Nestled amidst the two distinct regions of Long Island, Shelter Island emerges as a remarkable summer sanctuary, offering a serene counterpoint to the bustling energy of the Hamptons. This charming isle, spanning 27 square miles, presents an alluring blend of historical depth, untouched natural beauty, and refined hospitality, all without the overwhelming crowds often associated with popular summer destinations. Its unique appeal lies in its secluded atmosphere, accessible primarily by a short ferry journey, making it an ideal choice for discerning travelers seeking tranquility and an authentic island experience away from the clamor.
For those looking to explore a lesser-known gem in the New York area, Shelter Island provides a captivating alternative. Historically significant, the island was originally known as \"island sheltered by islands\" by its native inhabitants, the Manhanset tribe, a name that perfectly encapsulates its sheltered allure. Later, in the 17th century, British colonists settled here, and by the mid-19th century, ferry services connected it to the North and South Forks of Long Island, solidifying its accessibility. Despite the increasing popularity of the nearby Hamptons, Shelter Island has steadfastly maintained its peaceful, understated charm, offering a refreshing escape.
Visitors to Shelter Island will find an abundance of activities to fill their days. The island is graced with quiet, pristine beaches, inviting hiking trails that wind through diverse landscapes, and numerous opportunities for boating adventures on its calm waters. Beyond its natural endowments, Shelter Island also boasts a vibrant culinary scene, serving up delectable dishes, and a collection of boutique hotels and historic sights that add to its allure. The optimal period to visit this idyllic spot stretches from May through October, as many local businesses tend to close during the quieter winter months, ensuring a lively and engaging experience during the warmer seasons.
Reaching Shelter Island is straightforward, with year-round ferry services departing from both the North and South Forks. The North Ferry embarks from Greenport, a quaint historic town known for its charming shops and scenic vistas, while the South Ferry sets sail from North Haven, situated near the elegant Sag Harbor. Upon arrival, the island's 8,000 acres await exploration. Beach enthusiasts will be drawn to Crescent Beach on the northwestern coast, a golden expanse of sand with tranquil waters, perfect for sunbathing, kayaking, or paddleboarding. On the southern shore, Wades Beach offers another family-friendly option with ample space and lifeguard supervision.
Beyond its shores, the island invites aquatic adventures. Tubby Charters, led by the seasoned Captain John, offers both exhilarating half-day fishing excursions in Peconic Bay and serene three-hour sunset cruises, providing not just breathtaking views but also insightful historical commentary on the island. For those who prefer land-based pursuits, the Mashomack Preserve, a protected area spanning nearly 2,400 acres, offers an intricate network of trails traversing diverse ecosystems, from rocky beaches to lush forests and marshlands. Golfers can enjoy a round at the historic Shelter Island Country Club, established in 1901 and listed on the National Register for Historic Places. A stroll through Shelter Island Heights reveals charming Victorian-era architecture, adding a touch of historical elegance to the visit.
Despite its modest size, Shelter Island boasts a sophisticated array of dining and lodging options that rival the Hamptons in elegance. Sunset Beach, perched overlooking Crescent Beach, embodies the vibrant spirit of St. Tropez beach clubs, making it a favored destination for lively weekend brunches, evening cocktails, and romantic alfresco dinners. Its twenty guest rooms offer an exclusive stay, complete with boutique shopping and exquisite dining. Further along, the historic Pridwin Hotel and Cottages, dating back to 1927, provides a blend of coastal chic and comprehensive amenities, including an outdoor pool, tennis courts, and watersports rentals, alongside fine dining at its Terrace restaurant and the convivial Crescent Bar.
On the island's tranquil northeastern peninsula, The Ram's Head Inn stands as a grand shingled structure from 1919, featuring just thirteen rooms and suites. This distinguished inn, unique for being open year-round, offers guests the opportunity to swim and sunbathe at its private beach on Ram's Head Cove during the summer. In colder months, the warmth of fireside meals and wine tastings creates a cozy retreat. Regardless of the season, a meal at the inn's signature restaurant for brunch or dinner is highly recommended, promising a delightful culinary experience that perfectly complements the island's peaceful charm.