At the Vineyard Cup awards ceremony Sunday, which followed three days of spirited racing in Vineyard waters, it was a Nantucketer who took the top prize in the classic division.

Wendy Schmidt claimed first Dana Family trophy with victory in classic division. — Steve Myrick

Wendy Schmidt and her crew sailed the magnificent Sparkman & Stephens-designed X-9 Santana to a second place finish on Saturday, and was first in the pursuit race Sunday She claimed the first Dana Family trophy, a new perpetual trophy awarded to the classic division winner.

Ms. Schmidt was also awarded a permanent trophy, a silver bowl, which was immediately filled with a rum libation for her to sip.

She said the 55-foot sloop built in 1935 was just completely restored and refitted.

“She’s only been back in the water for six weeks,” she said. “We’re thrilled to see how Santana performed.”

Other overall winners, according to preliminary results posted on the Sail MV website, included William McCullough, sailing in the catboat and Bella class with Rosalee.

Charlotte, owned by Nat Benjamin. — Steve Myrick

Class 1 saw a familiar winner. Bob Lurie won all three races over the weekend regatta aboard Mischief, an Alerion 26.

In Class 2, Ruse, a Swan 44, was best overall with a win Friday and second place finishes Saturday and Sunday.

In the Spinnaker division Francis Satula’s Soma Holiday took top honors with first, second, and fourth place finishes.

The Vineyard Cup regatta kicked off Friday afternoon with a bit of a surprise: 15 to 20 knots of wind. Over the past two years, competitors struggled with very light air, and many recorded DNF (Did Not Finish) because they couldn’t sail the course within the allotted time limit.

But the stiff breeze wasn’t the biggest surprise of the 11th annual regatta, which is a benefit for Sail Martha’s Vineyard.

Vineyard Cup competitors sailed in 15.4 mile course on Saturday. — Steve Myrick

At the annual benefit Seafood Buffet and Auction the evening before competition got underway, Newport Shipyard owner Charlie Dana 3rd drew sustained applause when he announced he would donate Thor, his family’s exquisite 55-foot wooden yawl, to Sail MV.

Mr. Dana, who comes from a family of noted philanthropists, told the crowd his family had many happy summers of sailing aboard Thor.

“She’s a very special boat,” he said. “We salute what you all do here. We love what you’re doing.”

Thor is a valuable boat, designed by Philip Rhodes and built by Abeking and Rasmussen Shipyard in Germany. She was on display with a dozen other classics at Tisbury Wharf.

Fifty-five foot yawl Thor, donated to Sail MV by Newport Shipyard owner Charles Dana 3rd. — Steve Myrick

Sail MV is working now to establish a plan for Thor that will best benefit its sailing and educational programs.

Also at Thursday’s dinner, Sail MV awarded the Walter Cronkite award to historian and writer Nathaniel Philbrick, author of In the Heart of the Sea and other books with themes of maritime history. The Cronkite award is given annually to someone who demonstrates commitment to the Sail MV organization and its mission. In accepting the award, he talked about how history shapes a community.

“It’s about keeping the history that created your community alive, and you guys are doing that,” Mr. Philbrick said. “Sail Martha’s Vineyard is a huge reason why, keep it going, keep supporting it.”

On the water Friday, the wind challenged the fleet, forcing a few crews to drop out because of equipment failure while others struggled to set spinnakers on the downwind leg back toward the Island.

A parade of sail graced the harbor on Saturday morning, and the classic division was first across the line. The fleet sailed a 15.4-mile course around the three major shoals between Martha’s Vineyard and the mainland. The first leg was to Hedge Fence in the middle of Nantucket Sound, further northeast to L’Hommedieu Shoal, back toward shore and around Squash Meadow, then back up State Beach to the finish line in Vineyard Haven Harbor.

Three days of competition come to an end; 'til next year. — Steve Myrick

Sunday’s pursuit race kicked off at 10:30 a.m., just after morning showers gave way to gray skies. The fleet talked up the first leg to a buoy off Falmouth, and then nursed a dying breeze back to Vineyard Haven Harbor, with the competitors bunching up at the finish line.

Spirited post-race parties under a tent at Tisbury Wharf kept the fleet well-fed and entertained after each day of racing.

Sail MV executive director Brock Callen wrapped up the race weekend with an invitation to return for the 2017 Vineyard Cup.

“Can’t wait to see you next year,” Mr. Callen “We’ll try to make it bigger and better.”