Destinations Explored

1

The Hamptons

Map with locations highlighted

Leave behind the hustle and bustle of NYC in favor of an extended weekend exploring the best of the East End—from Montauk to Sag Harbor, Southampton to the North Fork. Whether you're in it for the beach, the wine, the food, the shopping, or the small-town charm, this itinerary will do the trick. 

Key Highlights

Spend time on your private yacht to get some sun from the ocean

Watch the sunset from the picturesque Montauk Point

Taste and explore the best wineries the Hamptons and North Fork have to offer

Soak up the sun from the best and most beautiful beaches in the Hamptons

Best Times to Visit

June - August

Sample Trip Itinerary

Day 1-5

The Hamptons

2.5 to 3 hour drive from NYC

Accommodation in The Hamptons

Suggested options (actual bookings will vary based on pricing and availability)

Relax at The Beach Club (Gurney's Montauk)

The Beach Club at Gurney's spans a 2,000-foot private beach. With beach chairs, umbrellas, and king-sized daybeds lining the sand, it's the perfect spot to sit back and relax for a bit. And if you get hungry, look no further than their summery menu of appetizers, sandwiches, salads, and cocktails. 

Head to Montauk State Point Park to see the lighthouse

Montauk State Point Park, which sits at the easternmost tip of Long Island, boasts some of the best views of the Atlantic Ocean as it converges with the Block Island Sound. It's here where you'll find the oldest lighthouse in New York State, which was commissioned by President George Washington in 1792. It recently underwent the first phase of an extensive renovation project to restore the historic sandstone and mortar. 

Want to spend more time here? Take a walk along the rocky shoreline or go surf fishing, which is especially popular when striped bass are in the area. 

Unwind on Sunset Beach

Right by the inlet where Lake Montauk feeds into the Block Island Sound (across from Montauk County Park) is Sunset Beach, a sandy stretch with ample space to perch yourself for the afternoon. Catch some rays, take a walk along the shore, and, if you get hungry, head around the bend to the area that lines Lake Montauk. Here you'll find casual outdoor restaurants (think clam bars and chowder houses). 

Enjoy a wine tasting at Channing Daughters

With a cool Atlantic breeze that creates a hospitable growing climate, Channing Daughters is able to harvest a unique selection of white and red grape varietals, including Chardonnay, Pinot Grigio, Tocai Friulano, Sauvignon Blanc, Merlot, Blaufränkisch, Syrah, Cabernet Franc, Refosco, and Lagrein. (They're the only winery on the East End producing wines from many of these grapes.) With 28 acres of vines, this intimate winery and tasting room is the perfect pit-stop on your second day in The Hamptons. 

Continue your wine tasting at Wölffer Estate Vineyard

Wölffer Estate Vineyard has been welcoming guests to its sustainable vineyard in the heart of The Hamptons since 1988. A lot may have changed since then, but its commitment to premium, distinctive wines, ciders, and spirits has not. With 470 acres (which includes the 55-acre sustainable farm vineyard in Sagaponack, 52 acres on the North Fork, 200 acres in Mendoza, Argentina, and 2.5 acres in Mallorca, Spain), Wölffer's reach is international—and always sustainable. In fact, for the sixth year in a row, they have been recognized by Long Island Sustainable Winegrowing. Don't miss their summer-inspired line, Rooted in Rosé, which includes the iconic Summer In A Bottle, as well as No. 139 Dry Ciders and non-alcoholic Verjus made from vinifera grapes. 

View local art at the Parrish Art Museum

Founded in 1898, the Parrish Art Museum celebrates the creative legacy of the East End, as well as its global impact on the art world. The collection spans more than 3,000 works, and they host 15 temporary annual exhibits. The building, which was designed by the acclaimed architectural firm Herzog & de Meuron and sits on14 acres of verdant meadow land, is worth admiring in and of itself. 

Wander and window shop through the town of Southampton

Located in the heart of Southampton Village is the bustling, charming Main Street lined with boutiques, art galleries, restaurants, ice cream shops, bookstores, and more. Pop into Citarella for a bite if you get hungry, and don't miss Sip 'N Soda for an old-fashioned scoop that'll satisfy your sweet tooth. 

Spend the day at Cooper's Beach (a Hampton favorite!)

Coopers Beach is an iconic Southampton spot that is often rated among the top 10 beaches in America. With full facilities (concession stand, bathrooms, outdoor showers, chairs/umbrella rentals), it's the ideal sandy stretch to spend the day relaxing, swimming, and strolling along the coastline. 

Spend your morning hiking the Quogue Wildlife Refuge

This 300-acre property of protected land features seven miles of trails that weave through forests, ponds, bogs, wetlands, and a tidal estuary—as well as the ecologically-rare Dwarf Pines in the Pine Barrens. There's even an Outdoor Wildlife Complex, which houses injured animals that require human care to survive, including owls, falcons, foxes, and a bald eagle. 

Enjoy a wine tasting at Macari Vineyards

Macari Vineyards is located up a steep, sandy slope along the North Fork, a 30-mile peninsula on the East End of Long Island that's recognized for its stellar wines. With a tasting flight accompanied by à la carte imported artisanal cheese and charcuterie, you'll receive a tasting of five featured wines and learn about the viticultural process from a Macari Wine Educator.

Sip farmhouse wines at Shinn Estate Vineyards

Shinn Estate is a winery, vineyard, and Farmhouse Inn located in a quaint, 125-year-old barn that has been passed down from generation to generation of Long Island farmers. 13 grape varietals are grown across 28 acres, with 72,000 bottles produced annually. What's more, the cellar, which is set apart from the winery in a barn constructed from reclaimed ancient heartwood pine, has solar panels on its roof that, along with wind turbine, produce all the energy for the winery, cellar, vineyard, and inn. The outdoor garden is the perfect spot to enjoy a tasting. 

Tour and taste wines at the family-owned Duck Walk Vineyards

Duckwalk Vineyards is one of the most recognizable—and respected—names in the East End. It spans 140 acres and produces upwards of 5,000 cases of wine annually, from Vidal Ice Wine made with grapes frozen on the vine, to Blueberry Port crafted with wild blueberries sourced from Maine. Choose between a wine tasting, wine by the glass, and wine by the bottle. And if you can make it there on Saturday or Sunday between 1:30 and 5:30pm, you'll be treated to live music! 

Set sail for your private yacht charter

Aboard this large, luxurious yacht, you'll find ample seating, a swim platform, paddle boards, swim floats, and a private changing area. There's also a hot and cold deck shower and refrigerator/freezer space—perfect if you bring your own food and drinks on board instead of opting for catering. One-way and round-trip excursions to Sunset Beach in Shelter Island are also available. 

Explore Sag Harbor Village

Sag Harbor is the epitome of small-town charm—and one of Long Island's hidden gems. When you stroll down Main Street, you'll pass hole-in-the-wall independent restaurants, boutiques, art galleries, and more. 

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The Hamptons

The Hamptons

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Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

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Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

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Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”

Testimonial Profile Image

Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

Testimonial Profile Image

Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

Testimonial Profile Image

Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”