Whether you’re planning a weekend getaway or an extended summer escape, the Hamptons offers a quintessential mix of relaxed coastal charm, incredible food, and breathtaking views. From ocean breezes to world-class dining, here are 10 must-do activities to add to your Hamptons itinerary.
1. Sip Rose at Wölffer Estate Vineyard
No trip to the Hamptons is complete without a visit to Wölffer Estate Vineyard in Sagaponack. Famous for its iconic Summer in a Bottle Rosé, this lush estate feels straight out of the European countryside. Book a table on the terrace, order a charcuterie board, and sip wine while taking in rolling vineyard views.
2. Explore & Shop Around Sag Harbor
For a charming, historical village feel, spend an afternoon wandering through Sag Harbor. Its walkable Main Street is lined with boutique shops, antique stores, and local art galleries. It’s the perfect place to pick up unique home goods, resort wear, or a great book before heading to the water.
3. Take a Day Trip Out to Montauk
Drive all the way to “The End” of Long Island and spend a day in Montauk. Known for its surf culture and laid-back energy, Montauk brings a rugged contrast to the polished towns nearby. Explore the scenic cliffs, watch the surfers, and soak in the relaxed coastal vibe.
- Duryea’s Lobster Deck or The Clam Bar: Indulge in classic lobster rolls and fresh raw bar staples right by the water.
- Sunset at The Montauket: Grab a casual drink and join locals on the lawn for the best sunset view over Fort Pond Bay.
- The Surf Lodge: Grab a spot on the deck overlooking Fort Pond for late-afternoon rosé, live acoustic sets, and one of the most high-energy, stylish golden-hour scenes on the East End.
- Boutique Hopping in Montauk Village: Skip the souvenir shops and browse curated beachwear, home goods, and high-end coastal design at spots like Wyld Blue, Melet Mercantile, and Whalebone General Store.
- The Crow’s Nest: Nestled over Lake Montauk, this is arguably the dreamiest dinner spot in town. Arrive early for a cocktail on the sprawling lawn that slopes down to a private beach.
- Beach Fire at South Edison: Book a local concierge service to set up a private, styled bonfire complete with Adirondack chairs, blankets, and a gourmet s’mores kit right on the sand.
4. Rent Open-Air Jeeps
One of the absolute best ways to experience the East End is on four wheels with the top down. Renting a Jeep gives you ultimate freedom—drive down tree-lined lanes, feel the salt air, and cruise from village to village with effortless, effortless beach style.
5. Visit Local Farm Stands
The Hamptons is home to some of the finest agricultural spots in the region. Stop by local farm stands (like Amber Waves or Round Swamp Farm) to pick up fresh heirloom tomatoes, local berries, homemade pies, and fresh-cut flowers. It’s a true staple of East End living.
6. Indulge in Exceptional Local Dining
The dining scene in the Hamptons is world-class, but two places stand out for a dynamic dinner on a girls’ trip:
- Lulu Kitchen & Bar (Sag Harbor): Known for its wood-fired cooking, vibrant atmosphere, and excellent seafood and steaks.
- Moby’s (East Hampton): Set in a stylish coastal venue with a lush backyard lawn, serving delicious pizzas, pastas, and refreshing cocktails.
- Nick & Toni’s (East Hampton): A legendary fine-dining institution famous for wood-oven Italian dishes, seasonal local ingredients, and frequent celebrity sightings.
- Crow’s Nest (Montauk): A dreamy waterfront restaurant perched on Lake Montauk offering Mediterranean-inspired fare, bonfire seating, and stunning sunset views.
- Tutti Manti / The Golden Pear (Bridgehampton/Amagansett): Perfect for upscale casual bites, fresh salads, and local community charm.
7. Grab Coffee & Pastries at Carissa’s
Start your morning with a artisan caffeine fix and baked goods:
- Carissa’s Bakery (East Hampton & Sag Harbor): A local favorite known for its striking modern design, artisan sourdoughs, delicate pastries, and expertly crafted espresso.
- Sant Ambroeus (East Hampton & Southampton): Brings classic Milanese elegance to the Hamptons with decadent Italian espresso, rich cornetti, and exquisite pastries.
- Jack’s Stir Brew Coffee (Amagansett): The quintessential shade-tree spot for organic drip coffees, matcha lattes, and vegan bakery treats.
- Tate’s Bake Shop (Southampton): The birthplace of the world-famous thin, crispy cookies—visit the original shop for fresh-baked desserts and coffee.
8. Relax at Iconic Beaches
From calm bay shorelines to dramatic Atlantic surf breaks, the East End boasts some of the country’s best beaches:
- Foster Memorial Beach / Long Beach (Sag Harbor): A calm bay beach with warm, shallow waters, ideal for paddleboarding, kayaking, and family picnics.
- Ditch Plains Beach (Montauk): Famous for its dramatic cliffs, world-class surf breaks, and iconic food trucks.
- Coopers Beach (Southampton): Consistently ranked among the top beaches in America, featuring wide stretches of white sand, rolling dunes, and historic mansion backdrops.
- Main Beach (East Hampton): A pristine oceanfront beach perfect for long sunset walks and ocean swims.
9. Feast on Fresh Lobster for Lunch
Embrace classic coastal living by ordering a fresh lobster roll or a full lobster lunch. Whether you grab a casual roll from a roadside shack like Lunch (The Lobster Roll) in Amagansett or enjoy seafood fresh off the docks in Montauk, dining on fresh catch while overlooking the water is a non-negotiable experience.
10. Take in Breathtaking Coastal Views
Wrap up your trip by soaking in the area’s iconic vistas and waterfront panoramas:
- Shelter Island Ferry & Sunset Beach: Catch the quick ferry across the bay to Shelter Island for picturesque harbor views, quiet coastal roads, and golden hour dining.
- Montauk Point Lighthouse: Visit New York’s oldest lighthouse at the eastern tip for sweeping panoramas where the Block Island Sound meets the Atlantic Ocean.
- Le Bilboquet (Sag Harbor): Grab a seaside table for upscale French dining paired with front-row sunset views over the marina.
- Camp Hero State Park (Montauk): Offers dramatic, rugged bluffs rising high above the ocean with trails overlooking dense forests and crashing waves.
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