Long-term travel planning: here’s how you should do it

When I first thought of the possibility of traveling long-term, I didn’t have anyone to tell me how to do it. Everything was based on individual research which will make your browser pop millions of tabs (reading long-term travel tips etc) so I thought, why is there not one article that will tell you everything you need to know?

Long-term travel planning is very stressful. It will make you anxious and in the middle of it, you might think of backing out.

It’s just too much information to handle at once. I struggled in this department but you don’t have to. You know I am obsessed with your long-term travel dreams, right?

This post will tell you all the essentials in long-term travel planning. I wanted to create a huge resource but I figured to have individual articles for it so that it will be easier for you to absorb. If you are not sure how to start, this one is for you!

#1: Deciding where to go

I am sure sometimes you sit down on your computer and find yourself spending hours on Pinterest. Why do I want to see so many places?!

I know it gets overwhelming sometimes but let me tell you that this is the only way to go = your goals and desires + your budgetCombining these two important factors will help you narrow down the long list you’ve been looking at for weeks.

When I plan for my long-term travels, the best trick I do is pick one country and then seeing their neighboring countries.

Choosing your long-term travel destination by region gives you a more realistic approach and a more doable style in long-term travel.

My 3 travel destination suggestions for long-term travel

#1: Southeast Asia

Southeast Asia is not only Southeast Asia is cheap but it is also a region thriving in tourism. This region is used to tourists and is very much welcoming to foreigners.

Cross-country buses are also available so it is safe to say that the transportation system is very efficient.

As an Asian, I felt safe when I first traveled Southeast Asia. There were not a lot of hardcore crimes but I’ve heard stories about Asia’s safety issues in terms of natural tragedies.

For example, three British women died after climbing a waterfall in Vietnam. As far as I know, this is a natural event that doesn’t have to do with any crimes or brutal attacks.

It’s okay to try all the extreme activities you want when you are already out there but make sure you will only do what you can. Always be extra careful!

For your route, start in Singapore. I don’t know where you are from but as a well-developed country, Singapore is the gateway to Southeast Asia.

With enough numbers of flights and operating airlines, Singapore is your easiest point of entry wherever you are flying from.

From Singapore, you can go to Malaysia by land. Go all the way up to Thailand, cross to Myanmar, jump to Laos, and then Cambodia.

Continue your journey to Vietnam. You can simply do all these countries by land border crossing (via bus or private vehicle).

Once you’re done with Vietnam, you do PhilippinesIndonesia, Brunei, and East Timor in random order as you need to fly to these countries. Land border crossing won’t be possible.

#2: Central America

The percentage of Americans traveling the world has increased and for them, Central America a perfect area to start because of its close proximity to the USA.

For people from the other side of the globe, it seems a bit unrealistic for first-time long-term travelers to start their journey in Central America – it’s too far!

With this boom, this region has learned to move around tourists and I promise you it won’t be hard. In fact, the countries in Central America are too small it makes it easier for land border crossing!

We talked about ‘natural disasters/calamities’ as a safety problem of Asia above but I will be honest with you about Central America: they’re a bit chaotic than normal.

Honduras has the highest crime rate in the world; the illegal US border crossing from Mexico is still happening. So far, that’s all I know.

However, I’ve visited all Central American countries and didn’t feel threatened at all.

For the route, literally do it as it is. If you start in the North: Mexico-Belize-Guatemala-El Salvador-Honduras-Nicaragua-Costa Rica-Panama.

Buses in Central America travel cross country so you will not have a hard time traveling overland.

#3: South America

South America has the same culture as Central America. Some people even do a one-time Central & South America trip because it’s so easy and accessible!

I traveled South America for 3.5 years and I never felt threatened. The worst case I heard while I was there was the murder of 2 Argentine girls in Ecuador.

It’s a shame that things like this can happen most especially to women but I have to say that I never had a bad experience while I was traveling South America.

Check out The Route: How to travel South America by land. It’s an extensive post I made and a good resource for long-term travel planning.

#2: Visas

The not-so-fun part of my long-term travel life: visas. I’ve had my fair share of struggles with visa applications that is why early next year, I vowed to myself to only travel visa-free countries for Filipinos.

Since then, everything has been easier for me but here are some ways on how I was able to survive:

  • Select a region where you are 60% visa-free. I chose South America because I can enter 7/13 visa-free countries.
  • In my experience, the Schengen visa can only be applied to your home country. For example, I was traveling to Northern Morocco in 2013 and wanted to cross to Spain, the consulate in Morocco did not let me apply for the visa because I am not a resident of Morocco. Even if I was granted a student visa to Milan in 2010, I can’t apply for a new visa unless I am in the Philippines. For me, going back is more expensive and doesn’t guarantee that I will get the visa so I have never gone to Europe since 2012.
  • Other countries will let you apply for a visa even if you are not in your home country. Only Europe is strict.
  • When applying for visas outside your home country, make sure to have all the files you need: birth certificate, bank certificate, proof of funds, travel insurance, etc. We will discuss all these later on.
  • If you have a valid US visa, you can enter the whole of Central America freely without applying for individual visas to Mexico, Guatemala, Costa Rica, Panama, etc.
  • When I entered Georgia, I didn’t know I need a visa prior to arrival. The Internet said I can apply for the visa at Tbilisi Airport but the airlines in Athens won’t let me board without the visa. Finally, when I arrived in Georgia, they saw that I have a 5-year valid visa to Japan so they let me in. How did that happen? Read more about the OECD agreement between countries. Apparently, you can enter other countries if you have a visa within the agreement.
  • When in doubt, always ask the nearest Embassy/Consulate near you. They can answer your questions better as it really varies. For example, the consulate of Argentina in Rio de Janeiro didn’t grant me an Argentine visa but in Montevideo, they did. Each consulate has its different rules and requirements so you better check it with them.
  • Don’t take no for an answer. Remember, the Schengen visa is the only visa that you can’t apply for outside your home country. Other than that, you can apply for a visa for any country everywhere. They will always say you can’t but be tenacious about it and say it’s possible. Because it really is.
  • Relax and answer all questions truthfully. You are traveling long-term and you don’t want to overstay in one country, right?
  • The consequences of overstaying in a country: you will be fined or worst, you will be banned. As a long-term traveler, you don’t want to have these records because they will cut your dream of traveling the world.
  • In the event that you fall in love with a place and decide to stay longer, I would understand. It happened to me when I first came to Tel Aviv. 8 months later, I am still here. I am not a resident here but what I do is still follow the normal tourist visa requirements. If I am granted 90 days, I have to leave. I can always go back. I’ve done it four times already since August 2016!

#3: Flights

Again, it all boils down to the region you chose to travel to. In my case, I only book flight tickets if I am to travel to another region.

For example, I was in Northern Africa in 2013 when I woke up and said, “I want to go to South America.” I booked the flight a week before and set off.

In my experience, the ticket goes to waste if I wanted to change my plans last minute. Remember that when you are traveling long-term, the possibility is endless, plans will always change and the timeline you made for yourself will always evolve into something different.

The Philippines is probably the only country that doesn’t allow its citizens to fly out without a return ticket. Due to the increasing cases of illegal Overseas Filipino Workers (OFWs), every time we go out, we all have to present a “proof of return” aka plane ticket back to the Philippines to make sure that we are really coming back.

I never had plans of overstaying in any country but as a Filipino citizen, I have to obey the rules. When I left for Africa, I knew I will not go back for a long time so I purchased a two-way ticket (Manila-Singapore-Manila) but only used MNL-SG.

I booked my ticket to Johannesburg from Singapore. Thankfully, the airline in SG did not ask me for a ticket going out of South Africa.

The Budget Airlines Theory

I did this a lot and I always ended up paying more. Remember that if you are traveling long-term, you have to check-in and for me, the luggage makes the bulk of the flight expense.

Some budget airlines will not tell you that check-in luggage is not included in your purchase and you will only find that out when you are already at the airport. It happened to me a lot and since then, I promised I will never book with low-cost airlines ever.

They are called budget airlines because they are individual flights from several airlines. Meaning, the flight booking platform will find the cheapest tickets in separate airlines and match them to your search. They are longer – it can take up to 30 hours for a $300 Europe-Asia ticket.

I know we always look at the price whenever we are booking but think about this: the most ideal (and not tiring) itinerary for you will always be expensive.

Sure, you booked a $240 Los Angeles-Manila flight but can you imagine how many stops that flight has? And in those stops, how many meals do you have to pay separately?

Big airlines always have meals included in the ticket price. It is also more comfortable – they have entertainment, they have blankets, eye covers, earplugs, socks, etc.

You are paying for that kind of service so don’t think about cheap. There is no such thing.

#4: Accommodations

When I started long-term travel, I had this rule that I will never be picky about accommodations but I will never be cheap on food.

Believe it or not, in 3.5 years of traveling in South America, I didn’t pay for any accommodations because I always found a way to get it for free.

This is how I was able to stretch my finances through free accommodations:


While you are still back home, try hosting Couchsurfers just to understand the dynamics. I hosted a lot when I wasn’t traveling yet and when I did, I realized I hosted so many people that they all wanted me to stay in their place to return the favor.

Imagine, in Buenos Aires, I stayed with three different people, moved every 4 days just because the people I hosted wanted to give back the hospitality. Couchsurfing is a good platform to meet friends and of course, sleep for free.


In exchange for free food and accommodation, I volunteered in hostels and bars. This method helped me a lot to improve my language skills.

4 bars and 3 hostels later, I am now fluent in Spanish. Plus, I get to work with fantastic people all over the globe who are also backpacking!

Workaway, HelpX, and WWOOFing are some great volunteering websites that will not only help you save money for your trip but also give you inspiring experiences.

Family Stay

If I am not volunteering, I am with local families where I get to learn about the culture and language of a certain country.

This also enabled me to know how they live their daily life and do the same. I’ve been a part of many Latin families in South America and I consider them my own.

House Sitting

It’s as simple as this: families go on a long vacation and they need/want someone to stay in their house. While they’re on vacation, you take care of the house.

Do whatever you want. Just don’t invite people over and do a house party. Basically, it’s like living in your own house. I used Trusted House-Sitters in searching for possible gigs.

But sometimes, I don’t want to work. Remember that all the items above will deprive you of having your alone time.

You have to talk or go out with your Couchsurfing host, do 5 hours of work when volunteering, participate in the local family stays, and watch for pets when house-sitting.

All these entail a certain level of social skills and let’s admit it: sometimes, we just want to be left alone.

#5: Travel insurance

Yes, you need it. You really really need it. I’ve ignored this for over 5 years of long-term travel but when shit went down, I realized it is really important.

We usually put this in the lowest priority list because we have this mindset that nothing will happen to us (which is good, btw).

Unfortunately, that’s not the case all the time. There will come a day that you will spend more if you don’t have travel insurance.

Travel insurance is an emergency ticket when something major happens. For example, you catch dengue fever while vacationing in Sri Lanka, this insurance will have you covered.

Though I am not from a country where health insurance is popular, I know the difference. Health insurance is what you have back home and serve the purpose of non-major things such as a personal visit to the doctor just because you feel like it.

Most people purchase one for this but it can also cover lost/stolen/damaged luggage, missed flights, travel delay, stolen gadgets – it really depends on the plan that you are planning to avail. The following are the most common package:

  • Global coverage of at least one million dollars ($1 million).
  • No deductible in case of hospitalization, a medical consultation, and obtaining prescription drugs.
  • Provisions, in case of medical repatriation or emergency medical evacuation, allow a 100% coverage of the actual costs for up to the global coverage sum.
  • In case of death abroad, expenses for the return of the body.
    A guarantee that your vehicle will be brought back to your residence.
  • Immediate relief of acute dental pain & emergency treatment as a result of an accidental blow to the face

Each travel insurance plan is different so you should check with the company you are signing up with. They can answer all your questions better.

Some tips on purchasing a travel insurance

  1. Buy yours in a real travel insurance company. It usually costs more from airlines or tour operators and more often won’t give the proper coverage you need.
  2. Make sure to get coverage that fits the type of traveler that you are. For example, Digital Nomads need to include their gadgets in their travel insurance. Choose something that you can maximize.
  3. Always include delayed/canceled flight coverage in your travel insurance.
  4. Stop saying “it’s too expensive. Nothing’s going to happen to me anyway.” You’ll never know what will happen to you on the road so you are not in the position to say that. Learn to include this list of things to do before traveling overseas. It’s not about the word “cheap.” It’s about YOU. Just get one! It’s for your own good.

#6: Vaccines

Remember when you were young, you were forced to take the pain from shtloads of needles because your mum said you need it?

Your mom is right. Traveling or not, you need vaccines. Fortunately, when I left for long-term travel, I already took everything. Here are the vaccinations you need:

Vaccines are also based on destinations so in any case, before leaving home, go see a doctor and ask about the necessary vaccines you will need.

I know that was a lot to digest but don’t freak out! There is no perfect formula for long-term travel but there is you. Remember that your will and enthusiasm, traveling or not, is more important than the money.

Should you quit your job to travel?

I didn’t quit my job to do long-term travel. It was actually accidental so I just made a living out of it. There is no judgment if you really want to leave your 9-5 because there will always be something for you out there. However, you have to consider other things.

I mean, let’s be honest – if you are to go on long-term travel, you really have to find another income stream. There is no way you can leave of absence for a year because if that’s possible, everyone will do it.

My friend Pamela is working in a multinational company in Singapore and she asked for a 3-month leave. It was approved.

I helped her craft the letters she needed to submit to her superior, encouraged her to try, and told her to be tenacious in asking for the leave. In the end, it got approved! Below are the articles of her journey:

If you are to quit your job, think about the possible jobs you can do while on the road. More often than not, people with really good-paying jobs won’t quit just like that because it’s so scary not to know what’s out there for you. You’ll figure something out, I swear!

The salary won’t be that high but when you are out there, you will do things you never thought you could because you want to survive. Survival is human nature. Don’t you ever think you’re going to be alone or left with nothing? Try first.

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