Shelter Island Summer 2018


The perfect weekend getaway, Shelter Island is accessible by boat, car, train, or (private) plane!  And a short ferry ride, of course…

Often called the “un-Hamptons,” this scenic and peaceful island offers the same pristine beaches and great dining and nightlife without any of the congestion and pretension.

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Where to eat:

Ram’s Head Inn

This iconic Shelter Island hotel and restaurant is located high on a hill overlooking Coecles Harbor.  Catch live jazz or a local band in their cocktail and music lounge, “Harbor Hall”, and order off their local sourced and seafood heavy menu.  Grab a room to extend your stay.  Accessible by car, boat, or seaplane.


An island hot spot and celeb hangout, Isola offers fresh and simple Italian fare and a great bar scene and cocktail list.  Live music most nights and porch seating perfect for people watching in the bustling Historic Heights District make this a go-to on summer nights.

Caci Shelter Island

Caci Shelter Island is located just up the hill from scenic Crescent Beach, in the historic Shelter Island House hotel.  Offering a seasonally inspired menu featuring authentic Northern and Central Italian specialties, the cuisine is inventive and dedicated to all things house-made and authentic. Guests can choose to be seated in any of the three intimate dining rooms, cozy bar area, spacious covered patio, or opt to enjoy the Happy Hour menu at the bar, outdoor lounge, or on the bocce court.

What to do:

Piccozzi’s Bike Rental

Rent a bike to explore the island.  No better way to see the sites!

Venture Out Paddleboards

Rent paddleboards during the day on Crescent Beach and paddle out for a closer view of the yachts moored for the day, or give them a call and they will deliver boards to you anywhere on the island for maximum exploring.  The best way to see the island is from the water!

Shelter Island Pilates & Barre

Drop into any barre or yoga class or book a private Pilates session with former ballerina and choreographer Suzette Smith.  Her rigorous and uplifting classes are the perfect way to kick off your day to feel toned and refreshed before heading off to the beach!


Shelter Island Country Club/Goat Hill is a public course offering 9 holes of golf, a driving range and a bar and restaurant to relax in since 1901.


Being that you are on an island, there is sure to be a beach that fits your sun bathing style.  Hit Crescent Beach for a singles scene, Wades Beach for family fun, Shell Beach for easy boat access, or Hay Beach for privacy, just to name a few.

What to see:

Shelter Island Fireworks

Now in its 61st year, this island tradition is always held the Saturday after the 4th of July, and is an all day, can’t miss event held on Crescent Beach. If you can, snag a dinner reservation at Sunset Beach or the Pridwin Hotel for front row seats with waiter service, if not bring a picnic and settle in on the beach. July 7th, 2018, 9pm. Rain date July 8th.

Perlman Music Program

The Perlman Music Program is a summer program for gifted young musicians. Founded by Toby Perlman, wife of Israeli-American violinist Itzhak Perlman, in 1995, the program is headquartered in Shelter Island, and offers live concerts by students and guest performers at their beachfront location all summer long.

Mashomack Preserve

Comprising 1/3 of Shelter Island, Mashomack Nature Preserve is 2100 acres of natural habitat, edged in white by 10 miles of coastline, and an area of magnificent scenic beauty. Its combination of interlacing tidal creeks, woodlands, fields and coastline makes it a superb wildlife habitat, and perfect for a day of hiking and exploring


Grab a bottle of wine and head to Crescent Beach to watch the sunset.  Or head to the bar at Sunset Beach (located on Crescent Beach), order one of their famous mohitos, and relax.

For a full list of island businesses and attractions, please visit the website for the Shelter Island Chamber of

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