Shelter Island Excursion

Shelter Island is a hidden gem located between the North and South Forks of Long Island. This tiny island is known for its 27 miles of natural beauty and homegrown community. Take a 2-day trip to this coastal escape and see some highlights of this region below.

Day 1

Arrive to Shelter Island's seaside charm in the morning. Once you're settled in, walk over to Crescent Beach, one of Shelter Island's most iconic shorelines. Take a swim in the warm waters, stroll along the sand, or just soak up some rays.

Top off your first day with a visit to The Chequit Tavern & Terrace for dinner. This elevated tavern menu offers seasonal favorites and the perfect cozy ambience for a night on the water. You can keep your stay on the water when you check into The Pridwin Hotel & Cottages, a historic waterfront resort with the perfect view of the bay.

Crescent Beach

Shore Road

Nestled on the northern side of Shelter Island, Crescent Beach, also known as Louis’ Beach, beckons visitors with its captivating views and wide sandy beaches. Overlooking Southold and Greenport, this beach provides a scenic backdrop for your beach day. It's the perfect spot for sunbathing, building…

The Chequit Tavern & Terrace

23 Grand Avenue
(631) 749-0018

Outdoor dining with harbor and sunset views. For a cozier, pubbier setting, meet us downstairs in the Tavern.

The Pridwin Hotel and Cottages

81 Shore Road
(844) 200-5001

The Pridwin Hotel and Cottages is a classic American resort hotel that has been providing guests a unique experience on Shelter Island since 1927. The nearly 10-acre site on Crescent Beach was selected for its protected waters, gentle bay breezes, and for its breathtaking water views of the Peconic…

Day 2

Start your second day with a morning hike through Mashomack Preserve. More than 2,000 acres of woodland call Shelter Island home, and you might even spot an osprey or deer along the way.

When your hike is through, enjoy dinner on the water at Sunset Beach Restaurant. You'll find the atmosphere of a European beach club inside paired with delicious cocktails and a brilliant view of the sunset.

Mashomack Preserve

79 S Ferry Rd
(631) 749-1001

Edged in white by 11 miles of coastline, Mashomack on Shelter Island is considered one of the richest habitats in the Northeast. Just 90 miles from New York City, the preserve covers over 2,350 acres of interlacing tidal creeks, mature oak woodlands, fields, freshwater marshes and underwater lands…