Lying between the North and South Forks of Long Island, Shelter Island is sometimes called the un-Hamptons; it is similar to those well-heeled communities on Long Island but without the glitz and glamour. Around 8,000 acres (four-and- a-half miles long and almost as wide) much of the island is protected wetlands. You come here for the lovely beaches, the laidback lifestyle - more bicycles than cars - and the seafood. The best places to stay on Shelter Island let you enjoy all three.
You could just hang out on one of the pristine beaches, but to get more out of the island, hire a bike and explore the many cycling trails. The southern part of the island is made of the 2,000-acre Mashomack Nature Preserve where you can spot ospreys, herons and egrets. You can also kayak through the tidal creeks, wetlands and salt marshes where you might spot terrapins, too.
Take the ferry over to North Fork where you will find acres of farmland and wineries. Indeed, you will be spoiled for choice as around 30 vineyards are easily reached, many of which are open for tours and wine-tasting.
The best places to stay in Shelter Island are popular during the summer months, so don’t leave it too late to book your stay.
Seaside hotel on Shelter Island with spectacular views. A tastefully renovated 1960s motel, the hotel, both intimate and lively, has a popular outdoor restaurant and bar. Each room has a private sundeck, hardwood floors and modern furnishings, and the hotel opens out onto a stunning private beach.