21 Secrets I Wish Someone Had Told Me About Long Term Travel


Long term travel is a lifestyle that more and more people are choosing because of the freedom and adventure it provides.  For anyone planning long-term travel, I’ll share the secrets and tips I wish someone had told me before I set out on the road.  

There are many things to consider before embarking on this journey. You need to make sure that you have adequately budgeted for long term travel, you have enough savings or a reliable source of income from a remote job, and you know which countries will be welcoming to your visa type and passport.  If you are still in the planning stages make sure to bookmark my long term travel planning checklist and timeline.

But beyond the basics there are some secrets that you only learn once you are on the road.  Traveling long term will be one of your best life decisions and you’ll learn plenty of lessons along the way.  Luckily you can learn from my experiences and mistakes before you sell or put all of your stuff in storage, ask your boss to work remotely, and set out for your adventure.

Here are my best tips and secrets to help you make the transition more manageable and less stressful, indulge your wanderlust, and live the long term travel lifestyle to the fullest.  

1. You’re probably going to take way too much stuff.  Be strategic with your belongings.

You might think you won’t be able to find your favorite toiletries but bringing several months’ supply is unnecessary.  Unless you are going to be in a very rural area, you shouldn’t worry about finding what you need.  Most major brands distribute worldwide.  Not only will you likely find every major brand but you might find local products that become your new favorites.

On the other hand, make sure you have plenty of your medications to last your trip.  Talk to your doctor about generic alternatives if you need to get refills while abroad.  

You’ll also take way too many clothes and end up only using half of what you pack.  This might be because you don’t judge the climate accurately or because most people use a more limited wardrobe than they think.  

Limiting your toiletries and clothes will decrease your baggage needs and save you money on baggage fees.  This is especially important if you are a digital nomad or traveling to multiple locations.  Plus, the fewer suitcases you take, the less you risk the airlines losing your luggage in transit.  

2. Research your tax situation and obligations ahead of time.

Not researching taxes ahead of time can result in unpleasant surprises.  If you will be earning money and paying taxes in another country, make sure to research any Double Taxation Treaties your home country has with your new host country.  You might find that you will be bringing home a lot less of your hard-earned paycheck.

You’ll also want to figure out if the length of time you will be living in another country will make you a tax resident there and require local tax payments.  If you are a digital nomad, consider applying for a digital nomad visa with tax benefits.

As a US citizen, you are obligated to file taxes with the IRS no matter where in the world you are living.  A good place to start learning about taxes when living abroad is Deskless Nomad’s tax guide for digital nomads.

Taxes are complicated and can be hard to figure out on your own, especially the first year you are abroad.  Find an accountant at home or in your host country who knows what they are doing so you can plan ahead of time.    

3. Consider buying a used van and converting it for camping and exploration.

Outfitting a used van into a campervan was one of the best decisions I made when traveling in New Zealand for a year.  We built a platform bed that converted to a sitting area, bought a roll-up futon mattress, made curtains, and strung up little lights.  

We used this vehicle to explore the far reaches of New Zealand’s north and south islands.  Even when we weren’t camping, the van was still a perfect place to relax and have lunch after a hike or other adventure.  

With a little elbow grease, you can turn any van into an adventure mobile.  You might even be able to find a van that someone else has already converted.  At the end of your stay, you can then sell the van to recoup some, if not all, of your money.

4. A foldable or inflatable kayak or stand-up paddleboard is a must in countries with large lakes or coastal areas.  A bicycle is a great way to explore certain destinations.

One of my best decisions when moving abroad was buying a kayak.  Depending on your skill level you can paddle coastal areas, rivers, and lakes.  Paddling offers a completely different experience than hiking when exploring an area.

Secondhand kayaks and stand-up paddle boards can be hard to find abroad, especially folding or inflatable ones that travel easily.  If you are traveling to a country with lots of beaches, islands, rivers, or lakes to explore, consider purchasing a kayak or stand-up paddleboard to bring with you.  It will transform your experience.

A bicycle is a great way to explore your new city, neighborhood, local trails, or country roads.  Many countries, especially in Europe, are very bike friendly.  You can easily find a second-hand bike through online marketplaces or classifieds after you arrive in your host country.

5. Consider bringing camping gear for long treks in wild places.

Hiking is one of many ways you can be a more eco-friendly traveler. Some places have multi-day hikes with huts where you can spend the night but still need a sleeping bag or bedding.  Other places have huts with full bedding and meals provided.  In many places, you will need a tent if you want to camp while exploring the backcountry or long trails.

Research your planned adventures ahead of time to determine if you will need camping gear for long hikes in wild places.  Camping gear can be quite expensive in some countries, especially if it is imported, so investigate how much it might cost to bring equipment with you.  You might also look for local organizations or shops where you can rent or borrow gear if you don’t plan to use it that often.

6. Leave your American ways of interacting at home.

I say this in the kindest way possible.  Not every culture interacts with strangers in the way Americans do.  Other cultures don’t smile nearly as much.  Approaching someone with a big smile and a loud, friendly attitude will immediately label you as American.  

Learn to watch how locals greet each other and interact.  Mimic them to blend in and put strangers at ease.  Once people get to know you then you can let that American smile shine.

7. Tipping is not expected and is even discouraged in some places.  Even when and how you pay the bill may differ.

The American practice of tipping can be very confusing for foreigners who visit the US.  Likewise, you may find yourself confused by the tipping (or non-tipping) customs of your host country.  

How and when the bill is brought to patrons of a cafe or restaurant also varies by country.  In some places, it is considered rude for the waiter to bring a bill before you ask for it.  In other countries, you are expected to go up to the register when you have finished eating to review your bill and pay.

Read up on local customs ahead of time so you don’t find yourself in awkward situations.

8. The weather will likely be different than you expect. 

With climate change, the places you visit may experience more weather extremes than historic patterns.  The weather will undoubtedly vary from what you are used to or are expecting.  

Be prepared for all kinds of weather.  Even countries on the equator may have higher elevations with snow.  Plus you never know when you’ll get the opportunity to take an unexpected side trip to a colder (or warmer) destination.

9. New environments can mean new illnesses.  Talk to your doctor about ways to stay healthy when traveling.

It is reasonable to expect that tropical climates and developing countries are more likely to have illnesses you have not previously been exposed to like malaria, hepatitis A, yellow fever, typhoid, Zika, Chikungunya, measles, and tuberculosis.  Even developed countries will carry different strains of common bacteria and viruses that are more likely to make you sick.  

Get your travel vaccinations completed before you leave.  Wash your hands before eating.  Avoid peeled or unwashed raw fruits and vegetables.  Consider wearing a face mask on public transportation if covid or flu is prevalent in the area. Learn about other ways to stay healthy and travel safely.

10. You might be surprised to find you feel safer than being in the United States.  Or you might find that you feel unprotected.

Many countries are far safer than the US.  Strangers in other places are often kinder too.  

On the flip side, your rights when traveling abroad can be weaker than they are in the US as a US citizen or resident.  Be aware of local laws and avoid any sketchy situations.  You don’t want to get arrested in another country and have to navigate a foreign legal system.

11. The best use of an extended stay in a destination is to use it as a base to explore nearby countries.

Wherever you make your new home, position yourself in a convenient base to explore a region.  Choose accommodations with easy access to a major bus station, train station, or airport.  

If you are a digital nomad, staying in a base country and taking multiple smaller trips to explore may make more sense than moving around to different cities or countries.  Take advantage of a digital nomad visa that allows you to stay up to 1-2 years in a country where you can easily make trips to surrounding countries.  Digital nomad visas have their pros and cons but can come with some great tax benefits.

Sign up for email notifications on price drops for flights and train trips.  Make a list of must-do getaways but be open to random trip suggestions.  Explore beyond your local area.  

12. Consider setting up an account with a local bank if you will be in one place long term.

If you are staying in one place for an extended period, consider setting up an account with a local bank.  Apply for a local bank debit card.  You can sometimes apply for an account online and transfer funds prior to ever arriving in a country.  

Having a local bank account will make it easier to transfer money to your new landlord for rent payments or to pay bills back home.  Renting an Airbnb long-term and using the platform to pay rent with a credit card can be a way around needing a local bank for rent payments.  Just be sure to educate yourself on how to avoid Airbnb and short-term rental scams.

You could also consider signing up for an online international bank like Revolut that allows you to easily access or transfer your money anywhere.

13. Taking your pet on long-term trips can be challenging but so worth it.

Taking your pet abroad is a complicated decision.  You’ll have to weigh how long you will be gone with the cost of transport and inherent safety risks of travel.  But for those who will be gone long term and consider their pets family members there is often no other option.  

Start learning about the process early since it can require up to 6 months of tests, vet exams, and certifications depending on your destination country. 

If you plan on staying in Airbnbs, read my Complete Guide to Bringing Your Dog or Other Pet to an Airbnb.

14. Look at all of your visa options. It can be easier than you think to get a work visa for skilled workers or a digital nomad visa for remote workers.

Some countries make it very easy for skilled workers to get work visas, even without a sponsoring employer.  Depending on your situation and if you are not planning to work, a long tourist visa may be your best choice.  

If you are self-employed or a remote worker, you now have even more options with digital nomad and remote worker visas.  Check out Digital Nomad’s Complete Index of Digital Nomad Visas.  

Check your passport to make sure it won’t expire while you are abroad.  Some countries require a passport to be valid for at least six months at the time of border entry.

15. The same job or occupation in another country may be very different from what you do in your home country.

If you take a job abroad with a role similar to what you do in your home country, be prepared that the job may vary from what you are used to.  

Expectations about work ethic, working hours, holidays, accountability, and supervision may surprise you.  There is a reason many consider American work culture to be toxic when compared to other countries.

16. Your living environment while traveling long-term can greatly affect your mental health so choose your housing wisely.

The comfort and general ambiance of your accommodations may have a profound effect on your mood and daily enjoyment of life.  Even if you are only staying for a month, choose a place that feels good.  

Look for rentals with plenty of sunlight, less ambient noise from the street or neighbors, kitchens that are comfortable to cook in, and some sort of outdoor space to get sun and fresh air.  Digital nomad villages and co-living spaces are great options when traveling and working remotely.

Choose a neighborhood with lots of activities you enjoy to encourage you to explore the area, get out and meet new people, improve your mental health and help prevent loneliness.  

17. You can make new friends ahead of time to jump-start the feeling of home.

Making new friends ahead of time can make the transition to a new home abroad so much easier.  There are also plenty of ways to make friends or meet other digital nomads while traveling.  

Consider attending a digital nomad conference in the region or joining a local Facebook group to start interacting with your future neighbors.  You can choose local special interests or hobby groups or ex-pat groups to find future friends.

18. Birthdays and holidays can be hard during long-term travel.

Birthdays and holidays can be tough when you are a long-term traveler or digital nomad but new friends can make them extra special.  Many ex-pat communities recognize this challenge and make a special effort to be inclusive around the holidays.  Consider organizing a gathering for other travelers you meet to celebrate their birthdays.

19. You may get robbed, scammed, or just lose your valuables.

Foreigners are easy targets for pickpockets and scammers.  Getting robbed or scammed is an unfortunate part of traveling and is all too common.  Read up on safety tips and travel scams to prepare yourself.  Get a money belt, store digital photos of your passport and other important documents online, and have an emergency plan.

20. Constantly speaking in another language is exhausting.

While language classes can be a fun way to travel and make friends it is challenging to get to the skill level you need to have easy casual conversations.  Having to communicate in another language all of the time can take its toll.  

Learn how to use google translate on your phone since this can be a lifesaver, especially if you find yourself in an emergency situation.

21. Long-term travel insurance is an absolute necessity.

I would never consider traveling now without long-term travel insurance.  Whether it’s loss of luggage, illness, or accident, travel insurance will have you covered for life’s unwelcome surprises.


Final thoughts

I hope my secrets and harsh truths about long-term travel will help you as you prepare for your own adventures.  Long-term travel is exhilarating and can fulfill a lifelong dream but it’s best to know what you are getting into.  There are many pros and cons to the digital nomad lifestyle. Whether you choose the long-term lifestyle for a gap year or a lifetime, you’ll never regret what you learned and how you grew.

If you liked this article and want to learn more about preparing for long-term travel, check out my checklist and timeline for planning long-term travel.

Jamie Dubois

I am a freelance writer, wanderer, kayaker, rock climber, and adventurer exploring the world on my own terms.

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