We’ve got a soft spot for Shelter Island, a historical little enclave that’s situated halfway between Long Island’s North Fork and the tony Hamptons. We chose this 8,000-acre getaway as the site of our first catalogue shoot for a few reasons. One is that there’s so much stunning coastal scenery. Another is that people there embrace the pleasures of life on the water. Yes, there are beautiful houses and sculpted lawns—but more than anywhere else around, there is a surplus of gorgeous boats. Here are Shelter Island’s three signature styles.


Shelter Island Runabout: This is the style a lot of young Shelter Islanders dream of owning one day. With its square transom and high bow, the Runabout looks like a long, lean version of a Downeast Maine lobster boat. Don’t be fooled, though: the Runabout can rip, topping out around 50 mph.

Often with motorboats, the wise move is to lay off the throttle in rough water. With a Runabout, you can actually double down. They’re known to cut through chop like a knife through butter. As the name suggests, the Runabout is an original Shelter Island design—of pretty recent vintage, actually. CH Marine, in Coecles Harbor, has been making them since the mid-nineties. Local boat lover Billy Joel is traditionally given at least partial credit for the design; there’s said to be a napkin somewhere with his original sketches on it. The classic style is 38 feet. 



Doughdish: Nathanael Greene Herreshoff (1848-1938) has many famous boats to his name. He’s one of the most accomplished yacht designers of all time, the brains behind a slew of America’s Cup winners and many a Gilded Age tycoon’s pleasure cruiser. Funny, then, that a kiddie design has proven to be one of his most enduring.

It came about in 1914, when some clients from Buzzards Bay in Massachusetts asked for a sailboat their children could handle. Youngsters loved the Herreshoff 12 ½ footer he came up with; more surprisingly, grownups did too. When the first fiberglass reproduction went on sale in 1973, it was rechristened the “Doughdish,” which sounds like duodici, Italian for ‘twelve.’ Legend has it this was an Italian nanny’s name for the original, and it stuck. Sailors of all ages and skill levels have flocked to these stable, comfortable boats ever since. The Shelter Island Yacht Club has one of the largest Doughdish fleets in the east. On summer Saturdays you’ll see members out racing them in Smith Cove. 



Gentleman’s Etchells: The racing sloop known as an Etchells came about as a result of a 1965 building competition.The “Gentleman’s Etchells” was born years later, in the nineties, when sons of North Fork boatmaker Anders Langendahl decided to do some tinkering. Among other things, they stripped one of these 30-foot day sailers of technical bits and added handsome teak benches and toe rails.

Fast and elegant, the modified racer is a relatively recent arrival in Shelter Island, where it’s become a hit with the Yacht Club crowd. Though simplified, it’s
definitely not a beginner’s boat.