Activity

Cupsogue Beach

This 296 acre barrier beach park offers lifeguard supervised Atlantic Ocean swimming, sun bathing on white sand beaches, and some of the finest saltwater bass fishing on the Island. A snack bar, rest rooms, first aid center, shower, and changing rooms are all situated at Cupsogues pavilion.

Lunch

Cowfish, Hampton Bays

Located off-the-beaten-path in the Hampton Bays, Cowfish is a waterfront sanctuary on Shinnecock Bay complete with a grassy lawn filled with Adirondack chairs and a mini-playground perfect for restless children.  With classic New England style fare and a laid-back atmosphere this hidden gem is perfect.

Activity

Southampton History Museum

The Southampton History Museum was organized in 1898 and incorporated in 1910. By 1960 the Rogers Mansion property had expanded to include 12 historic structures including an 1830 one-room schoolhouse, an 1825 barn and a 19th century paint store, among others. Today, the museum has 4 separate properties with 14 historic buildings that contain changing exhibits

Dinner

Southampton Social Club

Pair land and sea with a selection of meats, sushi and fish. This fine dining spot offers lively nightlife and outdoor open space.

Accommodations

Southampton Inn

The Southampton Inn’s 90 luxury rooms are set on 5 manicured acres in Southampton village, within walking distance to village restaurants, boutiques, museums, galleries and nightlife.

Activity

Cooper’s Beach

Coopers Beach in Southampton is often rated among the Top Ten Beaches in America according to Dr. Beach, and is consistently named on the listing of America’s Top Ten Beaches. Visitors can enjoy the white sandy shores with the backdrop of nature and historic mansions.

Lunch

Almond

French bistro serving up seasonal dishes in a historic building with a hand carved bar. Almond often welcomes artists and writers for open mic nights.

Activity

Parrish Art Museum

The Parrish Art Museum celebrates the artistic legacy of Long Island’s East End, one of America’s most vital creative centers. Since the mid 1950s the Museum has grown from a small village art gallery into an important art museum with a collection of more than 2,600 works of art by contemporary painters and sculptors.

Activity

Wölffer Estate Vineyard

Wölffer is Long Island’s premier South Fork winery, operating since 1988. Insider Trip: try the Summer in a Bottle Rosé. The 55 acres of estate provide a pictureque background and private experience. The Private Pergola Experience includes a tour, pergola table reservation with small plates, wine tasting and special wine library bottle.

Dinner

East Hampton Grill

Classic American fare and comfort food paired with hand-picked wines and local produce.

Accommodations

The Maidstone

The Maidstone Hotel & Restaurant is open everyday, all year round for breakfast, brunch, lunch, cocktails, dinner, cocktails again and late night snacks. The hotel is right on East Hampton Main street, by the pond, just a short walk from the beach. The property has 16 rooms and 3 cottages, each dedicated and inspired by a Scandinavian luminary. Choose by design or personality and play the part.

Breakfast

The Baker House

A premiere Hamptons bed and breakfast. Nestled in the beautiful, historic Village of East Hampton, NY, The Baker House 1650 is a masterpiece of 17th Century Cotswold-inspired architecture while possessing the homey, yet majestic aura of a superb English manor.

Activity

Montauk Lighthouse Museum

This is the oldest lighthouse on Long Island, and also the oldest in New York State, completed in 1796 on a spot where the Royal Navy had maintained signal bonfires for its ships during the American Revolution. President George Washington authorized the construction of the lighthouse after many ships had been lost on the reefs at land’s end. Climb to the top of the lighthouse and tour the museum.

Activity

Surfing at Corey’s Wave

Whether it is your first time out or you are an experienced rider, CoreysWave can guide you down the path to becoming a better surfer. CoreysWave specializes in private and group surf lessons, stand-up paddling, personal surf training, kids’ surf classes, winter surfing and surfing in exotic locations.

Lunch

MTK Lobster House

MTK Lobster House’s original location is a staple in the local community of Montauk. Take part in their popular program “You Hook’Em, We Cook’Em.”

Activity

Montauk Brewing Company

Montauk Brewing Company, Long Island’s easternmost brewery, is housed in a red barn with the taproom, tiny outdoor patio and picnic tables reflecting the mellow Montauk mentality and, come summer, you’ll find people drinking blue cans of Montauk Summer Ale on the local beaches. The brewery produces some easily drinkable ales and, summer or not, the brewery churns out delicious seasonal one-offs, stouts, and Session IPAs.

Activity

Deep Hollow Ranch

Visit the oldest working ranch in the USA and go horseback riding on the beach.

Dinner

Tauk @ Trail’s End

The oldest restaurant in Montauk. This trendy eatery with LED lights and white-walled exterior is a reboot of a longtime American eatery which features an outdoor patio and live music.

Accommodations

Gurney’s Resort

Gurney’s has two properties in Montauk, Gurney’s Star Island Resort & Marina and Gurney’s Montauk Resort & Seawater Spa. At Gurney’s Star Island, there are 84 elegantly appointed guestrooms, all with outdoor terraces, and 23 select hideaway villa rooms offer a tranquil relaxing getaway. At Gurney’s Montauk Resort, there are 146 rooms, suites, and beachfront cottages, all delivering dramatic ocean views with direct acess to a 2,000-foot private sand beach.

Stay at the beach before you go home on the exclusive Gurney’s resort.