It’s not every day you get to travel the world with your family in tow. But for Michael and Chelsy Gilroy of Maine, it was — for five months. Having worked in the international travel industry for many years, they had long dreamed of taking a big trip with their daughters, ages 11 and 13. A short, family trip to South Africa in 2014 was all the motivation they needed to begin planning a larger globe trot, and in December of 2018 they embarked on a epic journey, spanning from Hawaii to Scotland, with stops in Australia, New Zealand, Singapore, South Africa, Botswana, Namibia, France and Spain in-between.

For many families, even a weekend trip to the local amusement park can be a tiresome task, so it’s hard to believe pulling off a five-month, worldwide trip. Still, with some planning, there are many ways to make long-distance traveling with kids easier, according to Michael and Chelsy.

Plan in Advance

When it comes to international travel, there’s a lot to
consider: shots, visas, informing state departments, booking flights, arranging
lodging, passports, birth certificates and more. But consider a five-month
period with kids, and there are significantly more layers of planning.

Two years before taking off, Chelsy was already conversing
with her daughters’ teachers about the best time of the year to pull them out
of school and how to handle home schooling on the road.

Tap Your Network and Have
a Purpose

Many families have traveled internationally and come back
with lessons to share. The Gilroys sought them out.

“We had two other really good friends who did the same thing
with kids of similar ages,” Chelsy said. “They sort of paved the way with the
advice they offered.”

In addition to learning from other families near home, the
Gilroys reached out to friends living in the countries they planned to visit.
These local relationships and visits during their trip helped them learn about
local cultures and preserved a sense of safety while traveling.

They also contacted trusted organizations and affinity
groups that they had connections with to plan learning opportunities during
their trip. “If you don’t have an existing connection, reach out to them in
advance and create a relationship,” Chelsy said.  

While it can be tough to plan a trip to multiple
destinations, having a purpose for each location can make it easier. For
example, the Gilroy family shared a passion for animals and the outdoors — two
things that largely dictated the travel itinerary.

“I think some people, when they plan trips, think they’re
going to educate their kids, so it’s Europe, it’s the history, it’s the culture,
and the churches and the old buildings. Those places are remarkable, but we
were so drawn to the outside world,” Chelsy said.

Those passions ultimately led to nights sleeping under the
stars, afternoons running barefoot down massive sand dunes in the Namibian
desert, learning about the preservation of rhinos with Save the Rhino Trust, watching
a hippo from mokoros (wooden canoes) in Botswana, traveling along the Garden
Route and swimming with penguins in South Africa, hiking, rafting and learning
about endangered kiwi birds in New Zealand, and much more.  

Unplug and Leave
Urgency Behind

“I think the biggest takeaway from this whole trip, by far, really
wasn’t so much a cute moment that happened as much as just this ability to
suddenly have your life distilled down to a backpack and the people you love
the most,” Michael said.

Everyday life is jam-packed with distractions, from devices
to work obligations to traffic. While traveling is not necessarily free of
those things, traveling the world with your family means paring down to only
the necessities and one another’s company.

It wasn’t until three months into the trip that the Gilroys
truly felt that they didn’t have to go everywhere and see everything. The glory
of a months-long trip is the ability to relax and not feel the sense of urgency
that’s often felt on a shorter trip.  

“The fact that we had five months really allowed us to enter
into this experience without a sense of urgency, which really changed the sort
of calculus and how our day unfolded,” Michael said.

The Bag Matters and
Less Is More

“A soft bag with wheels,” Michael said, in regard to
traveling necessities. “The key is having something really sturdy that can
actually roll.”

Plus, he said, when traveling with kids, make sure they can
handle their luggage themselves — or else you’ll get caught carrying four bags
everywhere.

At a certain point in the trip, the Gilroys only cared to
dig so far into their bags. “Top layer living,” they said. They recommend
considering the weather where you’re going and to remember that a heavy pack
quickly becomes a drag.

“We scaled our packing down as we started traveling more,”
Michael said. “For four and a half months of our trip, we were either in the
southern hemisphere or some…