How to Start Traveling Indefinitely — Break Away, Logistics, and Sustaining the Lifestyle

Whether you're eighteen or eighty, the idea of setting off on an epic traveling adventure may be something you've thought about. Maybe a lot.

I was twenty-two years old when I hit the road in 2007. Within weeks I was in love with the lifestyle. Within months it addicted me. Once a full year went by, I knew I could sustain this life of travel indefinitely.

Now, in my fourteenth year of living on-the-go, I've been fortunate enough to inspire others to do the same — which is what I hope to do in this post as well. I've answered the questions and seen the real (and made-up) barriers separating a stagnant life from a unique journey.

Perhaps you have some of these questions and barriers as well, or maybe the logistics of travel are unknown and daunting. Maybe you're wondering how the money is going to work out. To know how to start traveling, let's think about it in these stages:

  1. Consider your travel rhythm and style
  2. Breaking away
  3. Travel logistics
  4. Sustaining a life of travel

1) Consider your travel rhythm and style

This can be the rhythm of your life, not an interruption. There are plenty of travel rhythms that might fit your vibe.

  • Travel non-stop and indefinitely, pausing in places for just a few days or weeks at a time before moving on (this has mostly been my style).
  • Travel for six to nine months until you get weary, then rent a place somewhere fun and productive for six to nine months, get stir-crazy, then hit the road again. Rinse and repeat.
  • Take a year-long-trip every two or three years.
  • At the very least, hit the road for a few months at a time whenever you can.

The era of limited societal norms has passed. Except for some extreme circumstances, you can lead yourself through whatever adventure you choose, and chances are there are people doing something similar with examples to follow. You're free to be unique without being alone.

Like your rhythm, your travel style may adapt as you go. This will depend on your interests, comfort level, and finances. I'm talking about things like:

  • Transport: Walk, hitchhike, bike, drive (car, van, RV), sail, buses, trains, flights.
  • Accommodation: Camp, stealth camp, hospitality networks, Airbnb, hostels, hotels
  • Activity: Hiking, zip lines, museums, breweries, projects, adventure tours
  • Food: Street food, bread and cheese from the grocery store, fast food, fine dining
  • Funding: Bankroll, incorporate income into your travel flow, intermittent pauses to earn cash

I'll cover some of these factors in-depth in the travel logistics section. Your ideas now may change with the more you learn, and even more so once you're out there living.

For example, you may find that using free hospitality networks is more gratifying than staying in hotels, or hitchhiking (free as well) is more fulfilling than riding the bus. Or more convenient.

Money affords options, but that's trivial when the best option is free.

On the flip-side, you might become inspired by top-notch restaraunts and find yourself in need of a little more cash to support the habit. Then again, you might find that your blog or videos reviewing said restaurants catch fire. Or you score a gig in the kitchen for a few weeks during the busy season in some badass beach town. Suddenly you're getting paid to chow down that highfalutin sustenance.

There're plenty of ways to make money and plenty of ways to live without it. Anything can happen out here. First, you gotta make the leap.

2) Breaking Away - How to Start Traveling

For most people, this is the big one. You may be tentative about travel because of some real or perceived barriers. I sometimes call them anchors. These are things like:

  • Girlfriend/boyfriend/spouse
  • Your job
  • Your apartment/house
  • All of your stuff
  • Friends, family, kids

Besides these anchors, there's also the fear of the unknown that holds people up — wondering how you'll make money and what your day-to-day might actually look like. I'll cover that in the next sections about travel logistics and sustaining a life of travel.

First, let's address some of these common anchors. Enjoy this simplified flowchart.

OK, so that makes it pretty simple, but let's get into it a little more.

Your significant other and your need to travel

Let's start with your boyfriend or girlfriend or what-have-you. If it's not that serious, well then that's easy — goodbye!

The issue arises when it's "serious" and they're not interested in traveling with you, nor are they OK with you taking off for a while. All I can say to that is: this is your life. This is it, happening now. If travel is essential to you, if it's something you yearn for, then go for it.

How serious is this relationship, really? Do you want to be with someone who would disallow you to be you, to expand? Someone who doesn't share your interest in travel? Are they worth that compromise? You need to assess the balance.

I've met far too many people who regret not traveling when they were younger*. Many of them have cited the girlfriend/boyfriend excuse and guess what? Often they're not with that same person anymore, or worse, they're with them and resent them. At the very least they wish they'd tried harder to make something work, no matter how in love they were and still may be.

*Younger is relative. I've met people in their late 20s who think it's "too late" to travel, they're too "dug into society". On the flip side, I've people in their forties, fifties, sixties, and older flip the switch and hit the road. All it takes is a mental click.

Your job

The job anchor is usually a much easier one to tackle. Most of the time people are nervous about what they'll do for money, not quitting the job itself. If your job sucks, it's real easy to pull the plug.

Those who do like their jobs usually like the people they work with and their boss, so most times, these same people will fully understand and respect your need to get out and travel.

A girl I was seeing from time-to-time went through this when she wanted to drop everything and hit the road with me. She was ready to quit the job that she rather liked in order to join me. When she went to quit, not only did they understand, but they told her she could call it a "leave of absence," take as much time as she needed, and if she wanted, the job would be waiting for her when she came back.

Of course, especially after a goofy 2020, more and more work can be done remotely. You don't necessarily want to be working forty hours a week on your computer while you're traveling, but on the other hand, wouldn't you rather be traveling?

Dealing with your place and your stuff

If you're renting an apartment, you'll decide whether to cut loose or wait until your lease is up. For some people, this is actually the exciting part. It makes it real.

Let's say your lease is up at the end of May. Well, that's it. That's when you hit the road. It takes the guesswork and second-guessing out of the equation. You have a date to be excited for; you know how long you have to get ready, and you can even make definitive plans for your first destination.

If you own your place, you'll figure this out too. You know your own situation, and you likely need to sell it, rent it, or maybe you can afford to just leave it as is.

As far as stuff, this is a great time to purge. Get rid of everything you won't be traveling with or find some storage.

Personally, I didn't have a great deal of stuff. I lived in a New York City apartment with friends who gladly inherited my futon and dresser drawers, cherry-picked clothing, and I gifted them much of my audio equipment as well. What wouldn't fit in my backpack went to goodwill or the trash.

The feeling of freedom is stronger if you can get rid of everything. If what's on your back is all you have to be responsible for in the world, you're doing pretty well. But if you simply can't part with your junk, then hopefully you can afford storage or got a good friend with some space in their basement.

One tip, if you've got a bunch of functionless nostalgia, consider photographing it and then giving it the heave. Do you really need the clay fish you made in grade-school clinking around in a box somewhere, or will a photo make you smile just and much?

Travel with or without Family, Friends, and Kids

Your family and friends may be encouraging, discouraging, or indifferent. It really doesn't matter. Once you're out there having a good time learning and growing, they'll come around. Or not. Unless you have some direct responsibility to someone, a slack that no one else can pick up, then you should go live.

You'll get on the road and like it, love it, and maybe even stress out at times. As long as you give it enough time, no matter what unfolds, it'll be one of the most important things you've done and a memory you always draw from.

The same friends and family that questioned your decision may be the same ones you inspire to do the same. Or at least inspire them to make some other leap in their life.

You may decide to hit the road with a friend or significant other. Traveling together can strengthen your bond and leave you with lifelong memories, but can also be taxing on even the tightest of relationships. Too much time together, often making significant travel decisions and getting to know each other's quirks, can lead to unexpected rifts or resentments. This isn't always the case and isn't always extreme, but it's not uncommon.

All I'll say about this is to prepare for the possibility of being on your own, either right away or down the road. If your partner gets cold feet when it's time to go, don't let that hold you back. And if you get sick of each other (hopefully just temporarily), or they just burn out on travel while you're still in the flow, be prepared to switch gears to a solo-mission.

If you've got kids, things become a bit tricky, but there are options. You can definitely bring them along. I can't pretend to be an expert on this, but I have met people who've hitchhiked around the world with a one-year-old baby and people who've home-schooled their older kids on-the-go. I've met couples and divorced couples who've taken turns with the kids.

Obviously, a lot hinges on how many kids you have, what their ages and vibes are, and any other parent/guardian involved. Get creative, or just do a Google search for something resembling your exact situation. I just did a search looking for someone's blog about hitching with their kid I met (couldn't find it, I think the domain expired) and there were dozens and dozens of examples of people traveling with their kids in different ways.

Besides some edge cases, hopefully, that covered most of the potential anchors holding you back from your adventure. Maybe you weren't even worried about any of that. Perfect. Let's get into some logistics of travel to give you some more confidence in what's possible.

3) Travel Logistics

Often just hearing about the basics of travel is enough to get the juices flowing. I'm most asked about what to pack, how to get around, and where to sleep on-the-go. I'll explain some great options, then we'll get to the last section about money and sustaining a life of indefinite travel.

Packing for indefinite travel

So, jumping from leaving your stuff behind, you'll probably wanna bring some stuff with you — namely a backpack full of essentials and not much more.

Packing for travel is something I've written about, made videos about, and talked about on my podcast many times — as have thousands of other people in every corner of the internet.

For a deep dive into travel packing, I suggest the following extensive resources I've put together:

Read: Ultralight Packing Guide for Freestyle Travel

ListenUltralight Travel Packing from Freestyle Travel Show (my travel podcast)

Watch: Packing for versatile long-term travel (Less than 15-pound backpack) from my YouTube channel

To sum it up, you want to travel as light as possible. The smaller and lighter your bag is, the freer you'll feel wandering around a new city or covering miles on a hiking trail. You'll also avoid hassles and fees whenever flying.

The links above will get into the amount and types of clothing I recommend, why being able to camp is nice and what gear is best, toiletries, electronics — everything you need and nothing you don't.

Getting around

Readers of this blog and viewers of my YouTube channel know that I'm an avid hitchhiker. Regardless if I have money, this is the first option I consider if there's a road that leads to my destination (people hitchhike on boats too!).

Hitchhiking is free and not nearly as "scary" as an inordinate amount of people seem to think it is. Some of my best stories come from all the people I've met, the conversations I've had, and friends I've made while hitchhiking. Often traveling like this is much more than a free ride to your destination, it can be the heart of your adventure itself.

If you want another deep dive, I have a page devoted to hitchhiking advice with links to podcast episodes and videos as well:

There are many more ways to get around besides hitchhiking of course, and sometimes it's not an option or simply not the best option.

You may even decide to have your own transportation, like living that van-life or cycling from town to town, or maybe getting a motorcycle or even a sailboat.

Personally, I don't want the expenses, responsibility, or maintenance hassles that come with any of that. At least not long term. Yes, they offer you certain freedoms, and for many people that alone is worth it. Maybe that's you. Go down any road on a whim, sleep in your vehicle, get up and get moving at any moment, and better estimate how long it'll take to get wherever you're going.

If you're like me, however, then the main options are walking, hitchhiking, buses, trains, planes, and the odd road trip with friends or transporting someone else's vehicle.

I'll usually only take a bus if I'm on a certain time-crunch or the weather is just horrible, it's super-convenient and I can actually afford it. MegaBus and FlixBus are low-cost buses to check out, sometimes just a dollar or two to travel hundreds of miles. Another classic travel trick is to take an overnight bus or a train instead of getting a room for a night. You can spend $40 on a room, or you can spend it on a ticket where you sleep through the night and wake up wherever you were heading to.

I've gotten pretty good at finding cheap flights when I need to, usually for getting over oceans. I talked about some of my strategies on an episode of the Freestyle Travel Show here:

Since you've made it this far, and if you're liking what you're reading, you should probably go ahead and search for "Freestyle Travel Show" in your favorite podcast app and subscribe. I record one or two episodes every month talking about my recent travels, specific travel topics, or with people I meet on the road.

Anyhow, the main thing with finding cheap flights is being flexible. That episode gets into the sites I use and how I use them ( is my favorite), but it comes down to being flexible on dates and exact airports. For example, if I'm in Texas and I'm itching to see a friend in the Netherlands, I'll gladly hitchhike to Florida and catch an $80 flight to Barcelona, then hitch north to see him rather than pay hundreds of dollars more to fly direct today. If I'm not in a hurry, I'll wind up enjoying the bonus adventure in between.

Where to sleep while traveling

Once again, this is a topic I've shared loads of information on. I highly suggest you check out this page ( to get tons of deeper info and further links to my podcast and videos on the subject of where to sleep while traveling.

This is where historically I've suggested, however, those glory days are seemingly over*. Never fear, other sites have picked up the slack, namely Trustroots and Belwelcome.

You can use Trustroots to connect with friendly locals while you're traveling the world and stay with them for free for a night or three. Unlike Airbnb, Trustroots is about meeting local people and often making a friend — as well as the free spot on their couch, floor, spare room, or yard to camp in.

Airbnb is often cheaper than a hotel room, and can be a good option if you want some cheap privacy and security for the night. Use Trustroots if you want to be social, use Airbnb if you don't (although you'll occasionally make friends there too).

The cost of a bunk in a hostel room can cost as little as a couple bucks in some parts of the world, and tens of dollars in other places. They're different everywhere, but often they can be social hubs.

Trustroots and camping would be my primary advice while traveling, but check out that link above if you're curious about everything else I do from camping to hostels, to friends, new friends, using social media, and more for sleeping while traveling.

*Couchsurfing started charging money in 2020 and went about doing so in a pretty clumsy way, to put it gently. Their execution of such has nearly rendered the site useless, even for those willing to pay.


We all know about email, Facebook, and Instagram, etc. Staying in touch is pretty easy.

WhatsApp is not as common in the United States but has been the standard messaging app in most other countries. People have switched to Signal and Telegram as well. Do yourself a favor and check these apps out; it's nice to exchange contact info with people you meet quickly, no matter what platform they may use.

It doesn't hurt to jump on all the payment apps too, like Venmo, CashApp, Paypal, etc. Hell, get a bitcoin wallet as well. You never know when you'll have to pay or get paid via one of these methods and having it set up already could be the difference in whatever transaction is going down. Also, it's nice to have backup options if bad-times strike and you get pick-pocketed, mugged or otherwise lose your wallet.

Many parts of the world have free Wi-Fi readily available, at least in cities, but getting yourself cell service can lend you more freedom. I suggest Google Fi, which is Google's international phone service. It's $20 a month for unlimited texts and calling plus $10 per GB of data used. It works in nearly every country in the world without any fuss or a contract.

If you're gonna be in one country for a month or so you can always look at getting a cheaper local sim card and just pause your Google service (and therefore not pay) until you need it again.

4) Sustaining a travel lifestyle

So you've wrapped your head around your potential travel rhythm and style, how to break away, and you're excited seeing how this can logistically become a reality. Perhaps you're still wondering, though, how you can afford to do this and just how long can you last out there. And is this goodbye?

Folks love their money

Yet again, I've got your back. I've got an entire page devoted to travel expenses, saving money, and making money while traveling. That'll give you plenty to read, watch, and listen to on the subject.

You can travel with millions of dollars and you can travel essentially for free. You can head out with a bankroll, you can incorporate work into your travel flow, or you can intermittently pause to earn money.

Obviously, keeping your expenses to a minimum is very helpful. Traveling indefinitely is very different than a two-week resort vacation. That brief vacation may cost as much as several months of living-at-home expenses, so people tend to extrapolate that and think that anyone traveling indefinitely must need to have gobs of money saved up. Nope.

First, when you're traveling indefinitely you're not staying in hotels every night, pressured into pricey excursions every day, fine dining, and the cost of a single plane ticket is spread over months instead of days. If you drop the coin for a flight to Australia, it's well worth it if you enjoy the full 90 days allowed on a tourist visa instead of one week.

Second, you no longer have the typical expenses of living in one place, such as rent and utilities.

Also, you may be in a place like Thailand where the cost of living may be remarkably cheaper than where you were living before. Namely, things like food and booze won't set you back nearly as much day-to-day as they would in any city in the US.

Where does the money come from? I share plenty of examples in the link I gave you above. I've been able to make money doing odd jobs for people, helping with harvest seasons, starting my own projects, writing a book, and even from this blog via ads and affiliate links.

There are thousands of ways to make money remotely now, especially after all the fun in 2020. When you see a lady on her laptop at the hostel, you never know if she's raking in six-figures working for Twitter, translating a document from French to English for a hundred bucks, designing a logo for a cosmetic dealer across the world, or just death scrolling on social media.

Again, check out my in-depth page about spending and making money while traveling, as I also brush on travel work-exchange programs where you can work at farms, hostels, and other cool places for room-and-board.

Making arbitrary budgets are insane and probably stressful. But maybe that's your style. Google around and you'll see people bragging about living on $50 a day, $5 a day, whatever a day, and maybe they'll even charge you to read how. In reality, we're all different, and no matter where you go the costs of things vary from free to ridiculous. In the end, you choose your adventure.

The best thing you can do is just go out and live. Try not to spend more money than you have, and when funds get low, an opportunity will usually arise. An idea will emerge. You'll be stronger by then anyhow.

Is this goodbye?

I'm often asked if I miss my family or my home. My friends. If I'm lonely.

Nope. Going traveling indefinitely doesn't mean cutting everyone off. It also doesn't mean you won't pop in on the family for a holiday here and there. And it means you'll have a chance to visit all those friends and family who may be scattered around the country or the world.

Social media, video chats, phone calls, and texting aren't the same as hanging out in person. But it's pretty damn good. There's plenty of people among us who didn't have that growing up, so it's easy to still associate traveling to being out-of-touch with friends and family.

There's plenty of times I visit a familiar friend in a familiar city and ask, "how's so-and-so?", referring to a mutual friend in town, and they respond that they haven't hung out with them since the last time I was around. Even great friends will get caught up in their personal lives so much, that "the other side of the city" is like "the other side of the world." When you're actually coming from the other side of the world, and only in town for a week, somehow both sides of town come together.

Traveling is incredibly social if you allow it to be. On an average day of hitchhiking, I may get three or four rides, and sometimes I'll get ten or fifteen. Usually, if those rides are longer than thirty minutes, I may end up having some pretty deep conversations. I've even wound up making lifelong friends.

Staying with people through hospitality sites or at hostels results in the same types of great conversations and just hitting a good local brewery produces friendly people.

You never know when you'll turn the corner and fall in love or find your newest friend.

Go out and travel!

I hope you have an absolute blast. Have an excellent time, and maybe our paths will even cross.

Feel free to poke around this site some more for information and inspiration, and feel free to comment on this post with questions or insight. I've got hundreds of travel stories and pieces of advice on specific travel topics.

There's also the podcast, Freestyle Travel Show, and the Hobo Lifestyle YouTube channel with adventures and advice.

Then of course @HoboLifestyle in Instagram, Facebook, and Twitter for whatever I may be posting.

Happy travels, I'll see you down the road!