Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to the Hamptons.

By Valbona Twerdahl
Updated: September 05, 2018
Theo Morrison

With its vast white-sand beaches, charming, hydrangea-lined hamlets, and high-end boutiques and restaurants, the Hamptons are an ideal summer getaway with endless attractions for anyone looking for a beach vacation with a side of glitz. The east end of Long Island has become especially popular among celebrities and affluent New Yorkers who are drawn to its relaxed beach vibe and close proximity to the city—about a two-hour drive without traffic. From shopping in Southampton to dining out in Montauk, each Hamptons town is bursting with its own character. Want to explore the area like a local? Get in a car and follow this itinerary for the perfect vacation in the Hamptons:

Day One

If you’re arriving at lunchtime, your first stop should be The Seafood Shop on Montauk Highway in Wainscott. It’s a fish market, not a full service restaurant, but choose from that day’s catch and one of the fishmongers will fry up your choice and make you a sandwich while you wait. After eating, make your way to ℅ Maidstone, a green, pet-friendly boutique hotel on Route 27 in East Hampton. Check into one of 19 Scandinavian celebrity-inspired guestrooms, borrow a complimentary Kronan bike, and head back out again. Take a five-minute ride past pristine hedges and the gray-shingled town library and into the picturesque town of East Hampton Village for some shopping.

On Main Street, Roberta Freymann sells everything from dresses and bikinis to table linens and duvet covers, all in an irresistible rainbow of summery prints under the Roberta Roller Rabbit line. Slip on a colorful caftan and you’ll instantly look—and feel—like a local.

For fun home accessories, head around the corner to The Monogram Shop on Newtown Lane, where you can add your initials to anything from barware to bath towels. If you don’t have time to wait for monogramming but want to give your next dinner guests a chuckle, pick up a pack of cocktail napkins with cheeky inscriptions on them instead. A few doors away, Scoop Du Jour provides the perfect afternoon indulgence: warm, fresh-out-of-the-fryer Dreesen’s doughnuts sprinkled with cinnamon sugar or served plain.

If you’re looking to add some athleisure wear to your wardrobe, head no further than Tory Sport, Tory Burch’s sleek East Hampton outpost for fashionable golf, tennis, or swim-related clothing. Her lightweight performance leggings and chic rash guards are perfect for your late afternoon barre class or stand-up paddleboarding lesson with Elements Fitness, nearby.  

For an elegant dinner in an intimate and historic setting, look no further than 1770 House, an inn and restaurant on Main Street, where the menus change with the seasons and the service is impeccable. Insider’s tip: If you’re looking for a more relaxed experience, make your way to the inn’s downstairs restaurant, a cozy tavern serving hearty American classics. Or, if you prefer to dine al fresco, snag a waterside table at Bay Kitchen Bar on Three Mile Harbor. Order a steamed lobster and enjoy a beautiful sunset over the marina.

If you’re in the mood for a late night, head to Stephen Talkhouse, Amagansett’s intimate yet rowdy live music venue set in an old shingled house with white shutters. It’s notoriously unpretentious for the Hamptons even though its legendary stage has hosted everyone from local acts to Rock and Roll Hall of Famers like Billy Joel, Paul McCartney, and the Rolling Stones.

Day Two

Start your day with an early-morning outdoor yoga session with One Ocean Yoga at Channing Daughters Vineyard in Bridgehampton. Afterward, make your way to Estia’s Little Kitchen, an unassuming breakfast spot that draws locals with decadent breakfast burritos, Robbie’s Gringo Hash, and house-made hot sauces.

Next, swing by Round Swamp Farm’s Bridgehampton store to pick up garden-fresh salads and handpicked fruit for a light lunchtime picnic on the beach. Unlike the other beaches in the area, Sagg Main Beach in Sagaponack sells daily parking passes so you don’t have to worry about obtaining one in advance. A local favorite, Sagg Main is quiet and pristine—a long stretch of soft white sand flanked by undulating dunes and crashing waves.

One of the best places to enjoy happy hour in the Hamptons is at Wölffer Estate Vineyard, where wine-and-cheese pairings are served on a terrace overlooking rows upon rows of manicured vines and, if you time your visit correctly, a breathtaking sunset. Wölffer rosé is synonymous with summertime in the Hamptons and locals love it so much that they jokingly refer to it as “Wölffer water,” sipping it at lunch, dinner, and anytime in between. Don’t leave before buying a case to bring home—after tasting it, you’ll want to sip it all day too.  

If you’re craving Japanese for dinner, make your way over to Sushi Zuki in Watermill and order the tuna sandwich or the teriyaki chicken salad—both crowd pleasers. For a farm-to-table meal, Jean Georges at Topping Rose House in Bridgehampton serves locally sourced meat and fish, vegetables picked from gardens just outside the restaurant, and sea salt produced in Amagansett.  

After dinner, make your way to East Hampton’s Blue Parrot, a laid back Tex-Mex cantina that serves margaritas in mason jars and boasts celebrity investors such as Renée Zellweger and Ron Perelman. If you’re lucky, you might even get a surprise appearance—or performance—from investor Jon Bon Jovi or longtime patron and notorious beach bum Jimmy Buffet.

Day Three

Drive north to Sag Harbor for your last day out east. Start off with a quiet breakfast overlooking the harbor at Baron’s Cove hotel. You can’t go wrong ordering the brioche French toast with nutella, or the Baron Egg Wich with heirloom tomato and thick cut bacon.

Next, hit the shops. The best ones in town are devoted to eye-pleasing housewares, furniture, and knickknacks. Monc XIII, on Madison Street, offers a carefully curated assortment of new and vintage pieces from Europe, from leather-framed mirrors made in Denmark and 1960s Italian light fixtures, to stylish, British-made backgammon boards and marble serving bowls from Belgium. Up the block on Main Street, Sylvester & Co. sells enticing, minimalist gifts to dress up any home, including quirky floor mats, limited edition prints, Chardonnay-scented candles, and charcoal hand soap. Also on Main Street but closer to the harbor, Black Swan Antiques is a treasure trove of eclectic antiques and a true mom-and-pop shop, owned by a local married couple who love hunting for cool pieces with interesting stories. Next door, Harbor Books is a refuge for bookworms, complete with comfy leather chairs for reading.

For lunch, go to Cavaniola’s Gourmet on Division Street, a favorite of Food Network chef Ina Garten. Sample some imported cheeses from the hefty display, and order a roast turkey sandwich with asiago and roasted artichoke to go. Walk across Bay Street towards Peconic Bay and find a bench where you can sit, eat, and admire the bobbing boats docked at the Sag Harbor Yacht Club. On your way out of town stop for a caffeine fix at Jack’s Stir Brew on Division Street. (The Monty, a latte sweetened with maple syrup, is a great choice). Or, if you’d rather have an ice cream cone, head to Big Olaf on Wharf Street for a sweet end to a perfect three-day weekend.

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