Reachable only by ferries, private boats, or small seaplanes, getting to Shelter Island is something of an adventure. And once you’re there, its turn-of-the-century charm, historical buildings, relaxed attitude, and endless nature preserves (that make up one-third of the island) captivate city escapees and year-round residents alike. This bucolic island has quaint restaurants that feel more like home kitchens, farmer’s markets at the island’s historical society, and silky stretches of beach on all sides. There’s hiking for every level at the shady Mashomack Preserve and summer afternoons are well-spent watching the harbor’s picturesque sailboats and kayaking on protected waters. Sprawl out on Hay Beach, with nests of piping clovers and views of Gardiner’s Bay and the unique Bug Light Lighthouse. Night-time brings a more elegant dining scene, though you’ll still feel the island’s carefree and casual spirit. For a bit more glamour, head to the Sunset Beach hotel, the island’s biggest party that ebbs and flows with arrivals from docking boats (and yachts).
Image disclaimer: Images represent the overall interior and furnishings of a property at the time photographs are taken. Owners do and will continue to decorate and change furnishings, beds, etc at their discretion and these updates/changes may not be reflected. Views of the property's closest beach areas may also be represented however these images may not reflect the view from the actual accommodation. Please check with our villa specialist at the time of making your reservation.
