Sailing in the Hamptons: Discover Shelter Island

Hamptons Real Estate (Shelter Island). Image Source: Sotheby's International Realty.

At the tip of Long Island in New York, less than two hours away from Manhattan, lies the Hamptons, a collection of seaside towns known famously as a playground for the rich. Think obscenely huge summer “cottages”, “Ladies-who-lunch” , and benefit charity balls. In the midst of this extreme wealth lies Shelter Island, a hamlet known more for its natural beauty and sailing culture than its trendy shops.

Nestled between the peninsulas of East and West Hampton, Shelter Island boasts a nature preserve, a pristine harbor, and dozens of historic landmarks. The island is accessible only by boat. You can drive your car onto the ferry from Greenport to the West and Sag Harbor to the East.

Shelter Island’s picturesque harbor catches your eye immediately. On a clear day, blue sky and sunshine sparkling on the water highlight sailboats bobbing in their slips. Sailboats line the docks of the Shelter Island Yacht Club.

The Yacht Club was founded in 1886 by the growing population of summer residents who docked their boats in the harbor. Its original purpose was to provide social events and opportunities for racing and recreational sailing.

Over the years the Shelter Island Yacht club has expanded to meet the needs of a growing population of year-round residents and seasonal visitors. Today it boasts a full service bar and dining room which welcomes both members and non-members. Members participate in regularly organized races and sailing regattas.

The Yacht Club also provides instruction for youth. In the summer months, children whose families come to vacation at Shelter Island can learn the sport of sailing.

Club members can also access boat and maintenance services from Yacht Club staff. If there is a service or part needed that may be inaccessible on the Island, you can be sure to get the best referral. Recreational sailors and racers alike need to find just the right sailboat propeller for their craft.

If you are not completely consumed with sailing while on Shelter Island, check out the Mashomack Preserve, the Perlman Music Institute, and the Union Chapel. Each of these landmarks will further your knowledge of the area and enrich your appreciation for Shelter Island.

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