Why Flying to a Road Trip Might Be Your Family's Best Trip Yet

Contributed by kidfriendlystays

For a long time, I thought of "flying" trips and "road trip" adventures as two very different kinds of vacations. Booking a flight for my family meant packing light, traveling far and choosing the perfect accommodation. Road trips meant loading up the car, sticking within four-hour drive days and having the flexibility to bop among a few different places. It took me embarrassingly long to realize I didn't have to choose.

I’ve found some of our favorite family trips have been a hybrid: fly to our destination, rent a car, and let a whole region unfold instead of just one city.

The trick, it turns out, is twofold — finding the right route, and packing light enough to make the flight feel easy while bringing versatile travel gear that pulls double duty between planes and cars. That's where our Wayb Pico really shines: fitting easily in an overhead bin or as an FAA-approved child seat on an airplane, and again the moment we're buckling in for the drive. No gate-checking, no wrestling a bulky seat through security, no wondering about the safety what we're getting handed at the rental counter. It folds up, it flies with us, and it's installed within a few minutes before we're pulling out of the airport. 

Here are a few fly-then-drive routes for families worth adding to your list:

The Great Lakes Best-Kept Coastal Secret

Fly into Chicago, drive the West Michigan coast, fly out of Traverse City

This one might be my favorite road trips yet, and it’s rarely talked about by families outside of Michigan. Fly into Chicago, pick up a rental car, and drive north along the Lake Michigan shoreline through the charming coastal towns of New Buffalo, Saugatuck and Grand Haven, and visit the awe-inspiring Sleeping Bear Dunes before landing in Traverse City to fly home. The whole route hugs freshwater coastline that feels like the ocean without the salt or sharks. You’ll find dune climbs, lighthouse-adorned piers, cherry orchards, and beach after beach after beach. Expect bonfires and lots of ice cream stops.

*About 5-6 days, 350 miles.

Sedona Sunsets and Grand Canyon Views

Fly into Phoenix, loop through Sedona and the Grand Canyon

There's something about landing in the desert that resets everyone’s sense of scale — and feels entirely otherworldly. From Phoenix, it's a straight shot up to Sedona's red rocks, then on to the South Rim for the kind of hikes and views that ensure the screens won’t get a second glance. Loop back down through Flagstaff, swapping mountain pines for saguaros over the course of a single afternoon. It's one flight and one rental car for three completely different landscapes. 

*About 5-6 days, 450 miles round trip.

Where the Mountains Meet the Sea

Fly into Seattle, drive the Olympic Peninsula

Seattle gets you started with a city day or two — catch morning fish tosses at Pike Place, visit the aquarium, and ascend up the space needle — and then let the peninsula take over. An overnight in Port Angeles, Forks or Kalaloch (for the rainforest and coast), then loop back through Olympia to return to Seattle. You’ll see rainforest one day, mountain lookout the next, driftwood beach the day after that. It's a short enough loop that you’ll never feel like you’re living out of the car, but varied enough that your kids are likely to stop asking "are we there yet," because there keeps changing. 

*About 6-7 days, 400 miles round trip.

Lobster Rolls and Lighthouses

Fly into Boston, drive the coast of Maine, fly out of Bangor

This one is a straight shot up the coast rather than a loop, so you’re never backtracking over ground you’ve already covered. From Boston, pass through Ogunquit (stop to stroll the iconic Marginal Way) and drive up through Portland for lobster rolls at a picnic table by the water, then on to Camden, where the harbor is so postcard-perfect it barely feels real. From there it's a short hop to Bar Harbor and Acadia National Park, with Bangor's airport waiting less than an hour past that. Tide pools, lighthouses, and a whole lot of pine trees.

*About 5-6 days, 300 miles.

What I love about these trips is that they don't ask you to pick a version of a place. You get the airport ease of a direct flight and the wandering, in-between magic of a road trip, without spending half your vacation driving hundreds of miles just to connect two points. And when the car seat that flew with you clicks into the rental car in under a minute, that in-between part stops being the hard part of the trip. It just becomes part of the adventure.