Our Insiders Guide To Summer In The Hamptons

Only a two hour drive from Manhattan (much less by helicopter or seaplane), the Hamptons are much more than just collection of cute hamlets and villages on the east end of Long Island. In fact, the Hamptons are well known to be thesummer playground for the rich, famous and best of all, interesting, because summer residents can be well-known writers, artists, top chefs, surfers, and farmers, in addition to Hollywood A-listers, and Wall Street moguls.

This tony enclave also offers the best of everything, from majestic beaches to haute home design, historic architecture, luxury fashion boutiques, boating, and a vibrant farm-to-table culinary scene. The Hamptons’ “high season” officially begins on Memorial Day weekend and ends on Labor Day. Here’s your fast track on how to do the Hamptons like an insider.

The Topping Rose House

Photograph provided By the Topping Rose House


Topping Rose House, Bridgehampton

This full-service Greek Revival luxury hotel was built in the 1840s and is home to 22 elegant guest rooms, as well as a Naturopathica spa, fitness center, pool, courtesy house vehicles from Lexus, and Jean-Georges’ farm-to-fork restaurant that showcases locally grown produce. toppingrosehouse.com

The Baker House 1650

Nestled in the historic East Hampton Village, The Baker House 1650 is a masterpiece of 17th-century Cotswold-inspired architecture. While possessing the majestic aura of a superb English manor, this tony bed-and-breakfast caters to guests with luxe modern accommodations and comforts, including a dreamy spa and private carriage house with suites you can rent all summer long. bakerhouse1650.com

Baron’s Cove, Sag Harbor

One of the area’s most buzzed about recent additions, Baron’s Cove boasts 67 beach chic rooms and suites—and it’s dog friendly, too. Amenities include a saltwater pool, tennis court, spa services, artisanal cocktails by the fire pit, and beach transport. baronscove.com

Baron’s Cove, Sag Harbor 

Photo by Trevor Tondro


Normandy House, First Neck, Southampton

If you’re looking to make a “Bobby Axelrod” summer splash, you rent a house, not a hotel room. Drive through the gates and alley of trees to your 8.4-acre magnificent estate, recently redesigned by Tony Ingrao. Grand entertaining spaces open to waterfront views and lush gardens. Don’t overpack though: Normandy House is only offered for two summer weeks…for $300,000. timdavishamptons.com

Southampton’s Normandy House

Photo by by Aerial Aesthetics


Aerin, Southampton

Aerin Lauder’s eponymous Southampton concept boutique offers fragrant candles, home accessories, coffee table books, perfectly folded tunics, and the ideal summer shade of Estée Lauder pink lipstick—Natch! aerin.com

World-class shopping in the Hamptons

Photo courtesy of Long Island CVB

Serena & Lily Beach Market, Wainscott

Style your own beach bungalow at this airy Hamptons outpost showcasing the California-based design duo’s favorite elements: color, pattern, comfort, and light. serenaandlily.com

Figue, East Hampton

A Bohemian lifestyle boutique founded by Stephanie von Watzdorf, Figue is known for its namesake clothing touting a resort spirit and global aesthetic. Readily embraced by the Hamptons gypset crowd. Figue’s core items include tunics, kaftans, shirtings, dresses, denim, and accessories in colorful, inspired prints. figue.com


Sant Ambroeus, Southampton

Old-school Hamptons blue bloods and the discreet Euro jet set have commingled here since 1992. A mani basse the best Italian cuisine on the East End. Dine alfresco for the best people watching. santambroeus.com/restaurant-sant-ambroeus-southampton/

The American Hotel, Sag Harbor

One of the most historic restaurants on the East End, this fine dining destination draws crowds with its American-French fusion cuisine and  award-winning wine list. If you can reserve the table “under the moose,” consider yourself a Hamptons VIP. theamericanhotel.com

The Surf Lodge, Montauk

Surfers, supermodels, fashion editors, and fishermen who look like models converge at this waterfront hipster hot spot on summer nights and all-day party weekends during its coveted Summer Concert series. Good luck at the door! thesurflodge.com


Murf’s Backstreet Tavern, Sag Harbor

Cool local dudes with beards and fun pretty girls shoot darts, play ring toss, and drink draft beers with the occasional city slicker who hears about this “secret” little spot. kdhamptons.com/business/murfs-backstreet-tavern/

The Montauket, Montauk

Game over! This is the best place to watch the sunset on the East End. The views are worth a million bucks, but don’t expect a signature drink menu, fancy design, or even a website for this very low-key locale for regulars.


Tate’s Bake Shop, Southampton

Kathleen King, queen of the $100 million chocolate chip cookie company, destroys the bikini-body dreams of all Hamptons girls with her irresistible sweet treats. tatesbakeshop.com

Left Hand Coffee, Montauk

A true espresso bar with a high design and laid-back vibe, this is where the surf set of Montauk turn to for a dose of caffeine and the ultimate hipster coffee klatch. lefthandcoffee.com

Round Swamp Farm, East Hampton

Just-out-of-the-oven homemade pies and muffins, freshly baked bread, fried chicken, dumplings, prepared foods, and more keep Hamptonites lined up out the door at this one-stop gourmet and family-owned farm stand. roundswampfarm.com


Aventura Motors, Southampton

Cruising in the Hamptons requires the coolest convertible. Ignite your passion for classic cars at Aventura Motors in Southampton. Take the wheel of your favorite German, British, Italian, or American vintage autos. aventuramotors.com


Barton & Gray Mariners Club offers members unlimited access to a fleet of crewed Hinckley yachts during the Hamptons high season. Sail at sunset from Sag Harbor to Shelter Island in style. bartonandgray.com


Take a 45-minute flight of fancy with Shoreline Aviation  in a handsome seaplane, high above the fray, from the East River in NYC to the East End. shorelineaviation.com


Wölffer Estate Vineyard, Sagaponack

Originally a potato farm, this vineyard is now a 175-acre storybook estate with a 55-acre vineyard, boarding stables, 30 paddocks, an indoor jumping Ring, and a Grand Prix field. Order your case of Summer in a Bottle rosé now—they sell out every summer. wolffer.com

Wölffer Estate Vineyard’s Summer In A Bottle rosé.

Channing Daughters Winery, Bridgehampton

Channing Daughters grows and creates wines from more than two dozen varieties across six vineyards. It specializes in white varietals and blends from Walter Channing’s first experiments, plus boasts an emerging interest in Italianate grape varieties. Don’t miss the Yoga in the Vines classes on weekends. channingdaughters.com

Cooper’s Beach, Southampton

Beloved by day-trippers and families alike, this glorious stretch of sand has been voted the country’s best beach many times. They also grill an epic cheeseburger at the ocean-front snack bar and host a drive-in movie night on Mondays. Try not to wince at the $45 parking fee; it’s worth it.

Surfing at Ditch Plains Beach

Ditch Plains Beach, Montauk

This beach is considered the Holy Grail of the Hamptons’ surf scene. Warning to city slickers who think they can surf: do not “drop in” on a local surfer’s wave here…you’ll be sorry.

Check out more of Kelli Delaney’s “Luxury Lifestyle Diary of the Hamptons” at kdhamptons.com.

Image Credits: photograph by shutterstock.