7 Practical Things to Consider When Planning a Gap Year

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As we find ourselves on the final lap in preparation for our family gap year, I wanted to share some of the main considerations we have had to work through. Once we shove off, I will write a follow up post on what we wished we had considered. But for now, it is enough to know that we have been busy beavers for the past two years slowly but steadily lining up our ducks.

For more in-depth coverage of this topic, I’ll refer you to our book recommendations. My top recommendation for practical planning advice is Choose Life: The Tools, Tricks, and Hacks of Long-Term Family Travellers, Worldschoolers and Digital Nomads by Daniel Prince.

Here is the list of things to consider with links in case you wish to skip to the topic you’re most interested in:

  1. How will you afford it?
  2. Will you keep a home base?
  3. How do you plan to travel?
  4. What are the social needs of each family member?
  5. How will you explain yourself?
  6. What about schooling?
  7. How will you keep your family healthy and safe?

1 – How will you afford it?

This was probably biggest question on your mind, right? A year (or more) of non-stop vacation sounds nice, but how are you going to pay for it?

Fear not. There are several ways to tackle this concern. Most likely you’ll be able to combine several of them to enable you to financially support yourself and your family for an extended period of time abroad. And no, you don’t need to generate gobs of passive income, though if you can somehow manage that, let me in on your secret.

That said, possible and easy are two different things. I’m not going to claim that this will be easy for everyone. When we are financially able to go, it will be because we really wanted it to happen. We will have worked, schemed, experimented, and spent wisely to get there.

Strategy 1: Minimize Costs While Travelling

I travelled to Mexico and volunteered at a summer camp in construction. I made my humble home in this barn on premise and paid exactly $0 for my three month stay there.

The key here is that long-term travel can and should be much cheaper than your annual two-week trip. Therefore, we need not extrapolate the $6,000 dollars you spent on that one week in Orlando and conclude that a a year-long vacation must then cost 52 x 6K, or $312,000! No, that’s not how it works.

How much will it cost then? I must give that most frustrating answer: it depends. It depends on how fast you plan to move locations, how big your family is, what luxuries you can’t live without and, well, how much you spend. From my research somewhere between $45K and $65K USD (or about $4K to $5K a month) seems to be a reasonable ballpark figure.

The three most significant expenses for long-term travel will be transportation, lodging, and food. In light of this, one strategy to minimize all three major expenses is to stay in a place longer. As a result, you will use less transportation, get cheaper pricing on a place to stay and, if so inclined, cook your own meals at least part of the time.

Another factor is where you travel. Cost of living in the countries we most want to travel to in South America and East Asia is very low.

Furthermore, you can minimize costs by taking on WorkAway stints, volunteering as I once did in Mexico (3 months, zero lodging costs), house sitting, or home swapping. More on this in the “How do you plan to travel?” section.

Strategy 2: Save Money

Some people do it with nothing but savings. We plan to save enough for a year, plus enough to tide us over when we come back. But our hope is to also make enough money that we can minimize the amount we need to draw down our savings, since we might just want to keep going after the year is up!

How easy it is to accumulate enough savings to travel long-term obviously depends on your income and current expenses. If saving $50K seems impossible, combining some savings with some form of income is another way to go.

Strategy 3: Make money from anywhere.

Unless you’re a millionaire, you can’t draw down savings forever. So you will want to consider how you can continue to make money on the road. This is especially the case if you think you may want to extend your travels indefinitely.

As tragic and as soul-numbing as the COVID pandemic was, one silver lining for would-be digital nomads was that digital nomadism became kind of normal. A lot of people worked from home; the world did not come to an end. Some even worked from foreign countries because, why not? Remote work technology took a big leap forward and now even your most technophobic colleagues can video conference. Of course it depends on your profession and your employer, but keeping your job and working remote might be a viable option for you.

My wife, Liuan is a freelance writer and author, so she can just carry on with her career. I’m a software developer working for an engineering company, so it’s possible I may work part time as well. Or maybe I’ll try to freelance. We’ll see.

Another way we plan to make some additional income is by renting a single-family home I purchased and fixed up a year ago. This may not be your cup of tea (the place I bought smelled like sewage and was infested with German cockroaches), but I enjoy that kind of work.

We all have that thing that most others don’t like to do, that is our niche. What is your talent and how can you offer it to the world from anywhere?

Strategy 4: Find the Freebies

Many people use credit card points and other travel hacks to save money however they can. You can also reduce costs by knowing how to look for cheaper flights – my go to site is skyscanner.com, which if you’re flexible with your dates can get you some killer deals.

I used to think the time of booking or searching for flights incognito made a difference, but apparently not.

I’ll confess, credit card points are not my thing. However, we have some friends who are quite savvy on this topic and have pointed us in the right direction several times. By applying for the right credit cards, they pay for most of their flights with points and get additional perks like airport lounge access. They offer their advice and services on their blog.

Also, research bank accounts that offer free or reimbursed ATM fees internationally (those stinking fees add up) or that provide better currency exchange rates.

Strategy 5: Sell everything.

Many world travelers opt to sell everything. They sell their house and belongings to turbocharge their travel fund. Additionally, they eliminate the expense and headache of having to store, maintain and pay bills.

Our family has decided we are not ready to leave our current life behind for good. But, you never know, we could always change our minds later.

Strategy 6: Convert your home into a vacation rental.

For us, the “sell everything” approach feels too permanent (and scary). To tell you the truth, we really like our neighborhood and we like our home that we fixed up ourselves.

That’s why when some friends of ours suggested we put our home up on AirBnB we realized that was the perfect solution for us and we got to work getting our home ready for listing. As a proof of concept, we rented out our home several times while we were away on small trips and the experience was nothing but positive. We brought in plenty of money for our efforts, people left the place orderly and clean, and we had no trouble getting it booked (except in January).

You may be thinking to yourself, well that’s great for you, but my home isn’t anywhere someone would want to travel to. Well guess what, neither is ours. Many of our visitors come to visit family or have something to do with the college a few neighborhoods over. There really aren’t any hotels near our neighborhood, and our place fits more people (i.e. a family with kids) and is more pleasant than a hotel room.

2 – Will you keep a home base?

If you plan to sell it all and skip town, you can take a pass on this section. However, if you’re like us and aren’t ready to burn your bridges you’ll have to consider how you will maintain that home base while your gone. This will likely consume a lot of your planning bandwidth because there is a lot of details to work out.

The Cost of a Home Base

If you’ve owned a house for any length of time, you know that it doesn’t just sit there quietly waiting for your return. Pipes corrode. Roofs leak. Squirrels get in the attic. The little smidge of mold in the corner of your shower spreads. The city sends citations for the hayfield that used to be your beautifully manicured front lawn.

Cars don’t sit idle very well either.

That means your biggest headache is going to be figuring out how to have all this stuff used (respectfully) and cared for while you’re not there. Where will your mail go? How will you pay bills? Who will cut your grass and weed your garden?

Once while visiting Colombia for just two weeks a polar vortex descended upon our home region. Our first reaction was to smugly feign concern for our shivering friends back home while we sipped our passion fruit smoothies. Our follow up to that was desperately trying to send out a plea for help through Facebook over crappy WiFi after remembering that we had turned down the heat to conserve energy and our pipes were in danger of freezing.

Then of course, there is the cost of utilities (i.e. heat so your pipes don’t freeze), property taxes, maintenance, and most likely a mortgage.

Leveraging your Home Base

Despite all that, keeping your home has it’s advantages. You might have friends or a school district you really like. You might have put a lot of work customizing your house and have fallen in love with it. Those are all certainly true for us.

So why not turn your property into an advantage? You can do this by setting it up as a short or long term rental. That way, your home is making money and paying for itself, if not adding to your travel funds. With the proceeds you can hire someone you trust to manage it and coordinate cleaning and yard work. As a bonus, any issue that comes up, say a roof leak, will be addressed right away.

If you are not leaving for your long term travel right away, you can test the concept by listing it on AirBnB or VRBO when you go on your mini-vacations or weekend getaways.

Another piece of advice: if you aren’t leaving immediately, keep a log of any home maintenance items as you do them. This will help you budget and coordinate those activities when you ultimately end up entrusting to someone else’s capable hands.

3 – How do you plan to travel?

There are many ways to travel long term. With this in mind, it may be worth your time researching what’s out there. Different modes of travel offer different advantages, experiences and budgets.

Will you fly somewhere and then hit the road in a car or a converted van? Or will you stay in one place for several months and decide where to go next when you’re ready to leave?

There are many ways to travel in a way that minimizes (or eliminates) housing expenses. You could volunteer or do work assignments through a site like workaway.info. Or you could go woofing. Some stay for free wherever they go by home swapping. Others participate in house sitting – basically live in someone’s house for free and in return, cutting the grass, feeding the fish and walking the dog.

You may also want to consider ways to minimize your carbon footprint and support eco-tourism while you travel. My wife will be researching this during our gap your, so more on that to come.

The questions you should be asking yourself and your family are:

  • What do we want to learn and experience?
  • Can we reduce expenses through the way we travel?
  • Is it possible we might want to travel for longer than we initially thought?
  • How much interaction do we want with other travelers? What will our social lives look like?
  • Can we travel in a way the respects local communities and does as little harm to the environment as possible?

4 – What are the social needs of each family member?

It may be hard to predict how people will react to life on the road, but it’s worth thinking about. Some of us will be perfectly satisfied to spend our days alone or with our immediate family. I tend to be one of those. Others, like my wife and my oldest son, may need to mix things up and socialize or play with others.

While it might seem like there couldn’t possibly be more than a handful of families doing this type of thing in the world, you’d be surprised that there are whole expat and nomadic communities all over the place. Friends of ours that traveled for year participated in a world schooling community in Indonesia and had a great experience. Just a bit of Googling will reveal all kinds of traveling communities out there, and chances are there is one out there for you.

Also, keep in mind that wherever you go there will be locals that you can befriend. This may be more or less difficult depending on the community, but we plan to do this whenever possible. Look out for opportunities to participate in the life of the community. That’s part of what you wanted to experience in the first place, right?

Traveling, of course, means that friends made now will result in tearful goodbyes later. This shouldn’t discourage you from making friendships. But acknowledging and anticipating the differing needs of your loved ones and how they may react with this new way of life could help soften future misunderstandings and mitigate homesickness.

5 – How will you explain yourself?

I know what you’re saying to yourself, “I don’t give a rip what people think, I’ll just do it.” I know, me too. Unfortunately, though, you can’t just fake your own death and disappear. You will have to tell someone.

And here’s the twist, many of them are going to take a negative view of what you’re doing. After all, it makes sense, you are a part of their life and your choice to leave is taking something from them.

Also, people tend to interpret the choice to do life differently as an implicit criticism of their own way of life. Whether or not you mean it that way, they might feel judged. And the default reaction to being judged is to judge back. Therefore, expect some sharp questioning salted with accusation.

That’s why, when you approach your friends, your mom, your boss, your nanny, your pastor, your therapist and whomever else, it might be useful to have thought out a calm and coherent answer to some of the most common questions asked. I personally don’t have an answer to every question, and that’s ok. In fact, if you’re like me, you might prefer to play it by ear and let chance take it’s course. But others want to know:

Won’t the kids get behind in school?

How can you leave a stable job like that? How will you support yourself?

Won’t the kids miss their friends?

I thought you were concerned about global warming, how is jet-setting going to help?

Aren’t you putting your family in danger in [insert country with low cost of living]?

Note how I worded those questions. That’s probably how they will be asked. Just keep in mind you’ve already mulled this over and concluded that everything will probably work out. Your friends have not had a chance to do this. So giving honest and clear answers is a better approach than getting defensive.

6 – What about schooling?

There are essentially four options I’m aware of for educating your child while traveling long term or taking a gap year. I honestly don’t yet know which one will suit us in the end. Nevertheless, here they are:

Enroll in Local Schools

Yes, this is actually an option. Obviously, for this to be viable, you’ll need to stay put for more than a few weeks. But the advantage is language immersion and making friends in the local community.

Formal Homeschooling

Get a formal curriculum and teach it to your kids. The advantage here is you are maintaining continuity with their “home” education track and they are more or less learning what their friends are at home. Another advantage might be that you don’t have to create a curriculum from scratch if that’s not your thing.

I’ve even heard of cases where the home school district will agree to provide curriculum and other support. This can be to the benefit of the school if they are able to count that as partial enrollment for funding purposes.

Informal Homeschooling

Piece together a curriculum while ensuring that they don’t get behind in “core” subjects like literacy and math. Of course, your whole adventure is going to be an education worth more than some pictures in a textbook. So consider that tour of the Terracotta Army in Xian or that jungle wildlife tour your history or biology lesson for the day. This is probably the approach our family is leaning towards.


Don’t force any curriculum on the kid. Just help her learn about whatever she’s interested in at the moment. While I find this approach intriguing, I will admit to being more than a little nervous about completely trusting my kid’s intuition about what they need to learn. Nevertheless, the concept to be rooted in the science on the ways we actually learn. So maybe that’s just a prejudice I need to unlearn.

7 – How will you keep your family healthy and safe?

Along with the question of finances this is one of the biggest questions to consider. Furthermore, it can feel more outside of our control than finances. At least with our savings account we have a simple number to measure how prepared we are.

With long term travel, especially with kids, it is easy to slip into the fear that you’re just inviting tragedy. But in my travel experiences, I’ve had mishaps and misadventures, but I’ve never been in any serious physical danger. This of course is no guarantee that it can’t happen. Much of it depends on where you go, what precautions you take, and a bit of chance and luck. But even at home, there are risks.

The suggestions I provide below are not an exhaustive list of how to stay safe and healthy. Furthermore, there are different predominant risks in different countries and common ways to avoid them. With that in mind, you should do your research on the place you intend to travel. These are just a few general recommendations we have learned from experience or from others.

Get travel insurance for long term travel.

We plan to get travel insurance when we take our gap year. We typically don’t get special insurance for shorter trips because your regular health insurance and even your credit card will often cover you. But for long-term travel it is definitely worth having this. I found this post very helpful and plan to refer to it again when it comes time to buy a plan for our gap year.

Split up your money and important documents.

Once when I was in my early twenties travelling alone in Mexico, I got pick-pocketed on an overnight bus ride. As a result, I woke up in the morning with no money or passport. To rub salt in the wound, I had no cell signal. While I obviously survived, but it was no fun and never want that to happen again.

That’s why I always make sure I have a backup stash of money and copies of all my documents stored separately from my main stash. If anything should happen I can rely on the backup. Before I traveled with family, I would sew secret compartments in my underwear or stuff cash and a debit card in my shoe.

Now that I always travel with family I need not suffer the chafe of hard plastic. There is always at least one more adult in our group. We make sure all adults have a stash, usually stored in different ways (in a bag, on our person, back in the room, etc.).

Learn as much of the language as you can.

This might seem an odd one to put under health and safety, but this has gotten us out of a pinch so often that it seems worth including.

Not a natural at languages? No problem. You need not be anywhere near fluent to say “I have a problem”, and utter a few words of context like “lost” or “where is x”. Learning even a small amount of the language greatly increases the chances of you finding the help you need quickly.

Put yourself in a local’s shoes. Imagine someone walks up to you panicked and speaking Russian. Assuming you don’t know Russian, you are not going to know how to help and will likely feel a little panicky yourself. So pick up that Duolingo app and see how far you get before your next trip.

Identify your local allies.

The safest and easiest way to travel is to travel with a friends or family that are local to the region. We do this when we travel to China (my wife’s family is native to China). We have done some independent travel in China and it is a very different experience.

That said, it’s not reasonable to expect that you’ll have friends and family everywhere you want to go.

So the next best thing is to figure out who your local allies are. When we travelled to Indonesia, we found that the homestay staff would do just about anything for us. We learned to rely on them to set up our transportation and other matters. Likewise, when we had an instance where are driver didn’t show up and we didn’t know what to do, we found a coffee shop, bought some drinks, and found that the owner was happy to help us call our host and get things sorted out.

Before being helped by the coffee shop staff, a group of scammers found us. They can smell hapless tourist scent for miles. They tried to get us to ride with them for four times the price after feigning a call to our host and not getting an answer.

That leads me to the corollary of “identify your local allies”, which is, “identify the scammers”. As a rule of thumb, someone who approaches you – especially while you and your family are looking lost standing in the middle of the path with your luggage strewn around your feet – and offers you anything more than no-strings-attached advice, don’t take them up on it. Don’t follow them. Don’t get in the car. And don’t accept their services.

If it feels wrong, don’t do it.

Sometimes you just get a bad feeling about a situation. Don’t just push through and do it anyway.

Rules of thumb can’t anticipate every situation. But fortunately our brains are wired to apply our past experiences to the current situation and detect when some ingredient seems rotten, even when our conscious brain can’t point to what’s off. This is called intuition.

When traveling in a group, take care not to succumb to peer pressure and override the lone voice of reason. Everyone draws from different experiences and might catch what others miss.

Make a plan ahead of time for what-ifs like getting split up.

I first heard about this idea on a great podcast covering the topic of travel safety and I definitely plan to use this advice whenever we travel. The idea is to come up with worst case scenarios and then practice responding to them with role play. For example, what should a child do if he gets separated from the group? In that case, maybe you identify a tall landmark whenever there is the risk of getting separated where everyone can regroup.

Don’t be a hero.

If you do find yourself in physical danger, for example a mugging, let’s just agree right now that you will hand over the dough. You are not the Mandalorian and you are at grave risk of real physical harm or worse. You are worth more to your kids and spouse than your cash or your cellphone, so hand it over and deal with the inconvenience later.


It wasn’t my intention to end this post with “don’t get mugged”. So I’ll attempt to end on a sunnier note.

I’ll reiterate here that it is our experience and the experience of many other traveling families that long-term travel around the world is safe and doable – even for regular middle-class families. If this is something you want to do, don’t let anyone tell you you can’t. It’s your life.

For some, all this planning and plotting might seem a bit overkill. In my younger days, I probably would have thought the same and just improvised as I went. There’s nothing wrong with that. But at this time of my life there’s just more I care to preserve on the home front. So if you find yourself in that situation as well, hopefully this helped.

I am aware that this post doesn’t cover every detail. It might not even cover every main idea. But hopefully it at least gave you a framework and some leads to start doing your own research and planning. In the future, I’ll flesh out each of these main topics on their own, in which case I will update this article with links.

In the meantime, if you think I overlooked any main considerations, I invite you to let me know in the comments.

  • Matt

    Matt is a software consultant by day and a wide ranging hobbyist at night. He enjoys baking, art, music and lives for travel experiences. But what gets him out of bed in the morning is fresh roasted coffee.


Matt is a software consultant by day and a wide ranging hobbyist at night. He enjoys baking, art, music and lives for travel experiences. But what gets him out of bed in the morning is fresh roasted coffee.

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