Each summer, visitors flock to the Hamptons, a string of charming villages along Long Island's easternmost coast that are among the 10 best beach vacation destinations in the U.S. Blessed with beautiful stretches of sand along the Atlantic Ocean, as well as buzzy shopping and dining scenes, the Hamptons are rightfully famous as the ultimate summertime playground. However, travelers seeking a slower pace away from the Hamptons' crowds should venture north to Shelter Island, a 27-square-mile island
with abundant history, chic accommodations, and unspoiled nature that's only accessible by a short ferry ride or boat.
The island was originally inhabited by the Manhanset tribe of Native Americans, whose name for the island meant "island sheltered by islands" and from which it earned the name Shelter Island. It was later settled by British colonists in the 17th century, and by the mid-19th century, it was accessible by ferry service from the North and South Forks of Long Island. As the Hamptons have grown in popularity and visitors, Shelter Island has retained its tranquil and under-the-radar atmosphere. Today, the idyllic isle is an ideal day trip or weekend getaway, offering quiet beaches, hiking trails, boating adventures, delicious dining, historic sights, and boutique hotels.
Shelter Island's blissful charms are easy to access from the island's North or South Ferry service, which operate year round. The North Ferry departs from Greenport, a quaint historic town full of shopping and picturesque views, and the South Ferry departs from North Haven, near Sag Harbor, on the South Fork. The best time to visit Shelter Island is between May and October, as many businesses close on the island during the winter.
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What To See And Do On Shelter Island
Once you've made the short ferry crossing over to Shelter Island from charming Greenport or historic and serene Sag Harbor, the island's 8,000 acres beg to be explored. Beach lovers should head to Crescent Beach on the northwestern coast, not far from the Greenport ferry terminal. The half-mile sweep of golden sand washed by calm, clear waters is watched over by lifeguards, and the beach is perfect for basking on the sand or heading into the water to kayak or paddleboard. Near the ferry dock on the island's southern shore is family-friendly Wades Beach, also a wide, sandy swath on the tranquil Shelter Island Sound with lifeguards and a large parking lot.
To explore Shelter Island by the water, head out on an excursion with Tubby Charters. Captain John, who has lived on Shelter Island for nearly 60 years, leads half-day fishing charters in Peconic Bay to catch fish like fluke, blowfish, and black bass. For a more leisurely day on the water, Tubby Charters also offers three-hour sunset cruises for up to six guests. "Might be the best thing to do on Shelter Island," raved a Yelp reviewer. "Captain John knows the island like the back of his hand and every trip is a boat ride and a history lesson of the island all wrapped into one."
Active types can also head to Mashomack Preserve, a protected landscape of almost 2,400 acres. This picturesque terrain can be explored by trails of varying lengths that bypass rocky beaches, forests, ponds, and marshlands. Nearby, golfers can tee off at the public Shelter Island Country Club, which dates to 1901 and is on the National Register for Historic Places. To see more history on the island, venture to Shelter Island Heights, a small harbor-front community noted for its Victorian-era architecture.
Where To Stay And Eat On Shelter Island
Though Shelter Island is petite, its clutch of restaurants and hotels match the sophisticated charm of the nearby Hamptons. One of the island's most beloved establishments is Sunset Beach, overlooking the stunning Crescent Beach. Channeling the joie de vivre of St. Tropez beach clubs, the stylish hideaway is a popular spot for lively weekend brunches, cocktails as the sun sets over the bay, and romantic dinners on the lantern-lit, alfresco terrace. In-the-know travelers should book one of Sunset Beach's 20 guest rooms to enjoy lounging on Crescent Beach, shopping at the hotel's well-curated boutique, and savoring many meals at the buzzy restaurant.
Further down the road from Sunset Beach lies the Pridwin Hotel and Cottages, a historic hotel that dates to 1927 with coastal-chic interiors. There are 33 rooms in the main hotel and 16 standalone cottages that are perfect for families needing space or couples seeking privacy. Amenities abound, such as a large outdoor swimming pool overlooking the water, tennis courts, water sports rentals, and much more. Even if you're not staying in house, stop by the hotel for dinner at the elegant Terrace restaurant or a drink at the convivial Crescent Bar.
On the island's quiet and secluded northeastern peninsula, The Ram's Head Inn, one of the most romantic hotels in the northeast U.S., is a grand shingled inn built in 1919 with just 13 rooms and suites. Unlike many other hotels on Shelter Island, Ram's Head Inn is open year-round. Here, guests can swim and sunbathe at the inn's beach on Ram's Head Cove in summer, and enjoy delicious fireside meals and wine tastings in the winter. However, at any time of year, don't miss the chance to enjoy brunch or dinner at the inn's signature restaurant.
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Read the original article on Islands.
