Long Term Travel FAQ for a Digital Nomad

Thinking about working remote as a digital nomad? If so, this long term travel FAQ is for you. I’ve been traveling full time around the world for 14 months now, and I’ve learned so much along the way. From packing tips to where to buy flights and everything in between, here’s all your questions about long term travel answered!

How Long Should I Stay in Each City?

After a lot of trial and error, I’ve found what I think is the best length of time. Unless a place is truly amazing I like to spend 5 weeks in each city. So, what that looks like is:

Weekend one: Arrive on a Saturday night or Sunday
 Weekend two, three, four, and five: four full weekends to explore the area
 Weekend six: Travel to new city

We tried traveling on weekdays but with work it was just too annoying. Either trying to get stuff done on busses or flights, having to get work done ahead of time to make up for a lost day, or telling clients we’d be unavailable, it just wasn’t worth the hassle. Surprisingly, traveling on weekends hasn’t been any more expensive than on weekdays, and it’s so much more fun to arrive in a new city and hit the bars or have a day to explore instead being stuck inside with work.

We stayed six months in Medellin and that was WAY too long. Then we stayed two months in Cusco, and finally started just doing five week stays. With four full weekends, you can see the two or three most touristy things in an area, but still have time to get off the beaten path as well.

How Do I Book Accommodation?

Good question! I 100% recommend Airbnb, and it’s all that I use. It’s great because if you stay for one month or more, hosts almost always offer discount, sometimes up to 50% off. We rented outside of it once in a foreign country, and it ended in disaster.

If you’re DEFINITELY set on staying off Airbnb (admittedly the prices are usually higher, but it’s a worthwhile trade off for security) then check out local Facebook groups to find a place to rent. Just search the city + expats, or rentals, and there are usually plenty of groups. For more info, read How to Rent an Apartment in a Foreign Country.

Taxes Seem Complicated… Explain Them

No. Honestly, I’m definitely not qualified to help anyone with their taxes, so the only thing I’ll do is explain my own. When Daniel and I taught in the UAE, we did not have to pay taxes in the United States because we were out of the country for long enough each year (I think it’s like 330 days?) and because we did not make enough to be “double taxed” (the income amount is something like 90k).

Once we started freelancing, things changed. We filed as an LLC in the state of Ohio and all of our money from work went through one specific bank account that we then paid ourselves out of. Because we were an LLC we had to pay “estimated taxes” four times a year instead of just once.

I’m still freelancing and using this method of tax payment. No matter where I live in the world, I pay taxes to the US just like I’m living there. Daniel has a full time job now, and pays taxes in the US like normal too (despite us mostly being abroad).

Basically, if you are a freelancer, you will probably have to pay taxes in the US even if you never step foot inside it. If you have a full time job abroad, you probably will only pay taxes to the country you’re in, unless you still spend a lot of time in the US still or are making mad money.

BUT like I said, absolutely every situation is different and definitely research into your own job and finances. DO NOT take my word for it because I do not want to be sued! Thanks!

What Health Insurance Should I Use?

Ugh, health insurance. It’s different for every country, so this info is going to be targeted at Americans. When we first started traveling full time, I was on my parent’s health insurance still and didn’t need to do anything else because it covered me abroad.

Dan was over age 26, so he purchased travel insurance. This covered him in every country EXCEPT the United States. The cost was around $250 for six months. This plan was great because we spent no time in the US in 2017 until November. (Be careful though, because some travel insurance carriers require you to ALSO be covered with a US health insurance plan… make sure yours isn’t like this.)

When we returned to the US, neither of us were covered by a job because we were both freelancing, so I bought healthcare through Healthcare.gov. It was a crap plan for about $50 each per month and didn’t cover us while traveling. Soon, Daniel got a full-time job and with that came a healthcare plan in the US. We still have to buy travel insurance on top of it to be covered outside of the country though.

Basically your options are to get a US health insurance plan and double up with the travel insurance, OR if you’ll be abroad all year, find a travel insurance plan that does not require a US health insurance plan as well. If you’re planning to be in the US at all, it’s probably easiest to just pay for a cheap plan year round and get it off your plate.

PS This is only based on my own experience and should not be taken as fact, you should research everything before you choose the correct plan for yourself (aka don’t sue me).

What Should I Pack?

The first time I left the US on a digital nomad, I packed wayyyyy too much. Keep it light, and you’ll be so much happier when you’re moving every month.

For clothes, I usually pack two or three dresses, a pair of jeans, a pair of leggings, four or five t-shirts, workout leggings, six to eight nice shirts, bra, sports bra, strapless bra, underwear, jean shorts, and pajama pants.

I also pack a cardigan and super lightweight fleece jacket.

Hiking boots, running shoes, and flip flops generally suffice, if you want “cute” shoes you can also pack a pair of fashionable boots as well.

Outside of this, I usually pack a toothbrush, toothpaste, makeup, shampoo, conditioner, and face wash (if you’re checking the bag), razors, sunscreen, hair ties, bobby pins, and medicine (call your insurance ahead of time and sometimes you can pick up three, six, or even 12 months of your prescription early).

Finally, throw in a kindle or a couple books, laptop, phone, portable power pack, a speaker, all chargers and cords, a deck of cards, a coloring book and colored pencils, wallet, jewelry, and sunglasses, and you’re good to go.

Do You Have Any Travel Products You Recommend?

Yes, definitely! Some stuff I really love and use all the time is listed below:

Osprey Backpack

This bad boy is the BEST. It’s pricey for sure, but definitely worth the investment. The Osprey Farpoint 55 is all I use.

Some reasons why it’s amazing are first, it’s carry on sized for most major airlines (not budget ones though) so we can save money on checked bags. Also, it has a second small backpack that you can zip to it! I use the large bag to store all my stuff when moving from one place to the other and for long camping and hiking trips, but I still have the small bag for day to day use.

Did I mention that the entire front opens like a suitcase, so you don’t have to go digging into it every time you need something like a traditional backpack? And finally, Osprey products have a life time warranty, so you can always get it replaced if something goes wrong. If you want to become a digital nomad a rolling suitcase just isn’t gonna cut it. This Osprey bag has everything you need for long term travel.

Vibrant All in One Travel Bottle

I got this for Christmas and am so obsessed. I love the sleek look, and functionally it’s even better. This thermos keeps hot water hot for SO LONG, and cold stuff cold for ages. It also has a strainer at the top to make fruit infused water (my new obsession) or steep tea. For a day to day water bottle, I couldn’t ask for more.

Timberland Boots

The first time I bought hiking boots I was in the UAE. We went from mall, to mall, to mall because all the stores had the tiniest female selections and sold boots almost only for men! So sexist. I finally found a pair of Timberlands. They were expensive and I was on the fence, but I pretty much had no other choice but to buy them.

That was three years ago in Spring 2015 and they’re still going strong. The boots are cute, comfy, and seriously hold up on even the toughest hikes. I wore them on a seven day trek through the Himalayas in Nepal, on the Santa Cruz and Salkantay four and five day treks through the mountains of Peru, scaled a 19,000 f.t volcano in them, and walked through the streets of Europe for miles at a time. They still feel like new even after all that. It’s love.

UE Boom Speaker

Daniel introduced me to the world of quality sound and speakers, and I can’t go back now. We often stay in Airbnb’s with crappy TVs or even no TV, and watch shows on our laptops. Even just for music day to day, this speaker is amazing.

The bluetooth speaker is easy to use and carry around with us, it’s water proof, and the sound quality is amazing. Even after getting chucked in our bags and dragged from country to country over the last year, it still works perfectly.

Sprint International Phone Plan

Nomadic Matt recommends the TMobile plan for international travelers, but I heartily disagree. I vetted TMobile, Verizon, and AT&T before I made my choice, and Sprint has far and away the cheapest plan. I get to keep my US number, have unlimited calls and texts to any country in the world, and 1gb of international data. When I get back to the US, I also have 2gb of domestic data.

Landing in a new country, switching on my phone, and immediately having data is honestly the height of luxury and makes travel SO easy. Just having GPS in our day to day life abroad is invaluable. I definitely recommend the Sprint International plan for all digital nomads and long term travelers.

How Can I Work and Make Money While I Travel?

There are PLENTY of different ways to do this. If you want to work abroad you can teach in Dubai with very little qualifications, or get a job working on a yacht. If you don’t want to be tied to a location, no matter how exotic it may be, you can become a freelance writer or digital marketer, or teach ESL classes online. Visit the Working Abroad page to learn more and see step by step guides for each one.

How Can You Live and Work in Different Timezones?

Timezones are seriously the lamest. They suck, I know. For the first 14 months that we worked remote as digital nomads, we stayed in timezones close to the US in Colombia, Peru, and Mexico. Daniel has a full time job and is tied to the American nine to five.

We’re throwing caution to the wind though, and in the spring we’re heading to Eastern Europe, where our work day will be from 4pm to midnight…. yeah. I’ll report back and let you know how that works out. I actually think it might not be too bad but we’ll see.

As a digital marketer and writer I have had clients in England, Singapore, the Philippines, and Australia, so working outside of your client’s timezone is definitely possible, it just slows down communication a bit. If you really have your heart set on traveling Asia, your best bet is to teach ESL classes online, because you will be working within Chinese timezones.

How Do You Decide Which Countries to Visit?

The AWESOME thing about long term travel as a digital nomad is that pretty much nowhere is off limits. There are sooo many places that I want to explore that I actually sometimes get really overwhelmed when I have to choose just one for our next stop. These are the steps I usually take when deciding which countries to visit, and some things you definitely need to keep in mind.


First things first, look for the cheap flights. Use Skyscanner, and search from the major airports around you to “everywhere.” I live in Ohio, so I always check flights from Cincinnati, Chicago, and Detroit to find the best deals. If you live near major hubs sometimes its worth using them to save money, especially if you’re traveling for a long period of time.


Once you narrow down the countries that you have affordable flights to, the next is to check the cost of living in each one. Just because Norway is $100 cheaper to get to than Romania, it doesn’t mean it makes financial sense to choose it. You should also make sure it’s a good city to live in. Google things to do there, restaurants, nightlife, and day trips to make sure there’s plenty to fill your time.

Cost of Living

After you’ve narrowed down the countries that are affordable to get to AND live in, it’s time to check on the accommodations. Like stated above, I always use Airbnb. So, search the cities you’ll be staying in for the dates you’ll be there. Are there a lot of options that look nice and affordable? If there’s only one or two listed in the area, that will be a risk.

If flights, cost of living, and accommodation all check out, you need to make sure internet speeds in the city are good before you move there. Finally, check out the visa situation to ensure you can stay long term, and don’t need to take any extra steps to be approved to visit.

Once this is ALL finished I book the flight and accommodation, usually a couple months ahead of time. Everything else like local transport and planning what to do waits until we arrive.

How Much Money Will I Spend?

Pretty much as much or as little as you want. It REALLY depends on the country you choose. One month in London is going to cost a lot more than one month in Bolivia.

If you’re trying to keep the budget down, it’s important to find the line between a country with a low cost of living that’s also safe and has fast, or at least usable, internet. If you’d like to know more about what the budget of a digital nomad looks like, check out my breakdowns for six months in Colombia, two months in Cusco, and one month in Mexico.

From one digital nomad to another, this long term travel FAQ will answer questions you didn’t even know you had! Understanding health insurance, budgeting, and what to pack while living on the road full time is definitely important to making a successful transition into a full time digital nomad.

Do you travel long term? Comment below with any tips and advice I missed! And if you’re just getting started in this lifestyle, feel free to message me with questions any time!

All my love,

Originally published at slightnorth.com on February 8, 2018.