Road Trip Planner: 5 Great U.S. Drives

The open road and the promise of a new discovery around the next bend: there is something extremely satisfying about the sense of freedom and adventure that comes with a driving trip. Whether you’re on a romantic weekend away with your partner or pointing out all the local sights with your kids in the back seat, summer and early autumn are the best times to hit the road. If you’re looking for inspiration for your next Great American Road Trip, Indagare has rounded up five of our favorite driving getaways in the U.S., from Maine to California.

Contact Indagare for assistance planning the perfect road trip for you. Our dedicated trip designers can match you with the best properties and restaurants along the way.

Note: Several attractions mentioned in this article, including most museums, are temporarily closed due to the ongoing Coronavirus pandemic. 

California Road Trip

The drive along the Big Sur coastline—a spectacular sweep of the Pacific Coast Highway—is one of America’s most beloved road trips for good reason. Start north in Napa Valley for a romantic food and wine retreat, or in San Francisco for a trendy urban immersion and a dose of culture at the de Young Museum or the Asian Art Museum. Start your trip by heading south from San Francisco and weaving through the fertile Santa Clara Valley, both a major tech hub and the artichoke capital of the world. The drive along the coast includes long stretches of empty road against the stunning backdrop of the Pacific and some of the best rest stops you could ask for, including the charming towns of Monterey and Carmel-by-the-Sea. For a night in Big Sur, romantics should stay at the Post Ranch Inn or Ventana, while families will appreciate the Carmel Valley Ranch. Further south, stop in the exclusive beach colony of Santa Barbara before finishing your trip in buzzing Los Angeles with a well-earned meal at one of the city’s top new restaurants.

Member Recommendations:
“In between Monterey and Santa Barbara lies an arid stretch of land specializing in Rhone varietals and undervalued wines (the two biggest being Granache and Syrah). A small cowboy town, Paso Robles is reminiscent of 1970s Napa: it’s wine country with breathtaking views and superior wines, but without any pretension.” – Indagare member Ashton Keefe. 

Related: Navigating the California Coast

American West Road Trip

Embark on an epic adventure through America’s former frontier. Start in Las Vegas and cross into the southwestern corner of Utah (for an additional excursion before leaving Nevada, the historic Hoover Dam is located less than an hour from Las Vegas). The neon intensity of the city gives way to the open, empty road as you continue to Zion National Park. Try to enter the park through the East Entrance, which is jaw-droppingly scenic. Spend some time hiking and exploring this majestic landscape. For more adventure, head to Bryce Canyon, known for its other-worldly landscapes and colorful limestone rocks. Drive to Amangiri, surrounded by 100 acres of sand-hued canyons near the border of Utah and Arizona, for a relaxing conclusion to your trip. The property houses a one-of-a kind pool built around the landscape, a 25,000-square-foot spa and several on-site hiking routes.

Member Recommendations:
“While hiking The Narrows in Zion, we happily tucked ourselves into the base of this tall slot canyon and navigated the chilly waters of the Virgin River (which at times was as high as mid-thigh) for three glorious hours.” – Indagare member AE Rueppel. Read more of AE’s recommendations from a family trip to Zion, the Grand Canyon and Sedona.

New England Road Trip

Begin in the seaside resort town of Newport with fresh seafood and a tour of the area’s historic mansions. From there, it’s a short drive to Boston, home to excellent dining and world-class museums, including the Museum of Fine Arts and the Isabella Stewart Gardner Museum—not to mention several historic day-trips (such as Concord and Walden Pond) as well as Fenway Park, a must-see for sports fans. From Boston, those looking for a taste of charming coastal New England should continue north to Maine, stopping in Bald Head for a stay at the sprawling oceanfront Cliff House and in the buzzing harbor town of Kennebunkport before wrapping up the road trip in Portland, where The Press Hotel offers a boutique experience in the heart of Old Port. Autumn road-trippers hoping for prime fall foliage viewing can veer west from Boston and head into Vermont instead. Less than three hours from Boston, the intimate and much-lauded Twin Farms is the ultimate rest stop. The all-inclusive property, set on 300 acres, epitomizes laidback luxury, and guests spend their days savoring the exquisite on-site cuisine, canoeing around Copper Pond and wandering the trails that wind from the guest cottages down through forests and fields. Since Twin Farms only accepts children during designated weeks, families can stay at the nearby Woodstock Inn & Resort, which offers hiking, kayaking, fishing, golf, tennis, horseback riding and tours of a working farm.

Member Recommendations:
“Long a favorite destination of ours, the Woodstock Inn is the quintessential New England experience. The premier location on the Woodstock Green is a plus for golfers, and the resort is just a short walk from town, which is teeming with charming shops and restaurants.” – Indagare member Lindsay Purcell. Read more of Lindsay’s recommendations in Vermont.

Related: On the Road With Kids Aged Six to Eleven

American South Road Trip

Immerse yourself in history on this journey through the South. Begin your road trip in one of the country’s earliest and most elegant cities: Charleston, South Carolina. Tour historic homes, enjoy a drink at The Belmont and spend the night in the cozy Zero George before setting off on your drive. About one-and-a-half hours from Charleston is beautiful Beaufort, the backdrop of several memorable movies, including The Big Chill and Forrest Gump. From there, it’s less than an hour to the Montage Palmetto Bluff, a waterfront hideaway with an award-winning golf course and bike paths draped in Spanish moss that promises a tranquil mid-trip stop before hitting the pavement once again. Savannah, Georgia is less than an hour away, where you can dine on innovative Southern fare in this burgeoning foodie capital and sip rooftop cocktails at the chic and whimsical Perry Lane Hotel. End your trip about two hours south of Savannah in the Golden Isles of Georgia with a stay at the oceanfront Sea Island resort for golfing, fishing and relaxing on the beach.

Member Recommendations:
“Our mini ‘Southern tour’ was like a living history lesson, made even more fun by seeing wonderful houses, gardens and landscapes. We also had some seriously good food along the way.” – Indagare member Pamela Murdock

American Southwest Road Trip

A Southwest road trip can combine the exciting cultural hubs of Texas and New Mexico with a stay at one of our favorite spa retreats in Arizona. Start in Dallas with a tour of the downtown arts district and a visit to the Renzo Piano-designed Nasher Sculpture Center, then drive about three hours to Austin for a shopping break in South Congress and a live music performance at the Continental Club or C-Boys Heart and Soul. Less than two hours from Austin is San Antonio, where visitors can stroll along the river walk or visit some of the city’s top museums, including the San Antonio Museum of Art, the McNay Art Museum and the Linda Pace Foundation. Art lovers should continue on to Marfa, a unique ghost town-meets-hipster enclave that is home to impressive art institutions such as the Chinati and Donald Judd Foundations, as well as the iconic Prada Marfa building and the mysterious Marfa lights. From there, it’s about seven hours across the border of New Mexico to reach Santa Fe, a colorful oasis in the desert that left a deep impression on American cultural influencers like Georgia O’Keeffe and Bob Dylan. Follow the path of the Anasazi through to the Cliff Palace of Mesa Verde and see the power of the sky and land at the Petrified Forest before ending your voyage in the red rock embrace of Mii amo and its rejuvenating spa, with an extensive treatment menu and daily roster of activities.

Member Recommendations:
“Go to Jeffrey’s for the most original high-end Austin food or go to Hudson’s out on Lake Way. The Four Seasons Austin is one of best I have ever stayed at anywhere, with an unbelievable brunch.” – Indagare member W.M. Read more Indagare members’ recommendations for a Texas road trip.

Related: Where to Stay & Eat During College Visits With Your Kids

Contact Indagare for assistance planning the perfect road trip for you. Our dedicated trip designers can match you with the best properties and restaurants along the way.

– Nikki Erlick on July 23, 2019

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