Following two days of spirited racing in Vineyard waters, and one day of canceled racing, sailors taking part in the 14th annual Vineyard Cup regatta joined ranks on Sunday for an awards ceremony at the race village on the Vineyard Haven harbor.

The regatta is a fundraiser for Sail Martha’s Vineyard, a nonprofit dedicated to introducing sailing to Island kids since 1992.

Among the class winners was Penelope, owned by Mo and Pam Flam of Vineyard Haven. Built in 2010, Penelope is a 28-foot Alerion Express. Placing first on Friday and second in the division on Sunday, she took home the Vineyard Cup Trophy, which is granted to the boat with the best cumulative, corrected finishing places. She also won the PHRF non-spinnaker first division.

The regatta is a fundraiser for Sail MV, a nonprofit dedicated to introducing sailing to Island kids since 1992. — Louisa Gould

Mr. Flam credited his victory to “some good tactics, good steering, a good crew and a little luck.”

He also said he had some friendly competition from a handful of other Alerion Expresses that were in the race, such as At Last and Providence. At Last finished third in the non-spinnaker first division.

Winning the PHRF non-spinnaker second division was Kitty Hawk, owned by Winthrop Sanford. Kitty Hawk is a Nonsuch 33, built in 1989. She finished just ahead of Starfish, piloted by the MVRHS sailing team, which won the Cape and Islands Fleet Racing Championship earlier this season.

Aprés, owned by Steve Besse, won the PHRF spinnaker division, and Sonny, a 53 foot Sparkman and Stephens sloop captained by Craig Venter, won the Classic Division. Sonny was presented with the Dana Family Cup and also took home the perpetual trophy, a polished wooden block that can be mounted onto the boat.

Sonny was built in 1935, but the oldest boat in the race was Malabar II — a 43-foot 3-inch double gaff schooner built in 1922.

Due to lack of wind on Saturday, no prizes were awarded for the catboat division. Many boats were becalmed just outside the harbor and unable to push through against a strong current.

Keeping it close. — Louisa Gould

“The wind came beating back out of the west,” said Ross Gannon, who raced aboard Sea Cloud. “Less than one-quarter of the fleet made it to the first marker, and everyone else got swept away with the current.”

Saturday was the only race for the catboat division, and many of the sailors were frustrated that they weren’t able to participate in the event.

“Racers like to race, I understand that,” said John Kettlewell, executive director of Sail MV. “We were all disappointed, but it was probably the right decision . . . most of the boat’s wouldn’t have completed the race and a DNF [did not finish] would have hurt the scores.”

Many declared the highlight of the weekend’s regatta to be the pursuit race. In this race, organizers of the event staggered the starting times of the boats based on a calculated handicap, the aim being to have all boats finish at the same time.

According to race director Ellen Pesch, the entire fleet rounded the Nun 4 red mark into the harbor within 15 minutes of each other. The 37 boats in the race were led by Sonny and Malabar II.

All proceeds from the Vineyard Cup go to supporting Sail MV programs. This year, Mr. Kettlewell explained, the money will specifically go towards a new initiative called Sail Mobility MV — a program to help get disabled people on the water.

“Part of our mission is to make on the water experiences available to everyone,” he said. “We provide sailing training to over 500 kids each summer, and we hope to keep expanding that number each year.”