Golf clubs, fishing charters, and Montauk dive-bar nightcaps
The polo-shirt-and-rosé weekend — rent a Sagaponack house, lunch at Duryea's in Montauk, dinner at Nick & Toni's in East Hampton. Surf lesson with CoreysWave, an afternoon at Wolffer Estate Vineyard, late drinks at the Surf Lodge. Charter a Viking out of Montauk for the offshore run. Jitney up Friday, helicopter back if the group is feeling it.
beach • 2 hours
Group surf lesson at Ditch Plains Beach with instructors who specialize in making beginners look comfortable on a board within an hour.
cooking class • 3 hours
A Hamptons private chef leads the group through a seasonal coastal menu — fresh pasta, local clams, dessert — then everyone sits down and eats it together.
golf • 5 hr
RTJ-designed muni with ocean breeze on the back nine
fishing • Half day
Striped bass + tuna charters out of Montauk Harbor
lounge • balanced • $$$
Montauk's iconic waterfront lodge hosts live music on the dock every summer evening — the single best place to watch the sun drop into Fort Pond Bay.
Dress code: Linen and sundresses
cocktail bar • balanced • $$$
Bohemian Montauk motor lodge turned summer cocktail destination with a campfire pit, string lights, and an effortlessly cool crowd.
wine bar • chill • $$$
Italian-accented wine bar where the aperitivo hour runs long, the negronis are perfectly stirred, and every table looks like a Vogue editorial.
Dress code: Smart casual
bar • balanced • $$
Amagansett's legendary live-music roadhouse — artists from Norah Jones to The National have played here; the floor fills up and the night takes over.
cocktail bar • chill • $$$
Intimate East Hampton cocktail bar with a rotating seasonal menu and an impressive natural wine list that rewards leisurely sipping.
club • unhinged • $$$$
The Hamptons' closest thing to a proper nightclub — bottle service, a real dance floor, and a Saturday night energy that runs past midnight.
Dress code: Dressy
dive bar • balanced • $$
Legendary surf-town dive with live music most summer nights
Italian-Mediterranean • $$$$ • Best for: dinner
The Hamptons institution since 1988 — wood-fired Tuscan cooking and a regulars list that includes everyone who's anyone from June to Labor Day.
New American • $$$$ • Best for: group-dinner
Tom Colicchio's farm-to-table restaurant inside a Greek Revival mansion with produce from its own kitchen garden — elevated and deeply seasonal.
French Bistro • $$$ • Best for: brunch
Classic French bistro that locals swear by for weekend brunch — croque madame, a brilliant Bloody Mary, and a sun-drenched patio.
Bagels / Brunch • $ • Best for: brunch
The morning ritual for every Hamptons house share — proper New York bagels, exceptional lox, and a line that moves faster than it looks.
New American • $$$ • Best for: dinner
Nautical-modern dining room with a raw bar, excellent oysters, and a late-night energy that keeps the night alive well past dessert.
Italian Steakhouse • $$$$ • Best for: group-dinner
East Hampton steak + pasta institution — celebs, locals, and a real crew-dinner room
resort • Max 60 guests
Montauk's premier oceanfront resort with a seawater spa, private beach, and a social scene that starts at the pool and runs to the fire pits.
boutique-hotel • Max 44 guests
Meticulously restored Greek Revival estate with 22 rooms, a Tom Colicchio restaurant, and a pool garden that encourages long afternoons.
house • Max 16 guests
Cedar-shingled estates with pools, chef kitchens, and acres of privet hedge — the definitive group experience; book via Hamptons Real Estate or Airbnb Luxe.
boutique-hotel • Max 40 guests
South-of-France-meets-Montauk boutique hotel with a pool, fire pits, and an energy that reads more St. Tropez than Long Island.
The city that never sleeps won't let your party sleep either
The end of the world, the start of the party
Lake house, wakeboard charter, mountain views
Vineyard crawls, lake fishing, and bourbon barrel tastings with the crew
Cabin weekends, whiskey distilleries, and river fishing
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