How I traveled around the world for six months (and made money doing it)

My wife and I packed, leaving behind the apartment and furniture we sold
My wife and I packed, leaving behind the apartment and furniture we sold

My wife and I knew we wanted to travel, and with about $10,000 in the honeyfund account we set up in lieu of a wedding registry, we had enough for a pretty epic honeymoon. I, however, like to stretch the limits of possiblity. Why have an epic two-week trip when we could stretch it out into an even more epic six month trip? All we had to do, I reasoned, was spend our money wisely and work a little while on the road.

Now, just for perspective, $5,000 per person (what we had in the honeyfund) is about what a normal American might spend for a nice trip to one or two European countries, including airfare, hotel, ground transport, entertainment, drinks, and meals in restaurants for two weeks. We managed to travel to dozens of cities in seventeen countries across four continents and went all the way around the globe. Here’s how.

1. Control your expenses

My two biggest expenses were my apartment and my car. So, I got rid of them. I sold the car and house. The reason to sell your things is not to use that money for travel (put it in a savings account and don’t touch it!), but to stop having to spend money on a life at home you’re no longer living. Without a mortgage, utility bills, car payment, or car insurance, my monthly bills dropped from thousands to hundreds, which freed up a lot of money to travel with. We put all our stuff that we didn’t sell in a month-to-month storage warehouse, which only cost $120/month, and I paid the bill each month via PayPal from wherever I was at the time. If you want to do a short trip, try renting out your car and/or home (just be really careful you don’t invalidate your auto insurance or lease in the process). If you rent your home or lease your car, you probably can’t legally sub-let them, which is why I highly recommend that you…

2. Travel longer

Getting rid of or renting out your home is more hassle than it’s worth for a short trip, but is worth it if you want to travel for many months or even years. If you do a longer trip, you only pay for the bed you’re sleeping in, and not the bed you left behind at home. By paying for one bed to sleep in instead of two, you avoid doubling your daily expenses.

If you’re working part time and earning income while you travel, that’s time you won’t be able to spend out and about in your new surroundings. If you’re working half the time, spend two or three times as long in each place as you normally would.

3. Maximize your income

By working while you travel, you can live on your earnings instead of your savings, which is definitely preferable. Arranging a job you can do while traveling is tricky, however. Getting a job with a foreign company will just tie you down all over again, assuming you can even get a work visa and decent wage.

To keep working while you travel, it’s best if you can keep a job you already have. This takes some time to set up and a little luck, but it’s doable. If you are able to do your job remotely (online or over the phone) from your home while living in the US, there’s no compelling reason why you can’t just keep doing that job from a different country. The only hard part is getting whoever is paying you to believe this. If you are able to get set up with some sort of online business before you go, that would definitely be the best way to do it. If your current job can’t be done remotely, try getting a part-time job as a virtual assistant either on your own or through a company like a few months before you leave, then keep it while you travel. Just be prepared to work US hours when overseas. This might mean working in the middle of the night, however, the upside of working nights is that you have your days free to explore whatever country you happen to be in.

If you happen to be a computer programmer, you can find all sorts of interesting jobs that can be done from anywhere. is a good source, and is curated by Pieter Levels, the guy who runs, which is another good resource for globe trotting techies.

My office in Bangkok, Thailand, working well into the night for my US client that was 11 hours behind
My office in Bangkok, Thailand, working well into the night for my US client who was 11 hours behind

I essentially out-sourced a job to myself. My company needed to hire someone with very specific computer and research skills but was having trouble finding that person, so I quit my full-time job as a VP managing staff, then in the same meeting asked my boss to hire me back as a freelancer doing this other job that could be done entirely online and over the phone. This was a big gamble, since they could have said no, and they could have ended my freelance employment at any time while I was traveling. I assumed the arrangement would last about three months and budgeted for that, but it lasted eight months before they found a full-time person to take over the job. In other words, I was employed the entire time I was traveling, which meant I never had to dip into savings and could pay “rent” (a.k.a. hotel and airbnb) and “car payments” (a.k.a. planes/trains/rental cars) out of my monthly income, just like I would any normal month living at home.

4. Spend money upfront to make working on the road easy

It is amazingly easy to work from anywhere in the world if your job is done on a computer, but you need to invest in a flexible mobile hardware and software set-up that is fully backed up to the cloud should your gear get lost or stolen. I used a MacBook Air (running Windows as a virtual PC with VMWare, Adobe Acrobat Pro to “sign and scan” documents digitally, and Dropbox for full back-ups) and an unlocked iPhone.

My office in Dubrovnic Croatia
My office in Dubrovnic Croatia

I got a global data plan from AT&T, which allowed me to answer calls, tether my computer, or quickly respond to emails anywhere in the world. To avoid burning through too much cellular data, I would do most of my backups over hotel wifi and would often use Skype for calls or video chats and screen-sharing. It was necessary to have the option to tether my computer to my phone and use cellular data, or use wifi, since cellular data gets expensive but wifi isn’t always available. With both options available, it was truly rare that I had trouble getting online as long as I stayed in decent sized cities. Just like in the US, however, once you get out into the countryside, finding a cell signal gets a lot harder. When choosing between that mountaintop Tuscan villa or a Parisian loft, exchange a few emails with your hosts first to see what the cellular phone, cellular data, and wifi situation is. I learned the hard way that many hotels “with wifi” only had it in the lobby. AirBnB hosts, on the other hand, tended to have great wifi right in the apartment.

I found the global data plans offered by US carriers to be underpowered and/or expensive, and any normal user will burn through their allotment of data very quickly. So, before I left, I unlocked my iPhone, which meant I could swap out my AT&T SIM card and get on a network anywhere in the world. When I landed in a country, I would use my global data plan for the first day (mostly for Google Maps, Facebook check-ins, and translation apps), but then quickly find a local cell phone store and get a new SIM card. Deals will vary by country and carrier, but I would usually pre-pay for 5 to 50 gigs of data, whatever about $50 would buy me. Once you have your local data plan, you can forward your US cell number to a Skype number, and answer or make calls on the mobile Skype app.

5. Make your bank accounts globally accessible

First, establish a “home” setup that works for paper mail. It’s important to make sure you set up and maintain a US-based home address while you’re traveling, particularly if you are working on the road. Ironically, you can’t get a global cell phone plan, global bank account, or travel insurance without a home address. You can pick a mail service, or a relative’s house, but you have to have a US address to send paper bills and checks to (and so the state and federal governments get their cut of your taxes since you’re still a US-based worker, remember?). Make sure someone you trust is there to open your mail in case something important shows up. If you can, arrange for pay via direct deposit before you leave the states.

Next, make sure you can access your cash wherever you are in the world. I opted for a Schwab Checking account, which allows you to get cash out with no foreign fees or ATM fees, anywhere in the world, and got a credit card with no foreign transaction fees, and pin and chip functionality. Make sure to call all your banks and credit card companies the first of every month to let them know when and where you will be traveling over the next month so they don’t shut down your accounts because of a fake fraud trigger. It’s also a good idea to use one card for your recurring bill payments, and a different card for everyday purchases. That way if you lose your everyday card and need a replacement, you won’t have to update the card on file with every auto-pay account.

6. Pay for travel with travel on credit

There are lots of points systems out there, but we opted for the Chase Sapphire card. It has a chip and pin, which means you can use it just about anywhere in Europe (they will not accept swipe and signature credit cards most places), it has no foreign transaction fees, and you get double points for buying anything travel related, which means that if you book all your travel for the first half of the trip on the card, you will quickly earn enough points to travel free for the second half of the trip. We paid for all our travel on the card up until we got to India (half-way around the world) but booked all our flights from there on out with free miles. Also, if you have to stay in hotels, try booking through, since they will give you one night free for every ten nights you book through them. Sure, you could use a hotel rewards program like Starwood or Marriott, but that will really limit your experiences abroad, which completely defeats the purpose of travel.

7. Stay safe for cheap

American health insurance is really expensive, but travel insurance is actually quite cheap. If you can, get rid of your US health insurance and get travel health insurance. We got a plan through that was super-cheap and covered us anywhere in the world. It even covered our belongings if they were stolen. If you read the fine print, however, there was a big catch with the travel health insurance plan we got. It would not cover us in the event that we injured ourselves while under the influence of drugs or alcohol. Make sure to read the fine print!

When you return home, you will probably want to get a new US-based health insurance plan, but this can be tricky. Open enrollment periods only happen during November to January, which means if you get back from your travels in June you’re stuck without insurance until January 1st. A good way around this is to plan ahead to make sure you have what’s called a qualifying life event. Qualifying life events include marriage/divorce, getting a new job, and (very helpfully for the traveler) moving to a new state. If you lived in, say, New York, and designate a relative’s house in Ohio as your permanent address while traveling for six months, then go back to New York and change your permanent residence back to New York, then you technically just moved from New York to Ohio, then back to New York, which is a qualifying life event. Don’t hate the player, hate the game.

Another loophole I found in travel health insurance is that it will cover you until you get within 100 miles of your home. However, your home is just where your stuff is and where your mail goes. Upon returning to the states, if you sublet a place more than 100 miles from “home”, then you’re technically still traveling and can be covered by travel health insurance while in the USA.

8. Live like a local

At the time of our travels, we found AirBnB locations to be common throughout the world, though more prevalent in big cities and more developed locations. In destinations like London or the south of France, hotel prices tended to run upwards of $300 per night, but renting someone’s apartment on AirBnB was roughly $80-$120 per night, came with wifi, laundry, a kitchen, and was in a neighborhood full of locals instead of tourists.

Having a kitchen will save you a lot of money over a six month period, since you can shop at the local grocery store and cook for yourself. In my opinion, exploratory eating is one of the best parts of being in a new place. It may take a week before you find the best local market, but haggling in the market for fresh meat and veggies, or inviting new friends over for a dinner party, are some of the most rewarding experiences you can have as a traveler. If you want to speed up the process, spend a little money on a cooking class the first or second night you’re in a new place, then grill your teacher for info on where to shop and where the best non-touristy restaurants are. Cooking classes are a great way to get educated on the local cuisine while making friends.

The TripAdvisor app is a great way to find cooking classes with high ratings and reasonable prices. It’s also a good way to find tourist-friendly businesses in smaller towns. However, in big cities, the app will steer you towards the same sights everyone else is waiting in line to see.

When getting around, find out how the locals do it. Most cities with trains have smartphone apps you can use to navigate them, or come pre-loaded on Google Maps, which can really help when navigating a strange system. Taking the train or bus usually costs a fraction of what you’ll spend on cabs, and many cities have “tourist passes” which offer unlimited rides for a week or a month. Just budget lots of extra time at first so you can figure it out, and don’t be afraid to ask for help. Save all that cab fare money for the 2am trip home from a bar or the frantic dash to the airport for an early flight.

9. Travel to the deal, not the destination

Europe and Asia are full of discount airlines that offer cheap local flights. If you’re flying from the US, try booking your initial one-way flight to an interesting city that is also a big airline hub, like Copenhagen or London. Scanning the European flight deals, you can find dirt cheap flights from these cities to destinations all over Europe and Asia.

We used an app called SkyScanner, and very rarely booked our flights more than two weeks in advance. With, you simply put the dates you want to travel, and the city you are starting from, then it will list out every flight leaving from that city to every location around the world, in order of price. Perhaps Aix en Provance wasn’t initially on your radar, but you see on SkyScanner that there’s a $50 flight from Copenhagen. Book it! Then, figure out where you can go to cheaply from Aix. Check the local train systems for deals too. Just Google “French Train” or “Spanish Train” and you’ll quickly find the local websites (SNCF in France, RENFE in Spain, etc.). Be advised that each country has it’s own system, and you’ll want to book based on the country you’re leaving from. Train deals will be scarce during the prime summer vacation months, but you’ll find lots of deals during the fall and spring off-season. Sure, you could buy a Eurail pass, but you’re  really unlikely to save much money, and then you’re locked into train travel and can’t hop on the $80 last-minute flight to Morocco.

One caveat, before you book that last minute flight to Russia (or anywhere else), check the US State Department website to see what the visa requirements are. It’s no fun arriving in a new country only to be put back on the plane and sent home because you don’t have the required visa. We went to considerable trouble to get a tourist visa for India before we left the US.

10. Stay longer in each city

Spending two weeks in a city might feel like a luxuriously long time, but trust me, it will take a week and a half just to feel like you have the place figured out, especially if you’re stuck working on your computer for three or four days at a time. I highly recommend spending four weeks or more in big cities, and two weeks or more in small towns.

By moving less, you save a lot on airfare, you’ll find more locals-only deals, you’ll make more friends, and you’ll have a much more authentic experience. If you insist on excitement, try booking a different AirBnB apartment every week in different neighborhoods. That way you can cover much more ground around a city and really get a feel for the difference between the laid-back residential neighborhoods and the up-all-night trendy urban neighborhoods. Or, slum it one week and go posh the next. The point is that you can travel to very different experiences with just a $2 train fare.

If you find a place you really like, stay or come back. If the place you scheduled three weeks in is terrible, leave. Most hotels will refund a cancelation up to the day before you booked, and when booking AirBnB homes, you can set the search parameter to exclude locations with strict cancellation policies.


This list is certainly not comprehensive or static. The world is a quickly changing place, and you should do your own research before blindly trusting anything above. I will readily admit that this advice is meant for neither the budget traveler or the luxury vacationer. What I hope is that this helps people in a middle-class situation similar to my own realize that travel can be a comfortable way of life, rather than just a break from life.