A series of villages strung along the eastern tip of Long Island, the Hamptons are a beloved summer escape for chic New Yorkers. With a combination of glammed up farmland and miles of gorgeous beaches, this summer colony continues to evolve each year with hot spot restaurants, stylish shops and charming boutique inns.
Perfect forFamilies | Foodies | Romantics | Style Mavens
When to goJune-August | September-November
Ideal length of stay3-5 Nights
Designing Your Journey
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
Experience the best of the Hamptons with a customized itinerary that includes special access, touring and exclusive reservations. Here is just one example of what our travel specialists can arrange for you.
Day 1: Southampton
Southampton is often considered the first village in the Hamptons and with its elegant, tree-lined streets, chic boutiques and excellent dining, it is the perfect introduction to the summer enclave. Spend the day perusing stylish beach wear and home design on Main Street and Jobs Lane, and then relax in the afternoon at Cooper’s Beach, a pristine stretch of sand and surf a few minute’s drive from town. Afterwards, dine at one of Indagare’s favorite restaurants in the village.
Day 2: Sag Harbor and Shelter Island
Sag Harbor, a former whaling village, lies on the inside of the fork, facing the Great Peconic Bay. The town is lined with quaint Victorian homes as well as excellent shopping and dining. Before sunset, take the nearby car ferry to Shelter Island, a quiet haven of waterfront estates and a few restaurants and dine at Sunset Beach, a buzzy alfresco spot that brings a little St. Barth’s flair to the crescent-shaped beach.
Day 3: East Hampton, Amagansett and Montauk
The largest and glitziest of the villages, East Hampton is naturally beautiful with a peaceful pond leading into the charming downtown and sprawling estates lining Lily Pond Lane. There are great boutiques in town and in nearby Amagansett, but don’t miss time at the Main Beach. Surfers can head east to Montauk for big breaks and surf scene. Afterwards, enjoy dinner at one of Montauk’s buzzy restaurants or return to East Hampton.
Where To Stay
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities, including upgrades, early check-in, breakfast, spa credits and more. Look for the Indagare Plus logo in the reviews.
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Topping Rose House
The first full-service hotel in the Hamptons, Topping Rose House has a relaxed yet sophisticated feel thanks to its beautiful property, central location and fantastic restaurant.
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The Inn at Windmill Lane
A relative newcomer it may be, but this haven of a hotel, situated within walking distance of Amagansett’s charming boutiques and cafés, fits right in on the East End: its grounds are manicured and its suites impeccably put-together, but the...
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