How to plan a family gap year

Where do you even start to plan a family gap year? School, work, travel, lodging, your current home, airline tickets…the list can be seemingly endless.

When we started, we had no idea how to plan a family gap year. It seemed insane in some ways to even attempt this…especially with a then 9, 6 and 4 year old.

After a lot of reading, a number of generous bloggers, and some tenacity, we completed our trip prep and left in June of 2023. Everyone is different but below is how we planned our family gap year.

Enjoy and happy dreaming and travels!

Our home- what did we do with our house?

The most daunting aspect to plan a family gap year for us was our housing in NC. We love our house and neighborhood and wanted to make sure the house was well-taken care of while we were gone. We were incredibly lucky when a friend had a good family friend that was relocating to North Carolina. The stars aligned for us (and hopefully for them too!) when we rented our house for 11 months to them. We’re so grateful that our house will be well loved and full while we’re gone.

Lodging on the road

Our plan for the family gap year was to use hotels for short stays and apartments for longer stays. We were originally using with their 10% back rewards program. However, recently rolled out a new combined rewards program that provides 2% cash back. This is a great incremental benefit for VRBO bookings but obviously a substantial devaluation in the future rewards.

As a result, we’ve been booking incremental stays, both weekends as well as longer, on Using the two travel cards below, we typically receive ~5% cash back, which adds up! We’re also booking all (or at least almost all) of these as refundable for when things inevitably change. The Europe portion of our Family Gap Year is action packed and we’re intentionally planning on slowing down in Asia.

Our cars

We had two Toyota Highlanders before this trip. All jokes aside, they worked great for us and were perfect for all the kids’ activities throughout the year. We decided to sell the older one and temporarily relocate the more recent one to my’ parents. We thought about selling both but decided to keep one for our return.


With a family of five, it would be easy to go broke buying plane tickets. When I was working at a company, we prioritized time and convenience, like most of our friends. We were willing to pay a premium for flights at the busiest times of the year because we were tied to the usual school/work schedule. However, we’ve since learned a lot about flights through different blogs and books. By far the most influential was Take More Vacations by Scott Keyes (Keyes is the founder of Going, formerly Scott’s Cheap Flights).

The lightbulb moment from Scott was to travel when and where the cheap flights occur. Let me explain. A typical trip used to start with us picking a location and dates. We would then use a tool like Google Flights to find the cheapest flights on those dates.

Now, we start by looking at flights to anywhere in the world during a certain month. This change in flight planning has made us realize how cheap it can be to fly.

The most practical example is that we were previously conditioned to think of a one-way Europe ticket as costing ~$500. You can imagine our surprise when we used the technique above and booked one-way tickets to Oslo for $193/ticket.

We also just booked flights for October from Milan to Bangkok for just under $400/ticket.


For those of you in the US, we think you’ll agree that the costs of the US healthcare system are a disaster. One of the biggest questions with forging our own path was around the cost and delivery of US healthcare. How do you plan a family gap year with this potentially enormous cost?

For a high deductible health plan (HDHP) without an employer subsidy, the quote we received was ~$18k/year for a family of five. That plan essentially operates as a catastrophic plan after the first $10k+ of out of pocket expense. Knock on wood, our family is healthy and it seemed like there had to be a better way.

Long story short, we ended up opting for Sedera, a medical cost sharing plan. It functions similarly to a HDHP but provides coverage in a catastrophic scenario (our main medical fear is the capital C word). The major benefit for travel is that this plan works outside of the US so if we receive medical treatment outside of the US, we’ll cash pay for it and then get reimbursed for any medical event exceeding $5k. For an annual cost of ~$4,700, this allows us to not only receive more efficient medical care but also build up a self-insurance base, to contribute to the inevitable large medical expenses one day (hopefully many years from now).

We read a number of well-written posts on healthcare but a special H/T to the posts from Mr. Money Mustache and Physician on Fire.

First aid class

It’s been a long time since either of us took our CPR classes as high school life guards. It goes without saying that almost everything in these classes falls in the unthinkable category but given we’ll be moving around, we want to be prepared and have peace of mind.

We looked at a variety of different classes and ultimately settled on Survival Med’s Online Wilderness First Aid class. The main appeal was that it covered not only CPR and the Heimlich maneuver but also how to prepare for a variety of common injuries in an environment far away from traditional medical year. It’s particularly well done because the instructor, Dr. Natalie Bonthius, is not only an avid outdoorswoman but also an ER doc. We highly recommend her course for any trip like this and it has the benefit of being online so you can complete it at your own time. We’re almost to the end but got sidetracked learning how to blog.


Everyone is tired of hearing about vaccines after the COVID saga of the past three years. But, one of the big topics for a multicontinental trip is of course vaccines. Despite the failures during COVID, we relied on the CDC, along with the help of our primary care doc, to determine what we needed. After an exhaustive review, we’ve settled on typhoid fever, Japanese encephalitis, rabies and a malaria treatment. We thought the list of vaccines was the hard part but it turns out buying these in the US is mindblowingly expensive. After calling seven places, we learned that the total for five people would be ~$16k…what?!?

There had to be a better way and fortunately we found World Travel Family’s post on vaccines. Besides discovering the price in the US is even higher than her experience, she aptly captures the anxiety of getting the prices. More importantly, that’s how we found the Thai Travel Clinic. We’ve read about medical tourism before but never thought about it in the context of vaccines. Ultimately, the vaccines are coming from well known vaccine manufacturers but aren’t being sold as luxury products. So, we’ve booked an appointment at the Thai Travel Clinic for our first stop in Asia in October.


There are so many terrible things that came during the darkness of COVID. However, like all things in life, each situation has both pros and cons. One of the great positives that came out of COVID was that Kate homeschooled our oldest child, Goose, during first grade. Homeschooling was daunting at the time but with the help of some friends and Singapore Math, it worked out very well. Fast forward to our trip and homeschooling is what we’re currently using to keep up with school, with the confidence from Kate having already done this once.


One of the great positives from the trip prep is that we’ve largely digitized our life. We’ve moved as much as possible online and used this as an excuse to unsubscribe from physical (mostly junk) mail. But, we still need to ensure we receive mail without being a burden to the family staying in our house.

We looked at a variety of mail services and ultimately settled on iPostal1. We’re going with the $99/year plan and that comes with a physical address as well as 30 scans/month (excluding junk mail). There’s an app to easily see the scans and although we’re hoping to not receive any physical mail that we need to response to, this will at least give us a way to say in touch with our mail and then revert back to physical when we return.

USPS offers mail forwarding up to six months, with an ability to extend for an additional six months. So, when we get close to 6/30, we’ll set up our iPostal1 account and then the USPS mail forwarding.


We’re currently using Mint mobile, recently acquired by T-mobile. It’s intuitive, cheap and just works. At $20/month per phone, it’s hard to beat in the US. The problem is when we started looking at all of these random countries and the availability/cost for a year’s worth of travel.

After six months of travel, we’ve learned that Wi-Fi is fairly ubiquitous so we mostly just keep our phones in airplane mode and use Mint’s Wi-Fi calling and text, WhatsApp for messaging and calling, and FaceTime for staying in touch with family. So far it has worked surprisingly well and we haven’t needed much incremental data. In Europe, we relied on wifi and had Mint UpRoam for emergency situations.

However, after arriving in Indonesia, we realized we’d need data more regularly since we primarily use Grab in SE Asia. As a result, we bought an eSIM on the street. It was cheaper and had more data but we quickly realized it would be a pain to set this up in every country.

As a result, we’ve started using Airalo for data. We tried the one month plan in New Zealand, which worked great. Upon returning to Singapore, we signed up for the Asia regional eSIM, which allows us to travel throughout countries in the region. It’s cheap enough and much more convenient for when we need data.


This topic seems mundane for planning a family gap year but given how expensive foreign transaction (FX) fees can be, it’s a key part of any long-term travel plan. So far, we are using credit cards as much as possible, primarily because of the ease plus the safety of not having much physical cash. In the US, our main credit card is Citi’s Double Cash, which offers 2% cash back on total spend. We have several other cards that have higher cash back returns on other categories and will write a full post on our credit card strategy, both in the US and for our Family Gap Year. But, Citi charges a 3% FX fee, which would add up if that’s our primary card a year.

Both the Capital One SavorOne card and the Amazon prime card don’t charge FX fees so these will be our primary cards. We’re mainly using the SavorOne card, which works out great because it has 3% cash back on both groceries and restaurants, our primary spending categories on the road. Combined with the 5% cash back that it provides for reservations, it adds up to a meaningful amount.


It’s easy to forget the benefits of being an American when we’re constantly bombarded with negative press. If you need a reminder, just check out the visa requirements by country. Americans can largely move freely throughout the world with few exceptions. That is an incredible, and easy to forget, privilege.

The first visa requirement that is going to impact us is the Schengen visa in Europe. As Americans’, we can stay in the Schengen region for 90 days within a 180 day period. After that, we’ll need to be away for three months before returning to the Schengen area.

The other visa that’s going to impact us is the Indonesia visa. This one is trickier because it’s only 30 days. But, there is an ability to renew once for an additional 30 days. Because of the complexities of this one, we’re planning on leaving just before the 30 day mark.

Otherwise, we’re mostly planning on moving around freely…thank you, Uncle Sam!

Passports – adults and kids

Top of the list on how to plan a family gap year is having valid passports for all five of us, including expiration dates later than six months after our expected return. Given that a child’s passport is only good for five years, we ended up having to “renew” one of our kid’s passports. There’s actually no such thing as a renewal for a child’s passport so that means booking an appointment at a passport center and creating a new application. We started the process in February and received Bingo’s passport in May, one month before moving out of our house.

International Driving Permit

It’s unclear if you actually need an International Driving Permit (IDP). From our reading, most sites suggest getting one for extended travel although many of the rental companies don’t require it. We didn’t want to find ourselves in an awkward situation with foreign police officers so we opted to get an IDP. IDPs are only valid for a year so we got this in July, while still in the US. However, the start date for our IDP is mid-August, providing more than a year of international driving ability. We got the IDP from our local AAA branch, which ran $20/permit. For more detail, check out the IDP page from The Points Guy.

International sailing certification

This is somewhat unique to us but one thing on our list to plan a family gap year was a bareboat sailing trip. We have been taking sailing lessons during the last three years and wanted to put these skills to work.

Many places in the Caribbean don’t require licensing but Europe has a very strict licensing requirement. Europe requires an International Competency Certificate (ICC) in order to bareboat. Ultimately, we looked at a variety of different locations and decided on Croatia for our multiday bareboat charter. The problem is the ICC isn’t issued in the US.

Fortunately, the American Sailing Association (ASA) issues a similar certification called the International Proficiency Certificate (IPC). The IPC can then be used at different charter bases in Europe for bareboating. If you go the IPC route, check with the local charter base to confirm the IPC is sufficient. The IPC is $49/skipper and the requirements include the first three ASA courses: 101, 103, and 104. After completing 104 in April, we submitted the IPC paperwork and received our IPCs just before we started our family gap year.

Learn more about our family gap year itinerary