Blasting Around Nantucket Sound - The Vineyard Cup

In the early 1990's, the sport of sailing was in trouble on the island of Martha's Vineyard. If you were not lucky enough to own a boat, few avenues existed for those looking to get out on the water. Only the stirring sight of the schooner Shenandoah gliding in and out of Vineyard Haven Harbor served as evidence of the island's rich maritime past.

Vineyard Haven at dusk. Shenandoah lies at anchor.

Luckily, all of that was about to change. Since its founding in 1992, Sail Martha's Vineyard has provided a much-needed spark. With a mission of reconnecting the people of Martha's Vineyard with the ocean, it's programs have continuously expanded for the last two decades. These days, Sail MV proudly offers (among other things) a thriving summer program for kids, a varsity high school racing team, weekly adult sessions, and, as an annual signature event, the Vineyard Cup Regatta.

While the Roadshow only had three short days to take everything in, we tried our best to see it all. Tucked away in an idyllic corner of the Oak Bluffs Lagoon, the Sail MV junior sailing program operates out of a refurbished fishing barn. There, in the shadow of tall trees and scenic hills, island kids can start their lifelong relationship with the water without any fear of choppy seas or marine traffic. It really is an incredible spot. Led by a merry band of Irish and American coaches, these kids truly learn how to enjoy sailing for its own sake, as evidenced by the many hours of laughing, yelling and splashing that took place onboard Optis, Capris, 420s and US SAILING Roadshow O'Pen Bics. However, these kids are also given a clear path towards racing through the middle and high school teams, should they choose to follow it.

Above: The mighty Black Dog Tall Ship Alabama heads for the line. 

Below: Preparing for a start at the Vineyard Cup onboard the Morris 42 Jinji.

Our final two days were spent enjoying what was easily the most beautiful, amiable and well-organized big-boat regatta either of us has ever been a part of. Major credit goes out to the Sail MV Staff, led by Brock and Hope Callen, for attracted upwards of 70 boats and an incredible 24 major sponsors (And I mean major, with the likes of Men's Journal, AT&T, The Black Dog, Samuel Adams, Revo, and others) to the Vineyard Cup. The courses led the fleet all over Nantucket Sound each afternoon, from Vineyard Haven, over to the shores of Cape Cod, and past Oak Bluffs on the way back. Even better, the breeze cooperated magnificently each day, providing close, exciting racing amidst white-capped waters and a stiff current. Hurtling up the Sound, perched on the windward rail, with your legs dangling high over the water, it's easy to reconnect with your innate love of sailing. Life just doesn't get any better.

The Sail MV Junior Program

It seems clear that thanks to Sail MV, the lucky islanders of Martha's Vineyard will never again be in danger of losing the intimate relationship with the ocean that helps to define this special place.

-Will

Post-regatta shoreside festivities