Easy U.S. Long Weekend Trips in the Fall

We’ve scoped out five perfect places for weekend getaways—or lengthier stays—all with hotels, restaurants and activities galore. These dynamic destinations guarantee something for all types of travelers, whether you’re looking for a retreat in the sun or the next foodie hotspot for wining and dining.

With the Santa Ynez mountains as a towering backdrop and the glimmering Pacific Ocean in the foreground, Montecito is a stylish enclave on Southern California’s coast, just east of Santa Barbara. Most hillside estates here—including those of Oprah Winfrey, Ellen Degeneres and the Duke and Duchess of Sussex—are private, but non-locals can (and should) visit Ganna Walksa Lotusland. The 20th-century Polish opera singer Ganna Walksa spent decades transforming this 37-acre property into her own personal Eden, with 25 different gardens. The town’s best shopping is on eucalyptus-shaded Coast Village Drive, with its Cali-quaint stores selling clothing, home furnishings and accessories. You can increase your haul at Rosewood Miramar Beach, home to five boutiques, including outposts of Brunello Cucinelli, Goop and a concept store curated by James Perse. The hotel’s appeal: on a long stretch of south-facing beachfront, Rosewood Miramar Beach’s public areas and 160 residential-style rooms, suites and bungalows embody a refined, slower pace of life, in which days involve lawn games, pool lounging and beach reads.

Epicureans and art lovers have plenty of reasons to visit this coastal Georgian city, where traditional historic antebellum architecture and warm Southern hospitality are complemented by renowned galleries and trendy restaurants. Reservations to make in advance: Husk and The Grey, from James Beard Award-winning chefs Sean Brock and Mashama Bailey, respectively, as well as Common Thread, from the family of beloved FARM in nearby Bluffton, South Carolina. These three restaurants each offer farm-to-fork Southern cuisine that simultaneously respects age-old traditions while looking forward. As for where to stay, the riverfront is buzzing with activity, most of it centered on the new (and huge) JW Marriott, which has transformed a former power plant into a vibrant shopping destination. For smaller-scale elegance, we love the chic boutique property Perry Lane Hotel, a few blocks in from the river. It celebrates the city’s roots and culture in its eclectic décor, including works by local artists, while bolstering Savannah’s culinary renaissance with its foodie focus: in addition to a restaurant and wine market, it has two cocktail bars, one inside and one on the spacious roof—the prime location for relaxing during weekend getaways.

Ski season in Aspen kicks off on November 27 this year, but the country’s most glamorous Alpine resort town is heaven for outdoor enthusiasts even when its slopes aren’t open. And in the fall, the town's namesake trees blanket the surrounding mountainsides in a golden yellow. Seemingly infinite miles of wilderness, 14,000-foot-high mountains and roaring rivers provide ample opportunities for hiking, biking, golf, paragliding, white-water rafting, horseback riding and rock climbing. Plus, adventurists who’ve reached their adrenaline quotient can return to the historic downtown, whose 19th-century brick buildings—which date to the town’s mining days—now house high-end boutiques and restaurants. Retail options include Rocky Mountain favorites, such as Pitkin County Dry Goods, a purveyor of accessories and leather coats since the 1960s, and bigger names like Ralph Lauren, Prada and Moncler. Aspen’s top restaurants to book: farm-to-table Meat & Cheese, chalet-chic French Alpine Bistro and comfort-food classic White House Tavern. Not surprisingly, the resort town is home to several fabulous hotels as well. Indagare members love The Little Nell for its intimate scale, cosseted atmosphere and attentive service and unparalleled location (adjacent to the Ajax Mountain gondola) and the St. Regis, which has a grander scale and the best spa in town.

With its avant-garde art and design districts, fusion culinary scene and seven-square-mile stretch of white-sand beach, Miami lures sun worshippers and culture hounds. And with the worst of hurricane season over, Southern Florida in the fall promises near-perfect weather for lounging poolside and dining alfresco. The “It” crowd can be seen at buzzy new restaurants, as well as more established spots such as South Beach’s Stubborn Seed, for tasting menus, and Zuma, for Izakaya-style Japanese cuisine in Brickell. Mid-Beach has some of the best resorts, including Faena—with its splashy and splurge-worthy Los Fuegos restaurant from Francis Mallmann—and The Edition. Both of these attract the stylish set, but are comfortably north of the rowdiness further down the beach. Even further removed is Four Seasons Hotel at the Surf Club, which feels worlds away but is barely 30 minutes by car.

If Miami in the late fall attracts the see-and-be-seen crowd, Maine, Martha’s Vineyard and Nantucket and the coast of Rhode Island draw travelers seeking peace and quiet. Temperatures hover in the 60s through November (Maine is more prone to the 50s), so there is plenty of opportunity for beach time—albeit lengthy strolls instead of hours in a cabana. This corner of New England is the ideal destination to combine action (biking, hiking, fishing and sailing are brisk and beautiful this time of year) with laid-back inaction. Make the most of good weather days outside, but save some time for browsing local boutiques in historic port towns and dining on classic New England cuisine like lobster rolls and clam chowder; Indagare members on a recent trip to the Kennebunkport area enjoyed meals at Mabel’s and Bandaloop. Our favorite hotels on New England’s coast, including Maine’s White Barn, Martha’s Vineyard’s Harbor View Hotel, Nantucket’s White Elephant Rhode Island’s Ocean House and Weekapaug Inn also warrant at least a few hours of lounging on-property, be it in a lawn chair or by the fireplace.