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How to Plan a Family Gap Year

How do I get started planning a Family Gap Year?

What can I do to keep our trip on budget and keep my kids safe and happy on the road?

If anyone we know can help travelers plan a family gap year, it’s Jenn Miller. She’s been traveling full-time with her family for going on 8 years. Read on for her best advice on how to plan long-term family travel.

Planning an extended trip with a family can feel daunting. It’s scary enough to think of taking off for months to years as a single person, with only yourself to look after. The anxiety, the responsibility, and the planning are exponential when you’re doing it as a family.

When we took off for (what we thought would be) one year of traveling with our kids, we’d been planning hard for two solid years. We had checklists by week, for two full years. I kept a binder in my kitchen in which I documented everything, from gear research to routes, to insurance options, to educational questions and concerns, to resources that might be of use later. I read everything I could get my hands on; there weren’t thousands of travel blogs then, so mostly that meant books. We saved. We organized. We made contingency plans. We did our best to make sure that there would be no unexpected surprises that endangered our kids or pulled the rug out from under us financially.

If you’re in that place now, planning a big trip with your kids, let me assure you that the planning was both totally necessary and completely overkill. It was necessary because it was what helped us develop the nerve to take the leap. There’s no better antidote to fear than education and no better answer to the myriad of “what ifs” than the evidence that others have done it, so you can too.
It was overkill because it’s truly impossible to plan for a life you know nothing about, first-hand. We planned for everything, except the things we couldn’t have dreamt up (like the markets crashing 9 months into our journey) and those were the things that kicked our butts and tested our mettle.

For families in the planning stages, these are the top five considerations.

1.Get Your Finances in Order

This is the big one. How you’re going to make the money you have stretch, generate more, and avoid financial calamity upon your return bear thinking about seriously and organizing up front.

We saved for our first year and banked more than we thought we’d need. Then, like everyone else, we lost it all in the market crash while we were camped on the Adriatic coast of Italy. That was demoralizing. Necessity, however, is the mother of invention, and that crash ended up being the catalyst for the creativity that resulted in developing freelance careers that allow us to live and work anywhere. One year turned into more than eight. We’re still going.


  • Split your money among not less than three banks.
  • Carry redundant credit cards (we have seven or so that are back ups to the back ups).
  • Don’t touch your retirement fund.
  • Always carry a thousand US dollars “just in case” (there will be cases).
  • Take travelers’ checks–they might seem old school, but they’ve saved us on multiple occasions.
  • Think about ways to make money as you go to stretch your savings.
  • Work out your budget with generous margins, then add a full 25% to the total.

2. Plan Your Route

plan your RTW route with your kids

All of the “fly by the seat of your pants” style travel of blogdom fame sounds romantic, but trust me when I tell you that with kids, a little forethought as to comfort and efficiency goes a heck of a long way. There is no need to plan every night of your journey before you leave home, but having a general idea of where you’ll be when, perhaps pre-booking your round the world ticket and certainly making reservations for the first night in a new place at a decent hotel will serve you well.

How do you plan a route?

  • Consider your bucket list.
  • Take into account your kids’ dreams and interests.
  • Factor in weather.
  • Figure out where you absolutely must visit in high season.
  • Remember that you’ll save money in low or shoulder seasons.
  • Consider the educational potential and implications.
  • Weigh the time and money you have with the must-sees.

For example, we started in London because the museums there would provide an overview of much of what we planned to see later in our travels. Also, we figured beginning in a place where we all spoke the language would ease transitions to the new lifestyle. Add to that, the flights to London were cheapest from east coast USA, which is where we were living when we launched. Then, we traveled with the decent weather, since we were on bicycles. We planned to stay put for several months in the winter to be warm and relax a bit.

As we actually traveled, we modified that route to fit our daily realities, the recommendations of other travelers we met, and our own interests as they grew and changed.

3. Pack Less

Please hear me when I tell you that less is more, especially when you’re packing for kids. If you can possibly wrap your head around it, I highly recommend traveling in carry on bags only. Don’t check a bunch of stuff that you then have to wrangle everywhere you go.

If you can simplify to the point of one bag on each back, the joy in your journey will grow immensely. I can tell you with confidence that the greatest frustration of any trip I’ve ever taken with children, has been wrestling the baggage.

Packing Tips:

  • Three outfits per person is plenty.
  • Layers are your friend.
  • One pair of shoes, on your feet, is all you need.
  • Put some thought into your gear for multi-tasking and durability.
  • Make a hard and fast “carry your own stuff” rule.
  • Everything you need can be purchased anywhere there are people.
  • Reevaluate your needs vs. wants equation.
  • When you’ve packed as little as you think is reasonable, take out one more thing.

4. Assess The Risks

Fear is the big one that holds families back from travel. The world’s a scary place if the news is to be believed. In reality, the world is safer than it’s ever been. As parents, however, we have a responsibility to make sure our kids grow up healthy and safe, whether we choose to stay home or travel.

I’m not a fearful person, but I’m constantly in risk assessment mode where my kids are concerned. I’ve let my 15-year-old travel alone for a month (not on a tour, actually alone) to Guatemala because he was ready. I’ve let my 14-year-old backpack with a group of other teens on her own because she had the necessary skills. I’ve let my 17-year-old cross the Med and Atlantic under sail without me because it was a bucket list dream. I believe that the world is a safe place to raise kids to do adventurous things. That said, there are risks, and we can minimize them greatly with a little research and forethought.

Make travel safer:

  • Consider destinations carefully. Syria in 2017? Not so much. Russia? Go for it.
  • Make data-driven decisions. Do your research. On everything.
  • Invest in travel insurance, for health, gear, and emergency evacuation too.
  • Get the appropriate immunizations.
  • Carry the necessary safety gear for your adventure.
  • Use the same good judgment abroad that you would at home.
  • Take classes: first aid, CPR, and self-defense at minimum.
  • Join the STEP program.
  • Put together a legit health kit and pack it.

In general, any risk to your health and safety while traveling can be minimized through research and up front preparation.

5. Make the Kids Part of the Process

make kids part of the planning for RTW travel

Perhaps the most important thing you can do is to include your kids, regardless of their ages, in the planning. My kids were ten and under when we were working towards our launch. We had maps on the kitchen table and sticker countdown charts on the fridge. Weekends were filled with micro adventures carefully designed to build their stamina and skill set. We played games. We made it fun. We read stories and watched films. We brought the world home before we took them out into it.

Older kids may have real concerns of their own, about their stuff, their friends, their schooling and their routines. Remember that they only know the life you’ve given them and change is scary sometimes. Talking lots, involving them in the planning, giving them real responsibility in preparing for the trip can all help get a reluctant child on board.

Prepare Your Kids to Travel by:

  • Learning together about your destinations.
  • Planning as a family.
  • Playing games to make learning new things fun.
  • Practicing the skills you’ll need on the road.
  • Taking smaller adventures that build up to the bigger one.
  • Learning a language.
  • Talking, a lot, about how everyone is feeling.
  • Creating a safe space for both adventure and anxiety.
  • Creating community by connecting with other traveling families before you go.
  • Designing their educational component around the exciting adventures.

Remember why you’re doing this: To spend time and make memories together as your children grow. Don’t let the logistics of getting a project of this magnitude off the ground overwhelm you. Just take one bite at a time until you’ve broken the whole down into manageable chunks. Just like the journey will be made up of individual days, the planning can be accomplished one step at a time. Enroll in the RTW 30 Family edition for a 30 day intensive boot camp that covers every single aspect of planning a big time family adventure. You’ll come away inspired and equipped.

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