Luxury Travel Guide:
The Hamptons
The Hamptons
The Hamptons have long held a unique place in the American imagination—a coastal arc of towns and villages perched on the eastern tip of Long Island where farmland meets ocean, and luxury meets simplicity. What began in the 19th century as a series of fishing and farming communities slowly transformed into a haven for city dwellers, artists, and eventually, some of the country's most affluent families.
The arrival of the Long Island Rail Road in the 1870s connected the region to New York City and opened the door for vacationers seeking ocean air and pastoral calm. In the 20th century, its beaches, colonial architecture, and generous light drew painters like Jackson Pollock and writers like John Steinbeck. What followed was a delicate layering of culture, exclusivity, and tradition that shaped the Hamptons' identity.
Today, the region still retains a sense of escape. Though some pockets are undoubtedly luxurious and scene-driven, others remain quiet, almost rural. The charm of the Hamptons lies in its contrasts—you can spend one morning browsing a minimalist farmstand and the evening dining beneath twinkling lights at a harborfront restaurant. It is these juxtapositions that continue to draw travelers who seek more than just a beach vacation.
The Hamlets
The Hamptons are not a single destination but a tapestry of distinct communities, each with its own sense of place. From historic whaling villages to quiet farming outposts turned design havens, every corner of the East End offers a different rhythm. Some are refined and traditional, others artistic and walkable, and a few feel untouched, where nature leads the experience.
Southampton
As one of the oldest English settlements in the state (founded in 1640), Southampton is where the Hamptons began. It is also arguably the most polished of the villages, with historic homes lining tree-canopied streets, and a bustling Main Street filled with high-end boutiques and art galleries. The town has long been associated with New York society families, many of whom have summered here for generations.
The village centers around a small, walkable street lined with outdoor cafés and bistros, perfect for alfresco dining in the summer months. Shopping blends big-name brands like Zimmermann with thoughtfully curated boutiques such as AERIN and Tenet. A stroll through town or a quiet afternoon at Cooper’s Beach offers a glimpse into the town’s easygoing, established character.
Where to Eat
Cheese Shoppe – Go-to sandwich pickup destination. Be sure to get your order in with plenty of time!
Sant Ambroeus – Chic Italian café fare.
Tate’s Bake Shop – Beloved bakery.
Tutto Il Giorno – Elevated Italian fare in sleek, coastal-chic surroundings.
Le Charlot – Parisian bistro charm—ideal for oysters, steak frites, and a crisp Sancerre.
Dopo Argento - bistro-like Italian-Mediterranean dining in the heart of Southampton
Sag Harbor
Sag Harbor is one of the most distinct villages on the East End—a historic whaling port with deep roots and an enduring sense of place. Unlike its neighboring hamlets, it has a year-round community and a preserved architectural charm that feels more New England than Hamptons. The village has long attracted writers, artists, and those drawn to a slower pace and creative spirit.
The main street is compact, charming, and remarkably well-preserved. You won’t find many big-name brands here—Sag Harbor has been intentional in protecting its mix of independent boutiques, bookstores, home shops, and specialty stores. The village feels personal and lived-in. The street spills gently toward the water, ending in a harborfront park that's ideal for a slow stroll or a picnic with sandwiches from the local deli.
Where to Eat
Carissa’s – Artisanal baked goods
Sagtown Coffee – Espresso and charm
Le Bilboquet – Always buzzing and dressed to impress, this harbor-front French favorite is best known for high-energy vibe.
Tutto Il Giorno – Elevated Italian fare in sleek, coastal-chic surroundings.
Sag Harbor Tavern – A hidden-in-plain-sight gem with nautical charm and a crowd of laid-back regulars.
Sag Pizza – Thin-crust pies, communal tables, and a welcoming spot for families—kids love it.
Big Olaf – Grab a sweet treat at this institution.
East Hampton
East Hampton offers perhaps the best synthesis of the Hamptons' past and present. It is home to some of the most sought-after real estate on the East Coast, but also maintains lush green spaces, public beaches, and a walkable town center. The village green, Guild Hall, and iconic windmills nod to its colonial roots, while its designer stores and legendary dining institutions cement its status among elite destinations.
Historically, East Hampton attracted painters, poets, and patrons of the arts. The Pollock-Krasner House in nearby Springs pays tribute to this legacy. Today, the energy remains refined but understated—a place where classic New England meets coastal glamour.
Where to Eat
Carissa’s – Elevated baked goods and coffee.
Sant Ambroeus – Chic Italian café fare.
Round Swamp Farm – A Hamptons institution for prepared foods, pies, and produce. Great pastries & coffee.
John Papas Café – A Greek-American institution serving hearty breakfasts with no frills.
East Hampton Grill – A Hillstone classic with comfort-food favorites like the famous Ding’s crispy chicken sandwich and skillet cornbread.
Nick & Toni’s – A forever favorite for its wood oven, celebrity sightings, and California-Italian menu—worth the reservation.
Camp Rubirosa: A seasonal East Hampton pop-up from NYC's Rubirosa serving crisp thin-crust pies and Italian favorites in a camp-themed setting.
Swifty's at The Hedges Inn: A storied New York institution reimagined in East Hampton, offering classic American fare with polished charm located at the Hedges Inn.
Moby’s – Seasonal pop-up turned institution, known for wood-fired pizzas, chilled martinis, and the quintessential East End party vibe.
Sí Sí – a Greek-Mediterranean restaurant offering vibrant, seasonal cuisine with stunning harbor views and an expansive patio perfect for sunset dining.
Amagansett
Tucked between East Hampton and Montauk, Amagansett has quietly become one of the most desirable spots on the East End. It's more discreet than its neighbors but no less stylish. The town centers around a small cluster of boutiques, farmstands, and cafés, and feels more like a neighborhood than a destination.
Originally a farming and fishing village, Amagansett retains its understated charm with low-profile homes and quiet beaches. It's the kind of place where locals bike to the farmstand and spend mornings at the beach before heading to a relaxed dinner at a low-lit restaurant. The pace is slower, and the style is effortless.
Where to Eat
Amber Waves Market – Farmstand market with produce, house-made sourdough, fresh flowers, and specialty finds plus a café counter.
Il Buco al Mare – Wood-fired dishes, fresh crudo, and coastal wines in a breezy, design-forward setting.
Fini Pizza: A Brooklyn transplant serving elevated New York-style slices and Sicilian pies.
Doubles: A Caribbean-inspired eatery offering roti, doubles, smash burgers, and smoothies in a casual, picnic-style atmosphere.
Coche Comedor: Authentic Mexican cuisine with a focus on wood-fired dishes and an extensive tequila and mezcal selection.
Stephen Talkhouse: An iconic venue hosting live music from renowned and local artists, embodying the Hamptons' nightlife charm.
Montauk
Known as "The End," Montauk is the easternmost point of Long Island and carries a personality all its own—more untamed and unpolished than its western neighbors. Once a working fishing village, it still holds onto that gritty edge, but over the last several years has evolved into both an energetic social hub and a sought-after dining destination. The town now draws surfers, creatives, and travelers looking for a mix of barefoot luxury and laid-back authenticity.
Montauk’s appeal lies in its sense of space and freedom. With wide beaches, open bluffs, and panoramic water views, it’s become home to some of the East End’s most iconic restaurants—ranging from upscale waterfront spots to casual beachside hangouts. The scene flows naturally from daytime swims to sunset cocktails and live music, often ending around a fire pit with sand still on your feet.
Where to Eat
Bird on the Roof – A Montauk staple offering hearty breakfasts and a relaxed vibe, perfect for brunch enthusiasts.
Joni’s – Known for its organic and fresh ingredients, Joni's serves incredible breakfast and lunch.
Montauk Bake Shoppe – Famous for its jelly croissants and a variety of baked goods, this spot is a must-visit for pastry lovers.
Duryea’s – An iconic spot for lobster rolls and seafood platters, featuring waterfront dining with stunning sunset vistas.
Crow’s Nest – A romantic lakeside setting with fresh, organic fare and nightly fire pits.
Maverick’s Montauk – A sleek, upscale restaurant offering seafood and pasta dishes with floor-to-ceiling windows overlooking Fort Pond.
Navy Beach – Beachfront dining offering a relaxed vibe, perfect for enjoying seafood and cocktails with your toes in the sand.
Montauket – A local classic since the 1920s, it's the perfect place to sip local beer, enjoy live music, and watch the sunset over the bay.
Surf Lodge – Live music, cocktails, and a view.
Things to Do
The beauty of the Hamptons lies in its range—you can fill your days with beach walks, hiking trails, vineyard visits, and gallery stops, or you can do nothing at all. Whether you're chasing waves, exploring gardens, or simply lounging by the pool with a book, the pace is yours to set. Sometimes the greatest luxury is just the quiet escape from the city.
Beaches – From wide ocean stretches to calm bay inlets, the Hamptons offer some of the Northeast’s most beautiful beaches. Parking permits are typically required, so check local town websites in advance.
Parrish Art Museum – A cultural anchor of the East End, the Parrish showcases rotating exhibitions of American art inside a Herzog & de Meuron-designed building that blends seamlessly into the landscape.
LongHouse Reserve – Part sculpture garden, part botanical oasis, this immersive outdoor museum invites leisurely exploration among art, design, and nature.
East End Wineries – Spend an afternoon wine tasting at Wölffer Estate, known for its rosé and golden hour lawn concerts, or opt for a more casual setting at the Wölffer Wine Stand, ideal for families and picnics. For a traditional tasting, Duck Walk Vineyards offers classic varietals and expansive grounds.
Charter a Boat – Explore the coastline by sea with a private charter—whether for a champagne cruise, clamming excursion, or full-day adventure to Shelter Island.
Golf – The Hamptons are home to some of the country’s most exclusive courses, but public options are available.
Tennis – From private courts at hotels and estates to local clubs, tennis is a favorite East End pastime. Many towns offer short-term passes for visitors.
Wellness & Movement – From beachside yoga to infrared saunas and upscale fitness studios like Tracy Anderson, wellness is a major part of the local rhythm.
Where to Stay?
Choosing where to stay in the Hamptons often comes down to the kind of experience you're after. Each town has its own distinct aesthetic, from classic and polished to quiet and low-key, and your accommodations can help anchor your itinerary. Whether you're planning to spend your days by the beach, hopping between vineyards, or dining out each night, it’s worth identifying the rhythm you’re seeking and selecting a location that aligns with it.
The good news is you can’t really go wrong. But keep in mind that staying in Southampton and booking dinner in Montauk means navigating over an hour and a half of summer traffic in each direction. For a more seamless experience, consider where you'll be spending most of your time and choose a hotel that keeps you close to it.
The Maidstone
Just off the village green, The Maidstone is a vibrant boutique hotel with playful, Scandinavian-inspired interiors, an art-filled lounge, and a charming garden patio perfect for morning coffee or evening cocktails. It is ideal for travelers seeking style, walkability, and a splash of whimsy.
The Reform Club
Located in Amagansett, a quieter hamlet within the town of East Hampton, The Reform Club is all about privacy and understated luxury. With lush gardens, spacious suites, and a serene atmosphere, it is perfect for those looking to unplug in elevated surroundings.
The Roundtree
Tucked along Main Street but hidden behind leafy hedges, The Roundtree is a refined yet relaxed. With modern farm-style cottages, fire pits, and complimentary beach cruisers, it feels like staying at someone’s impeccably designed summer home.
Baron’s Cove
This waterfront gem delivers classic Americana with a maritime twist, including rocking chairs on the porch, harbor views, and cozy rooms with coastal flair. With a lively restaurant, saltwater pool, and walkable access to town, Baron’s Cove is perfect for couples or families who want a bit of everything.
Topping Rose House
This standout property is a luxury retreat with a culinary soul. Featuring a Jean-Georges restaurant, chic modern suites, and an outdoor pool surrounded by manicured gardens, it is ideal for travelers seeking full-service amenities and serious gastronomic appeal.
Gurney’s Montauk Resort & Seawater Spa
Gurney’s is the only luxury hotel in the Hamptons with direct private beach access. With a newly renovated spa, oceanfront dining, and packed summer programming, it is perfect for travelers seeking a full-service resort vibe with unbeatable ocean views.
Logistics
When to Visit
The best time to head East depends on what you want to do:
Peak Season (June – Labor Day) - This is peak Hamptons. Expect packed restaurants, fully booked hotels, and beach parking lots that fill early. The energy is high, social calendars are full, and every village is buzzing. Perfect for those who love the scene—long lunches, late dinners, and people-watching with a glass of rosé.
Shoulder Seasons (May & September) - Often considered the best time to visit. The weather is mild, restaurants and shops are still open, but the crowds have thinned. Farmstands are abundant in both spring and fall, and you can enjoy outdoor dining and nature walks without the summer frenzy.
Off Season (October – April) - The pace slows dramatically and many seasonal spots close, but the charm remains. Quiet villages, uncrowded trails, and cozy restaurants make for a peaceful getaway. It’s a time to explore the region’s year-round culture—local art, historic inns, and winter walks by the water.
How to Get Around
The Hamptons span a wide stretch of the East End, and while each hamlet is charmingly walkable, distances between them are not. Driving is by far the most convenient and reliable way to get around, especially in summer when ride-share availability is limited and unreliable.
Rent a car: Ideal for flexibility, especially if you plan to explore multiple towns or head to Montauk.
Car services: Local companies like Hampton Car Service, East End Taxi, and Surf Taxi Montauk are more dependable than Uber or Lyft. Booking in advance is highly recommended, particularly for evenings and weekends.
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