How to Plan a Gap Year Traveling With Your Kids

Two expert families on how to make your world travel dream a reality.

It’s easy to get caught up in the routine of life when you’re raising kids. School, homework, chores, ferrying your little ones between soccer practice and violin lessons. All that nagging, menu planning and grocery shopping can be exhausting. During your downtime, maybe you find yourself endlessly scrolling Instagram, dreaming about far off beaches and those gorgeous jewel-toned towns hugging the Amalfi Coast.

The good news is this: your dream can be turned into reality. Plenty of families are leaving their homes and living out of suitcases. Some go for a few months, some a year, others make travel a new way of life.

Chelsea and Matt Gillespie of Unsettled Down and their 2-year-old daughter Kailen have been traveling full-time for over a year, and summed it up like this: “Happiness is when everything you own fits on your back and every everything you love fits in your arms.”

Whatever your vision, traveling families are here to help. Here’s top advice and tips to turning your life on its head and taking your kids on a trip they’ll never forget.

What To Do With Your House

One big concern people have when taking an extended vacation is dealing with their house. Theresa Stevens of Epic Round The World Trip and her family, who live in Marin County, Calif., took their gap year trip as a major excuse to purge their stuff. Once they’d cleaned out their house, they rented it.

“We also lent many items to the people who rented our house and to friends who could use them while we were gone,” she said. “It was just so liberating to live out of just one suitcase per person and now we’re aiming to live much more lightly once we’re back home.”

Another idea is to do a home swap, where you trade houses with another family for the duration you’re gone.

The Gillespies chose to get rid of most of their stuff since they’d be traveling permanently, but keep a car in New York so they have transportation when they fly back to the U.S. for a visit.

How to Budget for Full-Time Travel

travel budget — There are a lot of ways to cut down your budget, like choosing cheaper destinations and eating on the cheap.

There’s one good way to think about budgeting for a gap year, says Stevens: “Plan to spend what you would spend total on everything in a year at home. Then, add a 15 percent contingency on that for unexpected overruns. You may spend a lot less than this, but it’s a good starting point for planning purposes.”

She said there are a lot of ways to cut down your budget, like choosing cheaper destinations and eating on the cheap.

“Europe, Australia and New Zealand are very expensive,” said Stevens. “Various parts of Asia and South America can be inexpensive. In Bolivia, for example, we could get a delicious and filling three-course meal for $4 per person.”

Travel Slow, Stay Longer

The Gillespies have one major tip when it comes to budgeting for travel: try out slow travel, where you stay in one place for a longer timeframe.

“We usually avoid renting a car if we can and find a home base near city center,” said Chelsea. “We also find that discounts are provided for week-long or one-month rentals. For example, we paid $780 in Dubrovnik for a large two-bedroom with a view of the ocean by renting for four weeks during the shoulder season. We also love slow travel because you can truly immerse yourself in that city’s culture and live like locals instead of just vigorously checking off bucket list items."

She said: "We get to enjoy and 'live' in the place we’re actually visiting. We save a lot of money by going to the local grocery stores and renting flats with spacious and adequate kitchens.”

Keeping Your Finances In Order Back Home

home finances — When traveling the world, life back home keeps on happening.

Even when you’re having the time of your life traveling the world, life back home keeps on happening. When mean those bills keep on happening, too.

Stevens said they did a lot to prepare for their one year foray abroad, including:

- Set up a travel checking account and kept it separate from everything else, so that if it got compromised while traveling, they wouldn’t have access to other funds; kept only enough in that to cover upcoming bills and “fed” it from other checking/savings accounts

- Went paperless wherever possible

- Set up automatic payment in full for all credit cards and other bills and tracked bank balances to make sure they’d cover bills by payment dates

- Gave a trusted relative power-of-attorney in case of emergency

- Had mail forwarded to that person who let us know of any items that needed attention

- Downloaded transactions from all accounts and categorized them to track spending vs. budget as we went. We used an elaborate spreadsheet we created, but there are online tools as well. This was important, so that we could be comfortable splurging at times and pulling back at other times to make up for it.

Choosing an Awesome Itinerary

passport — With so many countries to go to, choosing can be a challenge.

With so many gorgeous countries out there, choosing where to go can feel like one huge case of analysis paralysis. But, you have to start somewhere.

“Start with your wish list of fantasy destinations and then prioritize, with an emphasis on safety and what your kids can handle,” said Stevens, whose family traveled to 21 countries on their year-long trip. “We aimed to maximize good weather and to travel in one direction. We then created a big-picture plan by continent — X months on this continent, Y months on that continent, to catch the seasons at the right time.”

Since the Gillespies are a full-time traveling family, they approach their itinerary in a different way.

They don’t plan further than eight weeks in advance, and are constantly abiding by the Schengen Rule, which allows you to stay in the contiguous border countries of Europe for 90-days at a time without a visa. After those 90 days, you have to go somewhere else. “We personally call this the Schengen shuffle,” said Chelsea.

The Down and Dirty on Homeschooling

travel school — The kind of schooling kids get while traveling is of huge value.

Theresa Stevens puts it like this: “I’d say spend a summer trying to homeschool when there are a million other things all of you would rather be out doing. If it goes well, great, if not, then 'road school,' and let them catch up when you get back.”

Stevens, who has two pre-teen daughters, said it’s good to let the kids know there will be some form of catching up after the trip. You should be aware all the schooling they’ll get while traveling is of huge value to your kids.

The Gillespie’s daughter is only 2, but they already know this about her schooling: “Ultimately, we want to teach our child that not all classrooms have walls. She won’t learn empathy, heartbreak, or joy from textbooks or backlit screens. She’ll learn from experiences and be better for it. Travel will spark her character, open her mind, and strengthen her courage. It will teach her more than we ever could alone.”

How to Deal With Health Insurance

Health insurance is a nightmare at home, so how could it be any better when you’re gallivanting around the globe?

The Gillespies have three forms of travel insurance: traditional employment medical coverage, travel insurance through Allianz, and coverage on their travel credit card.

“A lot of people think our lifestyle is risky, but in all honesty, we work hard to ensure we always have a backup plan and we’re not putting ourselves in a bind,” said Chelsea.

The Stevens family had domestic insurance, plus travel insurance for one year.

“We kept domestic insurance to cover the possibility of a catastrophic medical event that would force us to come home early for treatment," Theresa said. "Then we also had travel coverage through GeoBlue Voyager, in case something happened overseas (which would likely not be covered by domestic insurance). Do read your credit card fine print for any medical evacuation or other coverage they may provide, but there are conditions attached.”

World Travel Isn’t Always What You See on Instagram

If you’re preparing for your trip, you’re probably following a bunch of traveling families to try to catch an iota of an idea what it’s like traveling with kids. The problem with this: those social media feeds won’t teach you a thing.

When traveling abroad, it’s important to be flexible and understand things won’t always go as planned.

“In the first few months on the road, we discovered the good, bad, and ugly sides of full-time travel. It may seem like all fun and games on our Instagram, but our life isn’t only filtered photos,” said Matt Gillespie. “Most of our time outside parenting and work isn’t sightseeing. It’s hundreds of hours researching, continuously outlining itineraries, planning transition days, and budgeting. Without constant attentiveness, we wouldn’t survive a week. We learned that bit the hard way.”

Mishaps are always going to happen when traveling, and it’s important not to take them too seriously. Just recover and move on.

Theresa remembers being separated from her daughters in Vatican City, and had to get on the phone with security to find them.

“There are many things that can happen, so you just create contingency plans to make them as painless as possible. Assume any of it can happen, visualize it, and be ready with a plan. That prevents panic when it actually does happen,” she said.

Keeping Kids Involved When Traveling

kids travel — It’s important to keep your kids involved with travel plans, especially if they’re older.

It’s important to keep your kids involved with travel plans, especially if they’re older. Stevens said her kids had fun adding to the fantasy destination list.

Then their oldest daughter started making YouTube videos of their travels, and the younger daughter did research on destinations and educated the family.

“Some kids will enjoy tracking the budget or even planning some of the logistics,” said Stevens. “Ours had fun helping search for apartments in various destinations and deciding on what activities we would do on any given day or leg of the trip.”

'Home' Is Where You Are

postcards — Find ways to give kids a sense of ownership over travel plans.

Even though the Gillespie’s daughter is only 2, she also “helps."

“We put our daughter in a new bed every few weeks," said Chelsea. "We live out of backpacks. But on Day 11 of our nomadic life, Kailen used the word 'home' to describe our new flat. The bed in her room became her 'owl-bed' because of the paintings above her mattress. She now gets excited about every new room she resides in and names them on her own.”

Her daughter also loves looking through pictures of homes they can rent or cities they want to visit, and she learns new words about those places all the time.

“We teach her new words like 'Duomo' or 'piazza' to help her get excited about the things she is going to see,” said Chelsea.

The Best Ways To Get Around?

How you choose to get around during your worldwide adventures largely depends on your family. The Gillespies' hands-down favorite form of transportation is the train.

“It’s inexpensive and an easy way to transport all of our stuff. Our last train ride was seven hours but there was also a ‘family car’ where all the kids gathered to watch a movie and play together in a designated area,” said Chelsea. “Flying is such a hassle, so we avoid it when we can. Hiring a car can get really expensive, especially in certain countries.”

The Stevens family said they had a variety of favorites.

“Add boats and live animals, such as horses, to the list as well!,” said Theresa. “We did them all and had the best experiences with planes and rental cars.”