Visit the Hamptons and Shelter Island

When you visit the South Fork of Long Island, you step into a world of luxury. Feel like a celebrity while walking down the streets of the Hamptons, or enjoy a coastal getaway unlike any other on Shelter Island. Enjoy three days of coastal elegance and island charm by setting off on this itinerary made just for you.

Day 1

Start your Hamptons visit with a trip to Downtown Sag Harbor. This historic whaling village is now home to several boutique shops, waterfront views, and cafes full of life that stand out against the rest of the Hamptons. Take a stroll down Main Street and see what's waiting for you.

As sunset falls over the horizon, you'll want to head to Cupsogue Beach to see it. Westhampton's miles of soft sand and Atlantic Ocean make this the ideal sunset spot of the Hamptons. When night comes, check into Barons Cove, an upscale waterfront retreat with cozy-chic rooms that are just steps away from Main Street.

Cupsogue Beach County Park

906 Dune Road
(631) 852-8111

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. This…

Barons Cove

31 West Water Street
(631) 725-2101

THE HOTEL The Hotel features 67 charming village & harbor facing rooms and suites. Our family friendly amenities include the harbor side heated saltwater pool, tennis court, fitness studio, spa services, complimentary beach service with transportation. And be sure to speak to our concierge who can…

Day 2

Enjoy a day of art and wine along the South Fork! Immerse yourself in the local art scene when you visit Guild Hall of East Hampton. Inside, you'll find visual art exhibits, theater. live performances, and more.

Head to Sagaponack next to have a taste of the Long Island wine scene. Wolffer Estate Vineyard, one of the few vineyards in the Hamptons, offers world-renowned rose and artisanal bites along the vines.

Guild Hall of East Hampton

158 Main Street
(631) 324-0806

Guild Hall is the cultural heart of the East End: a museum, performing arts, and education center, founded in 1931. We invite everyone to experience the endless possibilities of the arts: to open minds to what art can be; inspire creativity and conversation; and have fun. Guild Hall presents more…

Wolffer Estate Vineyard

139 Sagg Road
(631) 537-5106

Surrounded by 55 acres of vines Wolffer Estate delivers the exceptional from wine tastings and tours to formal social events. Open daily from 11:00am -6:00pm or visit our web site.

Day 3

With your Hamptons checklist complete, take the ferry out of Sag Harbor to Shelter Island where you'll enjoy scenic views of Peconic Bay along the way. Looking for a quiet spot to unwind when you arrive? Head to the secluded Shell Beach. This calm stretch of sand is the perfect place to go kayaking, find some shells to take as a souvenir, or just unplug.

Check into the Ram's Head Inn for the night, a beautifully restored inn now included with modern amenities. You'll find rooms with wraparound porches and even onsite dining to top off your relaxed Shelter Island visit.

Shell Beach

Shell Beach

For a serene and tranquil beach visit on Shelter Island, Shell Beach is your destination. This narrow stretch of land extending into Shelter Island Sound is a stark contrast to the wider beaches on the Island. With its warm waters, vibrant wildflowers, and stunning views of West Neck Harbor and the…

Ram's Head Inn

108 Ram Island Drive
(631) 749-0811

A scenic, relaxing Shelter Island seaside resort with gracious country accommodations and a highly acclaimed world-class dining experience. A year round waterfront property.

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