an Airbnb review, treat it like real writing. Watch your punctuation, reread it before sending, and spend a few seconds thinking of the right word or the right turn of phrase.

As an example, here’s my review for my Airbnb host in Zurich.

The apartment was beautiful, extremely clean, and had an aura of calmness to it that made me feel right at home. Irina also exuded that aura of calmness to her that made me feel right at home. It’s in a quiet neighborhood that’s still close to the center so you have everything nearby.

Transit and Travel Tips

I’ve taken trains in US cities where most people wouldn’t imagine it, buses across international borders, and made intercontinental travel inexpensive.

1) Where possible (and it’s almost always possible), use public transit

When I first moved to New York, I felt (like a lot of implant New Yorkers) overwhelmed. Then I learned how to use the Subway, and the infinite vastness of one of the world’s great metropolises opened up to me. Now I even know New York’s buses very well, and my ease of getting around is part of what makes the place feel so comfortable, feel so much like home.

The same goes for anywhere I travel. Taking a bus in Oakland made me realize I could get around Oakland, as did taking a Santander Cycle in London, or the metro in Madrid.

You will save money, yes, but you’ll also see the people who live there, the middle class, those just living their lives. If you want to get to know a place and its culture, take its transit. Books have been written about what goes on in the NYC subway, just from a cultural perspective. 

Other cities are equally rich in what their transit shows about their city. Taking Ubers, I view, is opting out of the experience of the city. Even if it’s a shitty public transit experience, that’s an important element to any city. You’ll learn which cities are made for humans, and which ones are made for cars. Orange County and Austin suck. Objectively bad places to live if you’re not rich enough to have a car.

Even in these places though, I like Austin much better now that I’ve figured out the buses.

I’m also a believer that a big climate solution is to just GET RID OF CARS, and this means investing in better transit, which begins by supporting it.

2) Get to airports early

Why the fuck are you gonna add extra stress like that? No reason for it.

Relatedly, don’t be in a rush in general. While traveling, I truly never have to be anywhere at anytime. The world literally will not be affected whether I’m at a certain place at a certain time. I will never look at stress or the imperial-capitalist concept of time the same again.

3) Watch out for airlines where you only get an underseat bag.

Look it up ahead of time, and either pack appropriately, or buy the overhead carry-on. In Bilbao I saw this and left more stuff in Barcelona. More often, I just made sure my ticket had the overhead carry-on.

4) Get TSA Pre-Check.

It’s a few bucks and it lasts 5 years, and reduces airport stress.

5) Get an Airline Credit Card

Whichever airline you use the most. I’ve had a JetBlue card for years, because they have the best New York → Vermont and New York → Austin flights.

I try to use it for everything, and many of my domestic flights have been free. They’re also great for Latin America. I still have enough points for more free flights, which is why I will probably keep traveling.

6) Red-eyes are cheaper and save a night of housing.

You mean I can get from San Francisco to Montreal for less than $200, and don’t need to figure out housing for a night, or lose a day to travel? Easy.

Yes, you won’t sleep the best, but that’s where caffeine as a tool can come in.

A cup of coffee after a red eye, and an afternoon nap, for me, ensure I have a normal day wherever I land.

7) Be Flexible With Your Dates

Browse SkyScanner for the cheapest flights to anywhere. If you’re flexible with dates and cities, you can get almost anywhere cheap. Be flexible with your dates. Problem solved. You’ll never by an overpriced flight again.

8) Layovers in London are the cheapest way to and from Europe. 

From London, you can find cheap flights (less than $100) pretty much wherever you want in Europe. I had a great experience with the new Norwegian airline, Norse Airways, getting from London to New York. 

London is a fun city for a 1-5 day layover. And, since it’s not part of the Schengen Zone now, it doesn’t run up your 90 day Schengen Zone clock.

9) Don’t be in London when the Queen dies.

All the fun stuff will get canceled. On the other hand, seize the historical moment. Head to Buckingham Palace to “pay respects.”

10) Plan around certain events.

Knowing I have a thing to go to in a place is weirdly grounding. For me, it’s usually a concert. 

I used Knuckle Puck playing back-to-back nights as the perfect excuse to go to Chicago. It also eases the potential overwhelm of long-term travel to have something, anything, on the calendar.

11) Watch out for Sunk Cost Fallacy when planning/changing plans.

I planned my week in Italy around two events: a concert in Bologna, and, three days later, a concert in Milan.

Unexpectedly, after I was in Bologna, the concert in Milan got canceled. I had already paid for my flight from Milan to Barcelona and my Airbnb in Milan.

But, without a concert, I didn’t want to spend so many days in Milan. I saw that the same day as the Milan concert was supposed to be, Neck Deep was playing in Zurich, Switzerland.

It was only a three and half hour train ride from Milan. In the back of my head, I felt my self-talk go, “but you already paid for your flight and Airbnb, and can’t get that money back.” But, that’s a psychological phenomenon called sunk cost fallacy.

The money was spent. I had the choice of spending more to see another amazing city and see another one of my favorite bands, or succumb to sunk-cost fallacy.

I bought tickets to Neck Deep, an Airbnb in Zurich for one night, a train ticket from Milan, and a flight from Zurich to Barcelona. I cut my Milan trip short, and went to Zurich.

Zurich was one of the highlights of my Europe travels, and of course, there’s nowhere else I would have wanted to be than the Neck Deep show.

Your plans will change, unexpectedly. You’ll have to choose between “wasting” money, and having the experience you want to.

You’ll eat costs on flights and housing. This, if you’re flexible and open to last-minute adventures, is part of urban backpacking.

Fitness/Health/Nutrition Tips

You know, for someone who’s been in the fitness industry since age 18, I have surprisingly little to say about this

 As a guy in his mid-20s, I have the privilege of good hormones that can make up for subpar behaviors, and since I have a great base of health, I can coast on a lot of good habits.

Nonetheless, this is how I’ve thought about fitness, and I’ve basically been able to maintain my athleticism and body composition, and most importantly, I feel good.

1) Go to Gyms When it’s Available, But Don’t Stress When You Can’t

Sometimes where I stay will have a gym, like a friend’s building, or a hotel fitness center, or a friend with guest passes to their gym. When available, I would get in a string of good workouts.

Then another place, like a hostel, wouldn’t have a gym, so I had no access to weights.

My program, then, ended up looking like 3 days on, 3 days off, depending on where I was, rather than a cohesive program.

Because the program was erratic, every workout I would do full body, and hit major movements:

  • Lower body push (a split squat or lunge of some kind)
  • Lower body pull (a deadlift of some kind)
  • Upper body push
  • Upper body pull
  • Hip Mobility ← This is just something I know I have to do, thanks to 18 years of playing competitive hockey.
  • Core
  • Cardio

If a gym had a fan bike, I took advantage and did bike sprints. I just used whatever I had at my disposal, and made sure I was checking major boxes.

2) Do Some Sprints In The Morning

Regardless of the gym situation, I try to get up and go outside every day. Andrew Huberman has ingrained in my head the importance of early sunlight and movement, and getting outside and doing a few sprints in the streets set a great tone for the day.

In hilly cities like San Francisco and Barcelona I could do hill sprints, which was even better.

3) Have a Smoothie or Protein Shake for Breakfast

I have had a smoothie for breakfast most days since I was 14. It helps me get in my protein, some fruit, and holds me over until lunchtime. Lots of times hostels have blenders and a fridge, so I just had to buy a few bananas, a bag of frozen berries, peanut butter, and yogurt if I didn’t have protein powder available.

That’ll cover several meals for a few bucks. When I couldn’t make a smoothie, I went to the nearest convenience store and bought pre-made protein or meal replacement shakes, one per each morning wherever I was. 

This means I only bought two real meals per day. This is a good way to save money on food.

4) Always Have Almonds With You

Okay, it doesn’t have to be almonds. But I love almonds. I always buy a big bag, which places like CVS have, and then when I run out I go buy another one. Almonds are my ideal snack.

5) Look Up Popular, Cheap, Moderately Healthy Food in Any Place

Think about the equivalent of a bodega in New York. In Spain, bocadillo spots are key because you know you can get good cheap food pretty much anywhere.

In SoCal, I knew my taco spots.

The places where I figured this out, I had much better food experiences and wasn’t wasting a ton of time looking for food. 

It also kept me from spending a fortune on meals.

6) Never Stress About It

Because of these rules, I never had to worry about being too unhealthy. That way when dessert included the crema catalana, I could eat it guilt-free.

More Tips

I didn’t know what category to put these in.

1) Travel Around Your Home Country

The United States is a vast, mind-blowing country with almost everything to offer. While there’s an excitement to traveling abroad, your home country has so much magic you haven’t seen. Miami felt like a Latin American center, and I spoke more Spanish than English. I came to see that Chicago and San Francisco in their own right are fantastic cities.

I also got a better perspective on how the city experience in the US doesn’t compare to Europe, and where it does.

2) Be a Tourist in Your Own City When You Get Back

I remember when I went to Bilbao, Spain, the largest city in the Basque Country region, I was struck by the Guggenheim museum at the centerpiece of a gorgeous city. Out in front was the famous American art piece, puppy, and inside, a range of art from modern Basque artists to Andy Warhol.

It was one of my favorite museums I saw in Europe, and, even though I’ve lived in New York for three years, I’ve never been to the original Guggenheim just a few blocks from the MET on the Upper East Side.

I realized how little I’ve explored of my own city, and will make it a point to map out excursions to different places and neighborhoods.

Traveling the world has shown me that the world is full of beautiful places, while also showing me how special my home city is. After traveling, I love New York even more.

3) Keep Your Phone in a Reliable Pocket

Some cities are worse than others, but pocket theft is common throughout the world, even in relatively safe, modernized cities, especially in touristy areas.

Make sure your phone is safe.

I like to use a phone wallet, that way I only have to worry about one thing. I also keep at least a credit card where I’m sleeping, though, that way, if I lose my phone, I can still buy stuff and I’m not totally fucked.

Mitigate big risks with simple solutions.

Taking this a step further, I’ve bought a few t-shirts with zippered pockets made for a phone and passport. They’re plain, simple t-shirts, and take this stress out of going out. 

You can check them out here at Clever Travel Companion.

4) Keep Track of Everything With a Spreadsheet

Now, I don’t consider myself a type-A person. But, I started to lose track of which dates I was going where, whether I’d bought my flight, booked housing, or tickets for whatever event.

I put it all in a spreadsheet, and it made everything much easier to keep track of.

Here’s what a snippet looks like, so you can see it.

9/5-9/10LondonHostel11:00 Vueling BCN –> LGWMurder the Queen
9/10-9/14New YorkZaf and Jorne1:10 Norse LGW –> JFK
9/14-9/17MiamiBrett9:50 JetBlue JFK –> MIAHang with Brett
9/17-9/26AnaheimTP12:00 American MIA –> SNAWork at Kaged HQ
9/26-9/30San DiegoAirbnb w/Brett8:55am Greyhound Anaheim –> San DiegoTraffic and Conversions marketing event

5) Don’t Plan Your City Itineraries

Yes, it’s important to plan some stuff. But, when traveling long-term, it’s easy to get caught up in where you’re going next. 

It’s even easier to waste hours of your day researching a city and things to do. I hate doing this, because it distracts me from where I am and doing stuff.

In this respect, long-term travel is like meditation. You almost have to stay focused on the present, and it’s easy to catch yourself drifting too much into dreamland (or stress land) about where you’re going and staying, and when and how you’re getting there. As a rule, then, I don’t really plan for a place until I’m there.

Sure, I’ll buy tickets for events,and book housing, but I’m not looking up much on Google maps, or checking museum hours a week ahead of time.

6) If You Still Have the Itch, Keep Traveling

Initially, my plan was to more or less fuck off in Barcelona for a month or two as a gift to myself for graduating, then find a new apartment in New York.

But I came to love the freedom of traveling.

I didn’t want to leave Spain, and I wanted to see more, go to more places, and take advantage of this period in my life. Two months planned turned into three (up until the last day of the travel visa) which turned into, ‘what about the US?’ which turned into ‘wait I can go back to Europe, why am I just gonna sit here in the northeast during the winter?’ And that’s how I ended up traveling for going on six months, with several more months planned. At least, that’s how it went for me.

You don’t have to commit to months. You can take it a few weeks at a time, and continue to reevaluate. But if you’re still excited to travel and explore, and you have the situation to do so, keep doing it.

Eventually, I know I’ll want an apartment, with all my books and the stability of familiar surroundings and routines. But, the itch to travel still outweighs that.

7) Write

Writing is reflecting, which is learning. If you want to make sense of the whirlwind of things you’re thinking about, write about it.

8) Pause to Reflect on How Sweet Your Life Is

As I’ve traveled, countless people have told me, “That’s amazing, keep living it up,” or, “What a year to be David.”

I’ve had moments where I’ve stopped I’ve paused to reflect on how sweet my life is.

You’ve built this and made it happen, I tell myself. So many people dream of long-term travel, or working from their laptop like you do, of travel and financial freedom, and you’ve set up your life so that traveling is cheaper than regular living.

This is your life, or at least, a special chapter in it, which, once it’s over, you’ll know how great you had it. You’ve made it. The time is now. Soak it in.

“These are the times,” as my dear friend Kelly Butts-Spirito says.

Sit on a bench in a random city with perfect weather and think about how the fuck you got to this bench in this random park in the random city. The answer is: you. You’re in charge of your life.


Have questions about urban backpacking or long-term travel? Or some great tips that I could use? Lately, I love talking about this, so please hit me up on Instagram.

One thought on “Urban Backpacking: 49 Tips for Long-Term City Travel

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s