house with deck in woods in The Hamptons

The journey is nearly as great as the destination: your vacation home. (Photo: Marriott International)

Road Trips

The Great Getaway: Drive the Long Way to Your Perfect Home Away from Home

It’s been said that travel is as much about the journey as it is the destination. If that’s the case, and the final stop on your travels is an extraordinary vacation home rental, map the ideal road trip route to your house — or use your abode as a base from which to explore.

We’ve sourced some of the most stunning vacation home locales along with the most unforgettable road trips to get you there.

Cape Cod

Leave mainland Massachusetts and drive over the Bourne Bridge toward Cape Cod’s windswept shores and salty sea breezes, stopping to explore this bent-elbow-shaped cape’s charming towns, beaches and ubiquitous clam and “lobstah” shacks. Drive 6A for a respite from busy highways and cruise past cranberry bogs, former sea captains’ homes and salt marshes.

cape cod beach
Explore the Cape Cod coast. (Photo: Getty Images)

Get a taste of New England’s seafaring spirit in Falmouth, walking or peddling the Shining Sea Bikeway through town and past the coast. Then learn about the Cape’s glass-blowing tradition at the Sandwich Glass Museum.

Imagine life as a successful sea captain at Yarmouth’s 1840 Greek Revival Captain Bangs Hallet House, get a taste of the region’s great outdoors driving alongside Cape Cod National Seashore, and then stroll through the shops in Provincetown.

Before settling in at your vacation home, make like a local and pick up a local delicacy: oysters and clams in Wellfleet. Shuck and enjoy them fresh from the sea with a crisp bottle of wine in your kitchen at day’s end.

The Hamptons

When tony New Yorkers want to escape the crowded city, they make for the Montauk Highway, driving to vacation homes dotting towns like Southampton, East Hampton and on to land’s end in Montauk.

montauk lighthouse
Head to the Montauk Lighthouse. (Photo: Getty Images)

The Hamptons has rightfully earned its reputation as the playground for the East Coast’s wealthy set; however, it’s completely possible to enjoy this stretch of quaint towns at any price point. Art lovers should plan a stop at the Parrish Art Museum in Water Mill, which is also home to the Insta-ready Corwith Windmill.

Stretch your legs on a hike at the Sagg Swamp Nature Preserve, and then pick up a bottle of chardonnay to drink at your vacation home from Wölffer Estate Vineyard in Sagaponack.

History lovers can read the tombstones at the historic South End Cemetery in East Hampton, and you’ll find views of the sea and coast at Hither Woods Preserve in Montauk — where it’s all but mandatory to pay a visit to the Montauk Point Lighthouse. Be sure to stop for the much-raved-about lobster roll at Lunch, a local favorite.

Charleston and Savannah

Can’t decide between visiting those two Southern belles, Charleston and Savannah? It’s easy to rest your head at home in one while road tripping to the other.

Charleston, South Carolina cobblestone street
Be charmed by Charleston. (Photo: Getty Images)

In Charleston, take a walking tour of the historic district, and to the Battery, past the pastel-colored homes of Rainbow Row, before stopping for photos at the iconic Pineapple Fountain along the waterfront. Savor dinner at one of the town’s many acclaimed restaurants, like Husk or FIG, and cap off your evening with live jazz at the Charleston Grill.

Drive two hours south to Savannah, and along the way, stop in Saint Helena to discover the region’s Gullah culture and history. Once in Savannah, you’ll want to wander the atmospheric, grassy squares marked by looming oak trees draped with tendrils of Spanish moss.

Take an architecture tour or traverse the town’s waterways on a boat tour. After dark, get your fright on during a ghost tour, and then unwind over dinner at The Olde Pink House.

Great Smoky Mountains

Gatlinburg, Tennessee, sits practically at the entrance to Great Smoky Mountains National Park, making it the perfect place to book your vacation home in the Smoky Mountains.

great smoky mountains at sunrise
Rise and shine in the Great Smoky Mountains. (Photo: Getty Images)

Start your road trip in Herbert Holt Park, home to a trout farm and children-only fishing area, fuel up with a chili dog from Parton’s Deli, and then check out any visitors center inside the park to get a map and park information.

If tubing’s your thing, head to the park’s Greenbrier area; if not, pack a picnic and venture over to Chimney Tops, where you can splash in the creek. The highest point in the Smokies, at 6,643 feet tall, Clingmans Dome has an observation tower with a soaring aerial view of the mountainous surrounds.

Back in downtown Gatlinburg, even pint-sized travelers who aren’t of age will dig Ole Smoky Distillery’s impressive compound, which is more of an entertainment complex than a mere moonshine tasting room. Indulge in samples and dance along to live music that takes place daily (pro tip: Try the moonshine-soaked cherries).

Florida’s Emerald Coast

Florida’s Emerald Coast is lined by one of the state’s most scenic two-lane roadways, 30A, which stretches between Panama City and Destin and through one of Florida’s sweetest towns: Seaside. There’s a reason the movie “The Truman Show” was set here — it’s about as idyllic a spot as you’ll find, well, anywhere.

waves crashing on the beach
Discover why it’s called the Emerald Coast. (Photo: Getty Images)

Fuel up for your drive with doughnuts and coffee (OK, fine — and some ice cream, too!) at Blue Mountain Beach Creamery before making your way to quirky Grayton Beach, whose motto is “Nice Dogs, Strange People.” Go kayaking or paddleboarding at Grayton Beach State Park before making your way to the shops and restaurants in WaterColor.

Next you’ll arrive in Seaside, arguably the jewel in 30A’s crown, where you’ll want to unpack and wander through the town center and pop by its food truck park filled with Airstream trailers hawking tasty fare.

The Turquoise Trail from Albuquerque to Santa Fe

The Turquoise Trail National Scenic Byway (Hwy 14) links Albuquerque to Santa Fe, winding through 15,000 square miles of central New Mexico.

You’ll pass through the quaint mining towns of Golden, Madrid and Cerrillos, all of which provide opportunities for leg-stretching and shopping for Native American art, jewelry and souvenirs.

red rocks and river in arizona
Drive beyond Santa Fe. (Photo: Getty Images)

Once in Santa Fe, you’ll quickly see why it’s best known for its thriving arts scene. More than 100 galleries line both sides of vibrant Canyon Road, some of which have larger-than-life outdoor installations and moving parts.

Next, stop by the Georgia O’Keeffe Museum, which is home to a rotating exhibition of more than 3,000 renowned artists’ original works. The museum is just a few blocks from Santa Fe Plaza, a historic central courtyard and the heart of the town. There’s street food, vendors selling handmade jewelry and great people-watching.

Colorado’s San Juan Skyway

When you pick a stay in Telluride, Colorado, you can travel the Old West in more comfort than people did back in the day thanks to the San Juan Skyway, a 236-mile loop winding through southwest Colorado.

main street in Telluride, Colorado
Take a stroll in Telluride. (Photo: Getty Images)

Stop off in historic towns and former mining camps (yes, Telluride had fairly modest roots), and marvel over the cliff dwellings in Mesa Verde National Park. When you reach the Million Dollar Highway, a 25-mile section of the San Juan, breathe deep and take it slow.

It’s up, up, up, to two miles above sea level on this at times scaryish stretch of the San Juan Skyway. Things drop off (quite literally) on the side of the road.

Oregon’s Cascade Lakes National Scenic Byway

Despite its rainy reputation, Bend is coveted by Portlanders as one of the West Coast’s best-kept secrets due to its glorious summers and craggy terrain.

mountain reflecting in lake with pink sky
Find your respite in Oregon. (Photo: Getty Images)

The Old Mill District, a historic area comprised of shops, restaurants and galleries, is intersected by a calm strip of the 252-mile Deschutes River, where families paddleboard and tube under pedestrian bridges.

Take a drive along the 66-mile Cascade Lakes National Scenic Byway, which slices through Deschutes National Forest and offers jaw-dropping mountain views of Mount Bachelor before passing by a sparkling string of alpine lakes where you’ll want to hop in a kayak or take a spin on a paddleboard.

Gold Coast, California

You can’t go wrong booking a home along California’s Gold Coast, where you’ll find one of the most popular coastal routes in the nation, the Pacific Coast Highway (PCH), stretching from San Francisco to Los Angeles.

About an hour outside San Francisco is Half Moon Bay, a stunning, moody cliffside beach town where you’ll want to stretch your legs and feel the salt air in your face before snapping a few Instagram-worthy shots. Further down the coast is Santa Cruz, home to redwood forests, beautiful beaches and a very 1960s vibe.

Past Santa Cruz, you’ll cross the Bixby Bridge, one of the tallest single-span concrete bridges in the world, and arrive at Big Sur, perhaps the most beloved spot along the PCH.

Further south, you’ll see where the Spanish Franciscans in the 18th century established Santa Barbara’s mission, which has acres of gardens and a surprisingly beautiful cemetery. Finally, the beachside community and celebrity playground of Malibu boasts some of Southern California’s most beautiful beaches, including Zuma Beach and Point Dume.