Road trips invite a sense of freedom and openness for spontaneity that structured group tour vacations simply cannot emulate. You’re able to move at your own pace, stopping and going as you please—and those stops along the way often lead to chance encounters that ultimately become precious souvenir memories.
Ready to make some road trip memories of your own? Here is a curated collection of road trips across the USA that may inspire your next adventure.
HISTORIC ROUTE 66
Where: Chicago, IL, to Santa Monica, CA
Distance: 2,448 miles
Time Needed: 10 days to 2 weeks. If you’re pressed for time, you could also focus on shorter chunks of the famous drive, i.e. Albuquerque to Santa Monica or Chicago to Oklahoma City.
Route 66 is one of the world’s most popular bucket-list road trips—for good reason. Once upon a time the Mother Road served as the main artery of travel to the West, and that legacy lives on in the form of beloved relics sprinkled throughout the drive, such as Roy’s Motel & Cafe and Tower Conoco & U-Drop Inn Café. As Route 66 weaves through eight states and some 200 small towns, you’ll be exposed historic, folksy, quirky, and haunting slices of Americana, each one begging you to stop and explore. You’ll also experience diverse geography—plains, mesas, mountains, desert, and forest—plus natural treasures such as the Painted Desert and the Grand Canyon (an easy side-trip).
THE OVERSEAS HIGHWAY
Where: Florida – Miami to Key West
Distance: 166 miles
Time Needed: This 4-hour drive (without stops) deserves at least 4 days. Even better: Extend your road trip to a few weeks to truly sink into island time.
Turn up the Jimmy Buffet tunes while making the drive from Miami to Key West. The highway that connects mainland Florida to the far-flung Keys is an engineering marvel that stretches across open ocean into tropical paradise, no passport required. Start in Key Largo, where underwater reefs will lure you from the road to explore ocean waters by diving, snorkeling, and glass-bottom boating. End in Key West, where outlandish joie de vivre and tongue-in-cheek kitsch are colorful mainstays.
SAN JUAN SKYWAY LOOP
Where: Southwestern Colorado
Distance: 235 miles
Time Needed: You could drive the entire loop in 6 hours, but carve out several days to sink into the beauty and history that this mountainous landscape offers.
This road trip of thrilling twists and turns fuses together an Old West pioneer spirit with spectacular mountain beauty. The drive weaves through dense forest framed by 13,000-foot peaks, stringing together mountain towns each worth an overnight stay. Among them Durango, Telluride, Silverton and Ouray (a Victorian-era mining town nicknamed “The Switzerland of America”). The canyon-clinging part of the drive between Silverton and Ouray is part of The Million Dollar Highway, nicknamed either for its costly construction or the figurative price for its stunning San Juan Mountain views.
OREGON COAST HIGHWAY 101
Where: Portland, OR to Astoria, OR to Crescent City, CA
Distance: 363 miles
Time Needed: Budget at least 3 to 5 days, depending on how many stops you intend to make.
Highway 101, also known as the Pacific Coast Scenic Byway, features breathtaking views of rocky coastal formations and gorgeous beaches throughout the journey down Oregon’s coast. Aside from these postcard-perfect panoramas, attractions that beg for a stop include whale watching excursions in Depoe Bay and dune buggy tours on the Oregon Dunes in Florence. More than a dozen craft breweries dot the drive, helping to quench your thirst along the way. Tack on northern California to extend the road trip to see the Redwood forest and wine valleys north of San Francisco.
PACIFIC COAST HIGHWAY (PCH)
Where: California – San Francisco to Los Angeles
Total Distance: 500 miles
Time Needed: This trip can be savored in the span of 3 days or stretched out over 2 weeks, especially if you opt to travel further south to San Diego.
This is the classic California road trip. Beginning at the Golden Gate Bridge, you’ll wind down the PCH to a magnificent menagerie of beauty: gorgeous vistas, seaside villages, laid-back wineries, interesting wildlife, and world-class farm-to-table and ocean-to-table dining. The opportunities for stops range from the totally breathtaking, such as exploring Big Sur, home to a majestic stretch of rocky oceanfront cliffs, coastal redwood forests and panoramic beaches, to the totally bizarre, such as adding your wad of chewed-up bubblegum to Bubblegum Alley in San Luis Obispo, a cute gateway town to Central Coast Wine Country, which boasts more than 250 wineries.
THE BLUES HIGHWAY
Where: Nashville, TN to New Orleans, LA
Total Distance: 630 miles
Time Needed: Give yourself at least a week to truly savor the sights, sounds, and cuisine.
The roots of jazz, blues, soul, Cajun, zydeco, country, gospel, and rock ‘n’ roll are woven into this road trip. Start in Nashville, a.k.a. “Music City,” where more than 120 live music venues (including the legendary Grand Ole Opry) will inspire toe-tapping to some of the country’s best talent, before heading down to Memphis, a recording launching pad for legends such as Elvis and Johnny Cash, as well as home to Graceland and some of the country’s best BBQ. The route then follows the Mississippi River and Route 61 down to New Orleans, weaving through Mississippi towns such as Tunica and Clarksdale, which produced greats like Muddy Waters and John Lee Hooker and where you’ll find authentic bluesmen playing in real juke joints to this day. Along with an appetite for music, bring an appetite for food: southern culinary delights await, from fried catfish and crawfish to biscuits and beignets.
COASTAL MAINE
Where: Boston, MA to Bar Harbor, ME
Total Distance: 275 miles
Time Needed: Give yourself 3 to 7 days to savor this New England experience.
Lobsters, lighthouses, and loads of quaint seaside hamlets await you on this journey up the coast from Boston to Acadia National Park. New England towns like Kennebunkport, Portland, Camden, and Bar Harbor are just a few gems to visit along this route. Enjoy stunning fall foliage by timing the drive for autumn, when the forests that hug Maine’s coastline explode into brilliant hues of red, orange, and gold. If you can add the Schoodic National Scenic Parkway, a 95-mile roundtrip loop from Bar Harbor, you’ll be rewarded with uncrowded coastal views in a much quieter part of Acadia National Park.
THE LAS VEGAS LOOP
Where: Roundtrip from Las Vegas through Arizona, Utah, Nevada
Total Distance: 1,100 miles
Time Needed: This 19-hour loop deserves at least a week of vacation time.
Sin City is a launching pad to a road trip filled with national park adventures. Spend time exploring the otherworldly geological formations and red-hued canyon trails of national parks such as Zion National Park, Arches National Park, and Canyonlands National Park before returning to neon and glitz of Las Vegas for world-class cuisine, entertainment—and perhaps a spa day to soothe tired muscles and feet.
BLUE RIDGE PARKWAY
Where: Virginia & North Carolina – Waynesboro, VA, to Cherokee, NC (although many use the cities of Charlottesville and Asheville as start and end points, respectively)
Total Distance: 469 miles
Give yourself at least 3 to 5 days—more if you plan to spend substantial time exploring the national parks.
This road trip connects two national treasures, Shenandoah National Park and Great Smoky Mountains National Park. The winding blacktop follows the backbone of the Appalachian Mountains, a.k.a. the Blue Ridge, through the forests of western Virginia and North Carolina. On this slow meander (the speed limit is mostly 45 mph), you’ll encounter dramatic viewpoints of misty mountaintops, roaring waterfalls, and curious rock formations. Hiking opportunities abound, as does the chance to learn about Appalachian heritage at stops such as the Blue Ridge Music Center and Folk Art Center. With a melody of banjos, fiddles and guitars as your soundtrack, consider visiting this Smoky Mountain attraction founded by the region’s most beloved musical heroine: Dollywood.
