A Conversation with The Bucket List Family — TripIt Blog

Going Places is a new series from TripIt that highlights frequent travelers to showcase their unique travel styles and insider tips. 

In 2015, Jessica and Garrett Gee sold all of their belongings to afford a four-month trip with their two children. Fast-forward to 2022, the Gees—and their now three kids—are the well-known traveling tribe, The Bucket List Family. You might already follow them on Instagram, watch their YouTube videos, or have seen them on Good Morning America

But if you haven’t heard of them, here’s what to know: They’re an adventure-loving family that documents their trips around the world—and inspires millions of fans along the way.

Fewer things, richer experiences 

Life wasn’t always a flurry of planning travel and creating content for The Bucket List Family.

“If you told me 10 years ago that traveling would be my career—that I would travel to 90 countries with my husband and kids—I never would have believed you,” Jessica told me. “I wasn’t always a big traveler or explorer. But I’ve fallen in love with exploring the world with my family. I love living with less, and gathering experiences over things.” 

Experiences that they not only get to share as a family, but that they’ll be talking about for years to come. 

“One of our most memorable travel moments from this year was with the gray whales in Baja Mexico,” shared Jessica. “We charted a little boat at this place called Guerrero Negro. For decades, the gray whales have brought their calves to greet the local fishing boats. The whales love to be touched and scratched. We had a special mother and calf come up and the mother held the calf up to our boat for minutes so we could rub it. It’s an experience none of us will forget.” 

These unforgettable moments were a big part of why Jessica and Garrett embarked on this journey in the first place. “We decided as a young family that we wanted to take the time to create traditions that will hopefully shape us into better people the rest of our lives.”

“We understand how unique and amazing this opportunity is to take on the adventures of life together as family,” Jessica said. “We remind ourselves of this daily, and remember that it all started by making the decision to step outside our comfort zones, step way outside the norms of society, and follow our hearts for what we felt would be the best path for our family.”

So, where to next for The Bucket List Family? “Next on our bucket list is swimming with orcas in Norway and then seeing polar bears in the Arctic,” she said. “A lot of our travels are geared around wildlife!” 

On staying organized—and packing a positive attitude

Wildlife? Yes. Wild traveling life? Not a chance. 

“I’m always very well prepared for our travel days,” Jessica said. “When I pack, everything has its place.” 

And when it comes to organizing reservations (and more) for a family of five? “I use TripIt for every scheduled part of our trips: flights, rental cars, hotel confirmations—everything. I love that TripIt finds my confirmations automatically in my email and then adds it into my itinerary.” 

According to Jessica, feeling organized—and calm—goes a long way when you’re traveling with littles ones. 

“My best tip for traveling with children is to remember that, as a parent, you set the tone for the trip. If you’re stressed out on a travel day, your kids will feed off of that energy. You can’t always control what happens when you travel; things will go wrong. Your best choice is to press forward and have a good attitude.”

Tip: Travel plans not going according to plan? TripIt can help—whether it’s finding an alternate flight or claiming compensation for a delay or cancellation. 

Any final advice for families planning their next trip? “Just enjoy the journey! And relish the small things, like a good breakfast buffet, an airport with healthy food options, or an empty row on a plane!” 

After all, it’s the little things—nay, experiences—that make the journey worth it.

Catch up on all Going Places features to learn new travel tips, discover underrated destinations, and more.

About the Author

Amanda Wowk

Amanda Wowk is a freelance writer, founder of Amanda Wowk Creative — a content writing services company — and avid traveler. Her experience spans the travel industry, supporting clientele in travel tech, luxury travel, and consumer brands. When she’s not helping clients tell their stories, Amanda writes about her own experiences to inspire others to travel as far, wide and frequently as possible.


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