The 11th annual Vineyard Cup is set to sail this weekend, with three days of racing in Island waters. By mid-week, nearly 90 boats had signed up to participate. The annual Seafood Buffet and Auction, the year’s main benefit for sponsoring organization Sail Martha’s Vineyard, precedes the sailing competition on Thursday evening.

Five separate classes of sailing vessels will compete, including a classic division showcasing many of the wooden boats from the Island. Competitors range from weekend catboat sailors to high-tech racing sleds with professional crews. The first race begins Friday afternoon at about 1 p.m. The start and finish of all races can be seen from vantage points on East Chop, including Eastville Beach.

On Saturday morning at 8:45 a.m., classic and PHRF divisions will form a parade of sail around the inner Vineyard Haven Harbor. The first race on Saturday is for the classics, beginning at 10 a.m.

According to Weather Routing Inc., the official forecaster for the regatta, winds are expected to be light and variable on Friday afternoon, but freshen and steady from the southwest on Saturday and Sunday, as a cold front moves through the region.

With a heavy emphasis on fun, post sailing parties are planned each evening at the race village on Tisbury Wharf.

To mark its 25th year of free sailing programs for Island kids, Charlie Dana will establish the Dana Family Cup, a perpetual trophy to be awarded to the overall winner of the Vineyard Cup competition.

At the benefit event, the organization will present the Walter Cronkite Award to Nathaniel Philbrick, the Nantucket-based writer and historian who has written 13 books about maritime history. The event takes place at Tisbury Wharf on Vineyard Haven Harbor.

“Walter Cronkite was a founder of Sail MV, an honorary director, and was there to help us over the years,” wrote Peggy Schwier, president of the Sail MV board of directors, in her letter to Vineyard Cup participants. “He attended many a Seafood Buffet and Auction. He was our honorary commodore at our first Vineyard Cup, in his yacht Wyntje. He had always said that our organization was a quintessential Martha’s Vineyard organization, home grown and home supported.”

Proceeds from the benefit dinner and auction, as well as the race, go to support Sail MV programs.