For those who measure distance not in miles but in moments, the great American road trip takes on a new identity in the hands of the luxury traveler. This isn’t about pit stops and playlists—it’s about curated experiences stitched together by winding coastal highways, vineyard-lined backroads, and scenic mountain passes. When done right, the open road becomes a runway for indulgence—where every detour is a discovery, every hotel key unlocks another lavish layer, and the in-between moments are as polished as the destinations themselves. These five road trips across the U.S. offer the ultimate summertime sophistication, converging five-star stays, unforgettable dining, and curated experiences worth the extra miles.
Pacific Coast Reverie: Malibu to Big Sur
This legendary drive down California’s Highway 1 is pure luxury on a cliff’s edge, where the scent of eucalyptus mixes with ocean spray and the scenery reads like a movie reel. Start your escape at the serene and exclusive Nobu Ryokan Malibu, where minimalist Japanese design and sweeping sea views set the tone. Head north to Santa Barbara, stopping for a vineyard tasting at Sunstone Winery before checking into Hotel Californian, where Moroccan tiling, coastal glamour, and rooftop lounges make lingering inevitable. In Big Sur, the journey reaches its crescendo at Post Ranch Inn, perched high above the Pacific with floor-to-ceiling views, private hot tubs, and an eco-luxe ethos that feels like Earth’s reward for making it this far. Dine at the Michelin-starred Caruso’s in Montecito for refined Italian by the sea, or indulge in the ever-changing tasting menu at Sierra Mar, suspended above the surf. For an unforgettable finish, book a private helicopter ride back to LA—or simply take the long way home again.
Countryside & Culture: Hudson Valley to The Berkshires
New York to Massachusetts
Trade city heat for rolling hills, heirloom estates, and a cultural circuit framed in green. Begin your escape into the countryside at Wildflower Farms, Auberge Resorts Collection, where wild meadows and mountain views create an elegant pastoral hideaway. In Hudson, spend the afternoon antique-hunting or schedule a private tasting at Millbrook Vineyards, then settle in at The Maker Hotel, an eclectic townhouse retreat for creatives and aesthetes. Continue into the Berkshires, checking into the turreted grandeur of Blantyre, where fireplaces crackle and the wine cellar seems bottomless. Dinner options range from candlelit charm at The Old Inn on the Green to artful plates at Blue Hill at Stone Barns en route. Art lovers can reserve a private tour at MASS MoCA, and music aficionados won’t want to miss an evening at Tanglewood, the summer home of the Boston Symphony Orchestra, best enjoyed with champagne and a shaded private box.
Rocky Mountain Majesty: Telluride to Aspen
Colorado
This route through the San Juan and Elk Mountains fuses cinematic drama with alpine decadence. Begin in Telluride at Dunton Hot Springs, a restored 19th-century mining town turned ultra-luxury retreat where log cabins feature soaking tubs and sommelier-led dinners unfold beneath the stars. Wind along the Million Dollar Highway, stopping for high-altitude views, waterfall hikes, and artisanal coffee in Ouray. In Aspen, check into the iconic Hotel Jerome, Auberge Resorts Collection, where historic elegance meets elevated modern comfort. For dining, savor bold, mountain-inspired cuisine at 221 South Oak in Telluride, then move on to the Michelin-starred Element 47 in Aspen for truffle-dusted indulgence and rare vintages. Add a private fly-fishing lesson, a heli-hiking adventure into untouched wilderness, or a sunrise hot air balloon ride over Snowmass for an unforgettable immersion in alpine splendor.
Southern Grace: Charleston to Savannah
South Carolina to Georgia
A drive through the Lowcountry is less about distance and more about savoring every slow, honey-lit mile. In Charleston, check into The Loutrel, a refined Art Deco-inspired stay with rooftop views of church steeples and sea breezes, or opt for the polished Southern charm of The Dewberry Charleston. Meander through cobblestone streets, then retreat to a long, lingering dinner at FIG, where James Beard–worthy dishes meet Lowcountry comfort. Follow the coastline south through salt marshes and canopies of moss-draped oaks. Charter a sunset yacht cruise through the estuaries or stop for oysters along the way. In Savannah, settle into Perry Lane Hotel, and book a table at The Grey, a mid-century bus terminal turned icon of contemporary Southern cuisine, and wrap the day with a bourbon tasting or private carriage ride beneath lantern-lit squares.
Desert Luxe: Scottsdale to Santa Fe
Arizona to New Mexico
To begin your road trip into the desert, journey into Scottsdale, where Sanctuary Camelback Mountain delivers tranquil casitas, infinity pools, and spa rituals infused with desert botanicals. Head north through Sedona, stopping at L’Auberge de Sedona, where red rock vistas meet creekside cottages and fine dining under the stars. Book a guided vortex tour or browse Tlaquepaque’s high-end galleries. Continue east through the painted landscapes of northern Arizona until you arrive in Santa Fe, where Bishop’s Lodge, Auberge Resorts Collection offers adobe elegance, curated experiences, and a palpable connection to place. Feast on wild game and chile-spiced creations at Geronimo, sip mezcal at La Reina, or plan a private art crawl through Canyon Road’s elite studios. Cap the evening with rooftop stargazing and a telescope session guided by a local astronomer—it’s the kind of cosmic luxury only the high desert can deliver.