Set between the North and South Forks of glamorous Long Island, Shelter Island is a wonderfully laid-back destination for an outdoorsy holiday with friends and family or as a couple. Accommodation options are wide-ranging, with everything from contemporary B&Bs to boutique seaside hotels fit for an array of tastes and budgets. Reputedly less glitzy than the nearby Hamptons, the best places to stay in Shelter Island are brilliant for an active, outdoorsy escape.
Just 32 km2 in size, the island is fringed by fantastic beaches, which are ideal for long walks, sandcastle-building or sunbathing. There’s ample opportunity to go swimming, paddle boarding, sailing and wind surfing, too. Head inland to discover meandering cycling trails and hiking paths, as well as the impressive Mashomack Nature Preserve, which covers almost a quarter of the island. These protected wetlands are home to ospreys, herons and egrets — perfect for bird watchers or wildlife enthusiasts. Explore on your own or take a guided tour to learn about the area’s rich biodiversity. The tidal creeks and salt marshes can also be navigated by kayak!
For tours and tastings of fabulous Long Island wineries, take the ferry across to North Fork. The delights of East Hampton and Montauk, on the other hand, are within easy reach by ferry to the south.
Unwind with delicious fresh seafood dinners and lazy evenings gazing up at the stars. On an island with more bicycles than cars, the secret is about embracing the slow life — and the best places to stay in Shelter Island will help you to do just that.