A Complete Guide to Spending Summer in The Hamptons

May 24, 2023
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In the Hamptons, where wild roses and lush green grass blend with sandy dunes and iconic grey-shingled homes, summer is just sunnier. Life in the Hamptons is more languid and relaxed than anywhere else, and this legendary area is famous for stunning estates and high-profile denizens looking for a respite from New York City heat.

From the equestrian elegance of Bridgehampton real estate to the grandeur of sprawling Sag Harbor homes, the prestige of the Hamptons community is widely known. This summer, trade the concrete and blaring horns of Manhattan for the cool breezes and tranquil village vibes of the Hamptons. This complete guide to the enclave’s bespoke summer activities will have you wishing for an endless summer.

Eat, drink, and be merry

From exclusive restaurants to celebrated vineyards, epicurean excellence reaches new heights in the Hamptons. The warm sun and clear blue skies set the scene for long, lazy luncheons, while that fresh ocean air stimulates the appetite like nothing else. These are the top ways you can eat and drink your way through a delicious summer season.

Mavericks Montauk

51 S Edgemere St, Montauk, NY 11954

The interior design of Mavericks Montauk is sleek, modern, and impossibly elegant. The streamlined furnishings and simple color scheme create an ideal canvas on which the celebrated chefs can splash a gourmet rainbow of exquisite dishes. Stop in for an apres beach snack of caviar and cold water oysters, or dine the night away with the sumptuous chilled seafood tower and lobster radiatori.

Le Bilboquet

1 Long Wharf, Sag Harbor, NY

Fruits de mer take center stage at this stylish harborside hotspot. Perched on the shore of Sag Harbor, Le Bilboquet showcases French cuisine at its most refined. The waterfront terrace is a beautiful spot for lunch, and the menu of fresh seafood is impeccable. Even the most refined palate will appreciate the yellowfin tuna with sea urchin vinaigrette, the tuna tartare, and the indulgent caviar calvisius imperial.

Lobster rolls

Buttery, decadent, and the ultimate in seaside indulgence – lobster rolls are a specialty of the Hamptons and, as such, deserve their own category. This quintessential beach town snack is simple but, when done right, captures the bliss of a perfect summer day, all in one delectable sandwich. From Duryea’s Montauk in Montauk to the Lobster Roll in Amagansett, make the rounds of the hottest lobster roll shacks and judge for yourself.

Wine tasting

Wineries line the lush landscape of the Hamptons, inviting sun-soaked revelers to relax with a crisp glass of award-winning pinot grigio or rosé. From Bridgehampton’s quaint Channing Daughters Winery to the stylish digs at Sagaponack’s Wolffer Estate Vineyard, wine tasting is a must-try addition to your summer activity list.

A day at the beach

Fill your cutest tote with sunscreen, flip flops, and the latest thriller – it’s time to indulge in what the Hamptons does best. The sand is soft, the beaches are rugged, and the landscape is breathtaking. From the long swath of shoreline at Two Mile Hollow Beach in East Hampton to the surf and swim hotspot Ditch Plains Beach in Montauk, beach-going in the Hamptons is a way of life. Each area of the Hamptons boasts a particular amenity and setting, so get ready to explore and feel the sand between your toes.

Set sail

Nautical style in the Hamptons means more than just anchor decor and navy and red striped swimsuits. Many properties in the Hamptons sport private docks and boat slips, allowing residents to set sail any time they please. Sailboats are available for rent all over the enclave, and water sports like wakeboarding and waterskiing rank high on the seaside dance card of activities.

Visit the Old Hook Windmill

The word iconic gets thrown around a lot regarding the Hamptons, but this storied spot certainly deserves the title. A beloved historic landmark, the Old Hook Windmill was built in 1806 and remained in operation for over a century. Today this whimsical spot gets attention every summer as residents swing by for a stroll and a photo. The elegant grey and white structure represents the classic Hamptons aesthetic and serves as an Insta-worthy spot for selfies.

Focus on health and wellness

Summer is for relaxing, and no one does it quite like the well-heeled denizens of the Hamptons. From fitness guru Tracy Anderson and her new studio in Sag Harbor to Gwyneth Paltrow’s famed Goop store, residents and visitors have every opportunity to glow up and chill out. Spas line the pretty, quaint streets, and the demure storefronts belie the bevy of world-class services and superb hospitality available to clientele.

Go for a ride

Horses are a major part of summer in the Hamptons, and there are countless ways to enjoy the equestrian scene. While Bridgehampton is known for gorgeous equestrian estates, you can find beautifully appointed stables in every corner of the Hamptons. From show barns and top trainers to equine rescue barns and beginner lessons, this tony area is a bastion of first-class horse farms and stables.

If you prefer to leave show jumping and dressage to the professionals, you can still enjoy the prestige and elegance of riding with the Hampton Classic, one of the area’s most exclusive events. This lavish horse show is a coveted social event and serves as the final party of the summer season. The Hamptons Classic has been on the social calendar for over 40 years and is the place to see and be seen, whether you show up in britches and riding boots or a designer dress and Hermes flats. The perfect way to celebrate the close of the summer season, the Hampton Classic is one of the summer’s most fashionable parties.

Christopher Covert of the esteemed Modlin Group is a highly sought-after luxury specialist focusing on the kind of ultraluxe estates for which the Hamptons are known. With a background in data analysis and real estate investing, Chris is poised to advise every type of buyer, from a family looking for a Hamptons vacation home to major investors looking for the next killer deal. Chris’s clients praise his professionalism, unparalleled knowledge of every corner of the Hamptons market, and his easy and efficient approach.

If you are ready to take your Hamptons search to the next level, contact Chris today to begin touring properties and see what Bridgehampton, Water Mill, and Sag Harbor, NY, real estate have to offer.

*Header photo courtesy of Unsplash

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