Next weekend sailors eager to test their salt will head to Vineyard Haven to participate in the Vineyard Cup, the annual sailboat race that is also a fundraiser for Sail Martha’s Vineyard.

This year, the race will be held on July 12 and 13, with a rain date scheduled for July 14. 

In search of Vineyard bragging rights. — Mark Alan Lovewell

On Thursday evening before the race, Sail MV will host its annual seafood buffet to benefit the nonprofit, which was established in 1992 and continues to promote sailing and maritime activities to both kids and adults on the Island.

“Every dollar raised by any of these events goes straight to Sail MV,” said Andy Nutton, executive director of Sail Martha’s Vineyard.

The race, now in its 20th year, generates interest among every type of sailor, old and young, beginner or seasoned professional. Using a handicap system, the rules of the race allow for boats of all shapes and sizes to compete against one another.

“You have all these other boats out on the water,” said Mo Flam, a sailor who won the non-spinnaker division of the Vineyard Cup and has finished in the top three on multiple occasions. “That’s one of the great things about the Vineyard Cup, is that there’s all kinds of boats.”

The race will take place in Vineyard Sound just as it has in the past. The official race route will be announced as the start date nears to ensure that the weather and the route provide the best opportunity for racing.

For Mr. Nutton each day on the water offers a new experience. 

“The power system is something you can’t see, you can only feel, and the medium in which you’re traveling through is dynamic,” Mr. Nutton said. 

Sailing is not like Formula 1, he added. “You can’t just press the overtake button.”

Race is for all ages. — Ray Ewing

For most sailors, being on land doesn’t hold the same excitement as life on the water. Its not they they dislike terra firma, rather, they prefer trying to understand the world of water more intuitively.

“I’ve lived on the water for almost 16 years,” said Robert Harding, known around the water as Bear. “It still gives me a thrill to have the sails up and be cruising through the water, knowing that it’s just the power of the wind.”

To onlookers watching from the safety of the shore, it may look odd seeing a bunch of boats of various shapes and sizes jockeying for position along the Vineyard Sound, but for sailors pitted against one another the experience is highly kinetic. Frequently, racing sailboats boils down to a game of inches, and micro-adjustments can make all the difference.

And according to Mr. Flam and Mr. Harding, mistakes will always be made.

“Of course, making the fewest amount of mistakes, that’s paramount, and getting a little lucky helps,” Mr. Harding said.

“And you just move on, you know,” said Mr. Flam. “It’s just a fun way to spend a day on the water.”

For all three men, the race’s connection to Sail MV gives it a deeper significance. According to Mr. Nutton, Sail MV raised $200,000 last year to help keep the program free. The organization also helps people looking to pursue education and careers in the maritime industry. It is even responsible for facilitating funding for Martha’s Vineyard Regional High School’s sailing team. 

The Vineyard Cup is now in its 20th iteration. — Ray Ewing

“I believe strongly in the Sail MV program and being able to see young people and members of the community have an opportunity to go sailing,” said Mr. Harding. “There is pleasure from being on the water as well as opportunities for a career in the maritime field.... I feel very fortunate to have landed on Martha’s Vineyard, where so many of the people who live here are in some way connected to the sea.”

Mr. Nutton said that the story being told during the Vineyard Cup is the same one being told at Sail MV. It is a story of patience and fortitude.

“The cadence of the sea is a beguiling thing,” said Mr. Nutton. “It takes a little time to understand. You can’t rush it.”