Hiding in Plain Sight: Shelter Island

20150827_123333Mention Shelter Island and many New Yorkers will nod their heads and say they have heard of it, but haven’t really been, but boy are they missing out! About a two hour drive from the city to Greenport, Long Island followed by a short five minute ferry ride across the sound and Voila! — you’re in one of the most scenic location that seems to be lost in time, and you’ll wonder why didn’t you visit sooner.


Amongst the many treasures of this island, a stay at the Gatsby-era Pridwin Hotel is a must; it fits perfectly into the American old-school tradition of low-key family resorts.  It is very reminiscent of the movie “Dirty Dancing”, especially if you get there just in time for their super popular Wednesday evening Cookout. The scene is like the opening sequence of the movie – with families hanging out on the front lawn set up with tables covered in white, the setting sun, the smoking grill and kids running around.

The newly painted deck dining area is the perfect spot to hang out all day if you choose to do so, with fabulous views of the bay, passing sailboats, folks jetskiing and standup boarding. Of course keep an eye for Alfred, the resident Seagull named after the famous writer Alfred Hitchcock and his Birds movie reference — he’ll have an eye on your food.

Glenn Gissler Design has had a long association with the Pridwin, and have been making improvements in stages, keeping the historic nature of the property in mind.


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Rent bikes at the hotel and take a spin around the Island and you will find many other jewels like the pretty Dering Harbor area parked with Teak Sailboats, the protected Osprey Bird nests and the colonial era Sylvester Manor which is a must see.

Sylvester Manor, with its grand white front gates which are a landmark on the Island, is actually a series of buildings. It has been in the same family since it was built in 1652 and the current owner Bennett Konesni is reinventing it as an Educational Farm. Here are some interior shots that photographers Sue and Steve Gross, our longtime collaborators, took for their book “Farm House Revival”.

Other notable activities might be a bike ride over to Silver Beach; on the way you will pass Hampton style large gated properties with tall manicured hedges, private beaches and stunning views of Long Island Sound. The island has some sophisticated dining options: Sunset Beach and Salt — where the Spicey Jalapeno Margheritas are a must!




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