A Wider Pool of Sailors

Founded in 1991, Sail Martha’s Vineyard continues to grow, offering programs for all ages. Its fundraising regatta, the Vineyard Cup, marks its fourth year July 17 to 19, offering the Island’s sailors a weekend of activities and races, as well as bringing in off-Island sailors and money.

On a breezy July day, a fleet of a hundred sailboats of many shapes and sizes gathers in Vineyard Haven, united by a love of sailing and racing. The harbor bustles with its usual mid-summer activity, and the diverse fleet dodges the Island Home and other vessels on their way to and fro. Out on the course, the skies are hazy as boats round a bell buoy serving as a mark, some with barking of orders and frantic cranking of winches, while others have sailors with glasses of wine in hand. In late afternoon, the competitors gather at the event headquarter’s tent in Owen Park, talking and laughing, and the beverages are more evenly distributed. Big boat racing is back on Martha’s Vineyard, and everything seems as it should, right down to the sunburned noses and polo shirts with popped collars.

Images of sailboats under sail are ubiquitous on the Vineyard, from postcards to stitched pillow-covers, but the only boat rides most of us take are in our cars tucked in the hold of a Steamship Authority ferry. The history and culture of the Vineyard drips with whaling ships and cargo schooners, yet sailing today is done simply for fun, mostly by the strata of Vineyarders with generous amounts of both leisure time and financial resources.

Sail Martha’s Vineyard battles this trend. With an impressive variety of programs for all ages – but focused on the Island’s youth – and an energetic and talented volunteer base, Sail MV is dedicated to celebrating, preserving, and protecting our Island’s maritime heritage.

But as any sailor can tell you, sailing requires money. So Sail MV created the annual Vineyard Cup regatta four years ago to raise funds for the program, as well as to provide a weekend of fun. Last year 106 vessels sliced through waters all around the Island, in what Sail MV dubbed “serious racing and serious fun.” Sail MV’s program director, Brock Callen, a Chilmark resident, says this year’s moniker is, “What a regatta ought to be! Fun and affordable.” The main events are on Saturday and Sunday, with sailboats racing in competitions more friendly than fierce, and plenty of celebrating at evening parties in Owen Park on Vineyard Haven harbor.

“The Vineyard Cup is different like the Vineyard is different.There’s a lot of camaraderie on the beach. It’s laid-back, but not so laid-back that it’s sloppy,” says Sail MV Vice President Peter McChesney, who lives in Tisbury. Fun doesn’t preclude competition though, Peter says: “If your goal is to go fast, you’ll have competition.” With more than a hundred sailboats competing, it can get tricky. Most of the several classes of larger boats sail from busy Vineyard Haven harbor into the Sound. Meanwhile boats like Herreshoff 12 1/2s and Sunfish, which are smaller than the twenty-two-foot minimum, race in Menemsha Pond. The Edgartown Yacht Club races for one-designs are also part of the weekend, along with distance-windsurfing races out of Vineyard Haven harbor.

In addition to races for divisions of several handicapping systems, the Vineyard Cup offers competition for one-design fleets, such as the Nonsuch. Last year eighteen Nonsuch boats, featuring both experienced and first-time racers, competed largely against each other, using the Cup as a rendezvous weekend; many stayed in the harbor well into the next week. Designed to be comfortable and easy to sail, the Nonsuch vessels (similar to cat boats) are popular with older sailors. “The folks who finished sixteenth had as much fun as those who finished second or third,” notes Peter, who sailed aboard the fourth-place vessel Raven with Art and Carolyn Spengler of West Tisbury. The Nonsuchs will return this year in larger numbers, and Sail MV expects more fleets will use the Vineyard Cup as a get- together weekend.

Despite economic headwinds, early indications are that the 2009 Vineyard Cup will see continued growth, after more than doubling in size from 2007 to 2008. Brock credits the popularity of the regatta to an emphasis on affordability as well as fun, noting that a thirty-two-foot boat can race for a $125 entry fee, and a $40 bracelet buys entry to three evenings of catered parties. Brock credits the low fees to the regatta’s sponsors, including Island businesses such as The Black Dog Tavern, Vineyard Vines, and Martha’s Vineyard Shipyard. But to support the growth of the Vineyard Cup and Sail MV, Brock says, “We’ve had to reach beyond the shores of this fine Island.” That effort has secured national sponsorship from Men’s Journal magazine, Nautica Oceans men’s fragrance, and sailboat builder Alerion Express, among others.

The Vineyard Cup raises roughly 20 percent of the budget for Sail MV, which has taught about 2,500 Island children to sail since it was founded in 1991, and last year served a record number of more than 400 kids aged eight to eighteen. These are children who might not otherwise have access to a sailboat, a symbol of the Vineyard’s history and culture. And all Island children who participate in the sailing program, Brock stresses, do so for just the $40 annual membership fee.

The summer courses range from the introductory “Messing Around in Boats” class, to sailing in Optimists and 420s, to windsurfing. But Sail MV doesn’t stop on Labor Day; it continues year-round with a wide range of programs, like the Martha’s Vineyard Regional High School sailing team that Sail MV founded in 1995, and which gained varsity status in 2000. Today, still with Sail MV’s support, the high school team is a sailing powerhouse, with most of the skippers and crew having come through the summer program rather than the Island’s yacht clubs. Emmie Schreck, a senior from Edgartown, races with the team, and says that since she’s not from a sailing family, she wouldn’t have been able to learn the sport that she loves without Sail MV. “I’ve met a lot of terrific people, and the coaches have been very kind to me,” she says. “I’ve learned responsibility and commitment to the team.”

Also at the high school is the new Maritime Studies vocational program to give students a start on the skills needed to ease their entry into maritime careers. “How cool is it to teach kids how to earn a living on the water, locally?” says Sail MV President Peggy Schwier, who lives in West Tisbury.

Known for its youth programs, Sail MV also has activities geared to adults, including the long-standing races on Menemsha Pond and winter “frostbite” racing. Adult education, such as captain’s license courses and classes in diesel-engine repair, is also part of Sail MV’s curriculum, as is the opportunity to see and tour visiting vessels such as the schooner Spirit of Massachusetts, which last came to the Island three years ago. Sail MV even offers Rowing MV for adults, using the Island-made thirty-two-foot Cornish pilot gigs Grace and Cassie, often seen next to the ferry dock in Vineyard Haven.

The Vineyard’s boat-building tradition is important to Sail MV; its fleet includes the rowing gigs, and four flatiron skiffs recently built by Rick Brown at Far Cry Boat Shop in Vineyard Haven. The Cornish pilot gigs were a community effort: Nat Benjamin of Gannon and Benjamin Marine Railway Inc. designed the vessels, Ross Gannon oversaw and helped with the building, which was done by volunteers from the rowing team, and the Douglas family, of Black Dog fame, gave space at their Five Corners shipyard. “You don’t preserve and protect the Island’s maritime heritage by buying Boston Whalers,” says Brock – though he admits that Sail MV has some of those too.

Brock says that all this activity “takes up more hours in a week than actually exist.” He and his wife, Hope, are the only paid, full-time, year-round staff, so Sail MV relies heavily on volunteers. Brock repeatedly stresses the dedication and talent of the board of directors, the executive committee, the advisory board, and the dozens of other volunteers who do everything from raising funds to painting hulls. “The resources we have on this Island are unbelievable,” says Brock, rattling off prominent boat builders and pro racers and captains and pilots and mariners of all sorts who help Sail MV. At a dinner in April honoring the volunteers, Peggy Schwier stresses, “We couldn’t do what we do without each and every one of them.”

Peter McChesney, who grew up in Branford, Connecticut, and often visited the Chesapeake Bay in Maryland, illustrates a common thread among volunteers: “Growing up on the water was very special to me, and that’s why I’m doing what I’m doing.” Brock seconds that, recalling sailing from Marblehead with his brother: “We cruised all over the northeast.” Sail MV has now been around long enough that some of the first kids to go through the program have now come back as volunteers. “It’s the volunteer spirit: They circle back to help the team that gave them great skills and great experiences,” Brock says.

Volunteers aside, a program this large requires funding to match. “The biggest challenge we have is correlating our fundraising to our growth,” says Brock. The budget of roughly $440,000 comes from an annual membership drive and – in addition to the Vineyard Cup – events such as the Holiday Maritime Art Show in December, the Annual Seafood Buffet and Auction in July (on the 11th this year), and The Black Dog Winter Dinner and Lecture Series.

The explosive growth of Sail MV necessitates a fleet of eighty boats, and led it to partner with the Chilmark Community Center, where it now runs an up-Island sailing program in addition to the one at the main campus at Sailing Camp Park in Oak Bluffs. At this point, Brock says Sail MV is “maxed out on physical space,” and he sees yet another challenge in maintaining quality: “You can have all the money in the world, but quality is consistent with our maritime heritage.”

On the water at the Vineyard Cup, among the waves and sun and salt spray, thoughts of fundraising are overwhelmed by sailing strategy and tactics. The ‘08 Cup enjoyed fine sailing weather, with steady winds and moderate temperatures. Sunday featured a pursuit format, with staggered start times based on each vessel’s handicap, so that the first over the line would be the clear winner. The boats raced into the harbor in a pack, with Charlotte, Nat Benjamin’s new fifty-foot gaff-rigged schooner, taking top honors and earning the Bronze Lobster trophy at the awards party on Sunday evening.

Maybe on some future July weekend, a kid who took his or her first sail in a Sail MV Opti will hoist the Bronze Lobster. Sail MV classes can lead to serious racing, to a career, or just to a love of the water. Peter McChesney emphasizes the lifelong aspects of sailing, noting that it’s a sport where boys and girls, men and women, old and young can compete with and against each other. “Sailing,” he says, “is something you can take with you for a long time.”