Whether looking for a romantic getaway near NYC or an adventurous escape from the ordinary, our Shelter Island boutique hotel offers luxury, romance and the perfect location near the beach. View some of our favorite things to do on Shelter Island and join us for an incredible getaway on Long Island.

Things to do in Shelter Island, NY - Beaches


Surrounded by beaches there is no shortage of sand, sea shells and swimming. Our closest beach is just a block walk to Cresent Beach where you can stroll the half mile strip or rent paddle boards from Venture Out. For the kids, Wades Beach hosts the family scene and head to the cut for the best fiddlehead catching in town! If quiet and piping plovers are your thing try the peninsula at Shell Beach.

Shelter Island Fishing


Flush with outdoor activities you have opportunities for everyone! If being on the water is your thing, let Shelter Island Kayak Tours take you on the water trail or grab a snapper pole from Jack’s Marine and hit the town docks for the catch of the day! Don’t want to miss your workouts, find group fitness classes and a full gym at Shelter Island Yoga and Fitness. Take the kids to the Whale’s Tale for mini golf or the Tuck Shop for ice cream and games.  Interested in organic farming check out the Sylvester Manor Educational Farm and grab some fresh eats from the farm stand to bring home.

Shelter Island Farmers Market

Area Attractions

With 2000 arces dedicated to the Nature preserve, you won’t want to miss a walk in Mashamock where wildlife and scenic views abound featuring trails for all fitness levels. Explore the history of Shelter Island at the Historic Haven’s House which hosts numerous weekend fairs and local Shelter Island Farmer’s Market. For an adventure take a private tour of Taylor’s Island. A fan of music, enjoy a fresh air concert at the Perlman School of Music, where musically gifted students of the strings give free performances to the public.

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The Tavern bar


Of course you won’t want to miss Shelter Island House’s own on premise Osprey Bar & Lounge, but a great alternate is our sister restaurant Salt Waterfront Bar and Grill at The Island Boatyard for local flavor and a laid back atmosphere. Only a 5 minute stroll and you can dine at Sunset Beach Restaurant for dinner & a nightlife scene or enjoy a family setting at the Shelter Island Country Club. Thinking American Bistro, try Vine St. Cafe or the Red Maple at the Chequit Hotel.