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Thinking about ditching your office and hitting the open road?

This digital nomad lifestyle guide has everything you need to now to build a location independent lifestyle.

I’ve been traveling full time for more than two years now, and I’ve learned so much along the way. From packing tips to budgeting Q’s to accommodation advice and everything in between, my digital nomad lifestyle guide answers 10 commonly asked questions you need to know before you go. 


1. How long do digital nomads 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 five 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 a new city

We tried traveling on weekdays but with work it was just too annoying. Either trying to get stuff done on buses 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 of being stuck inside with work.

We stayed six months in Medellin and that was way too long. Then we spent 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.


2. How do digital nomads find short-term/furnished accommodation?

Good question! I 100% recommend Airbnb, and it’s all that I use.

It’s great because if you stay for a month or more hosts usually always offer a discount – sometimes up to 50% off. We rented outside of it once in a foreign country and it ended in disaster.

If you’re dead-set on staying off Airbnb (admittedly the prices are usually higher, but it’s a worthwhile trade 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.

Read More: How to Rent an Apartment in a Foreign Country.


3. How do taxes work as a digital nomad? 

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 didn’t 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 spending most of the year 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 or are making mad money.

But like I said, absolutely every situation is different and definitely look into your own job and finances. DO NOT take my word for it and definitely do your own research!


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4. What’s the best health insurance for the digital nomad lifestyle?

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.

Daniel 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 health insurance through 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.

Just like taxes, 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.


5. What do I need to pack for long term travel?

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.

Now, absolutely everything I own fits in my carry-on sized Osprey backpack. Check out my detailed packing list for long term travel to see exactly what I have in the bag, what resources I use, what subscriptions I pay for, and much more!


6. What are the best countries for the digital nomad lifestyle?

The awesome thing about the digital nomad lifestyle is that pretty much nowhere is off limits. These are the steps I usually take when deciding which countries to visit, and some things you definitely need to keep in mind.

First, look at flights.

Cheap flights are usually my deciding factor. I always compare prices on flights with Skyscanner, and search from the major airports around me 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.

Next, explore accommodation options

After you’ve narrowed down the countries that are affordable to get to, 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.

Third, check out the average cost of living

The next step is to check the cost of living in the options you’re looking at. 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.

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, double check your visa status

Double and triple check 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 of months ahead of time. Everything else like local transport and planning what to do waits until we arrive.


7. What are the best location independent jobs for digital nomads?

There are plenty of ways to make money while you travel.

If you want to work abroad you can teach in Dubai with very little qualifications, get a job working on a yacht, or become a flight attendant or an au pair. 

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 for step-by-step guides to all of these jobs and more. 


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8. Can digital nomads live in any timezone?

Timezones are the lamest.

For the first 14 months that we had our location independent jobs, we stayed in timezones close to the US in Colombia, Peru, and Mexico.

Now, we’re in Eastern Europe, which puts us six hours ahead of the US.

Daniel has a full-time job and is tied to the American nine to five… kind of. He has only one meeting every day and they do it at 10 am so he can take it at 4 pm. Besides that, sometimes he needs to answer an email or message later in the night but surprisingly it’s been very easy to still work normal hours even in a different timezone.

However, six hours really isn’t too much of a difference and I think Australia or Asia would be more difficult.

As a freelance digital marketer and writer, I have had clients in England, Singapore, the Philippines, and Australia. Working around their timezones hasn’t been too hard, 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.


9. What’s the best phone plan for the digital nomad lifestyle? 

I used to use the Sprint Open World plan but unfortunately, they discontinued it.

Now, Daniel and I use Google Fi and it’s awesome. Read my full write-up on the plan to see how much it costs, what you get, and why I think it’s the best international phone plan on the market today. 


10. Much much does the digital nomad lifestyle cost?!

This is one of the most common questions I get, and the answer is simple: The digital nomad lifestyle can cost as much or as little as you want.

It really depends on the cities and countries that you choose. One month in London is going to cost a lot more than one month in La Paz.

However, for a better idea of what the budget of a digital nomad looks like, check out my breakdowns for six months in Colombia, two months in Cusco, one month in Mexico, and one month in Romania. You’ll notice that it creeps up as the years pass and our income increases as well. 

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.


Bonus: 5 Pieces of Travel Gear Every Digital Nomad Needs

Before you hit the road, do it in style with my top five pieces of travel gear that I truly can’t live without after 2.5 years on the road! 

Osprey Packs Farpoint 55 Travel Backpack, Volcanic Grey, Medium/LargeOsprey Packs Farpoint 55 Travel Backpack, Volcanic Grey, Medium/Large

1. 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.


2. 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. The Vibrant bottle 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 Women's White LeDge MiD Ankle Boot,Dark Brown,8 M US

3. 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 this pair of Timberland boots. They were a bit 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.

Ultimate Ears BOOM 2 Phantom Wireless Mobile Bluetooth Speaker (Waterproof and Shockproof)Ultimate Ears BOOM 2 Phantom Wireless Mobile Bluetooth Speaker (Waterproof and Shockproof)

4. 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 UE Boom 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.


5. Vypr VPN

Simply put VPN’s can route your internet browsing through different countries so you can access websites with geographical restrictions. Before I started traveling, I thought every website was available to everyone in the world, but I was so wrong.

I use Vypr VPN to continue browsing the net just like I was in the US. It’s great because one membership allows you to install the VPN on three different devices and I’ve had no issues with my service so far.

If you’re interested, use this link to get 25% off the annual plan.

EDIT: I’m updating this to add that I also really love my Panda Planner to keep me organized and my new compression packing cubes that let me fit more in my bag! 


Build a Location Independent Life with the Digital Nomad Lifestyle Guide

These are ten of the most common questions I get from friends, family, and other travelers on the road, so I hope these answers will help you out as well. Let me know in the comments below if there’s anything else you want to know.

The digital nomad lifestyle isn’t to make happen, but it’s oh-so-worth-it! Good luck!

Ready to go? Use Skyscanner to find the cheapest flights to your next destination and then explore accommodation like unique stays on Airbnb or the top-rated hotels on to plan the perfect night, weekend, or long-term stay in the country.


This article is part of the Digital Nomad Series. Read the rest below:

9 Countries That Offer Long Term Visas for Digital Nomads

Ranked: Best & Worst Non-Schengen Countries for Digital Nomads

How to Convince Your Boss to Let You Work Remotely (in 7 Steps)

How Much Time Do Digital Nomads Spend in Each Place?

How Digital Nomads Make Friends When Traveling

The Complete Carry On Packing List for Long Term Travel 

How to Rent an Apartment in a Foreign Country 

Then, explore the complete Long Term Travel series for more insider tips on making the transition to a location independent lifestyle.


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