Tactical dilemmas made it anybody’s race to win with a mile of water to go.

As many as 25 boats gather in Vineyard Haven Harbor on Thursdays and Sundays for fun and bragging rights. — Steve Myrick

On the final leg of the Holmes Hole Sailing Association preseason tune-up race, held over the past weekend, competitors faced a bewildering combination of current, wind, water depth and sailing rules. With the tide pushing west so hard it laid big navigation buoys over at an angle, and an easterly breeze building steadily, the variables that went into tactical decisions were enough to weaken the sea knees of any sailor.

Tack out in Vineyard Sound, sail a longer course but avoid the stronger shoreline current? Slip under West Chop, risking shoal water to catch a wind shift or favorable eddy toward the final mark? Take advantage of the strengthening breeze and sail a shorter distance, but barge into the strongest part of the adverse tide?

Aboard King Kiwi, a Sabre 38, skipper Irving Gates and crew decided on the first option, sailing a longer course, but against weaker current.

With a collegial potluck dinner Saturday night, and the tune-up race Sunday, the Holmes Hole Sailing Association begins another season, striking a balance of hot competition and warm friendship. Every Thursday evening and Sunday afternoon until Labor Day, as many as 25 boats will meet in outer Vineyard Haven harbor to race for fun and bragging rights.

A complex handicap system gives every crew a chance to win, and rewards improvement and participation as much as sailing skill. With no barrier to participation other than a modest $60 annual fee, the organization draws a diverse group to the starting line.

“The best part about Holmes Hole is it’s open to everybody,” said Roger Becker, who is a familiar sight skippering his red C&C 24 Gloria around the course in many of the season’s races. “People can get any old boat and show up, and they’re welcome.”

Mo Flam, who sailed his Alerion X28 Penelope to the season championship last year, agrees.

Sailing aboard King Kiwi. — Steve Myrick

“It’s such a diverse group of people,” Mr. Flam said. “You get the high performance boats, down to things people pick up used. “You have CEOs and carpenters out there sailing together.”

The Holmes Hole Sailing Association began in 1976, dreamed up by some of the Island’s best local sailors as a way to skip the yacht club culture, restrictions and expense and create a competitive racing series. Frank Jewett, Pat West, Hugh Schwarz, Harry Jones, Tom Hale, Tom Mendenhall, Joe Low, Hank Scott and Bud Haven were among the early organizers, according to a history of the organization.

Another of the early movers and shakers was George Moffett, who is honored each year as the namesake of the season ending competition, called the Moffett Race. Over the years, the Moffett cup has grown in stature and legend, and it is a fiercely desired trophy for local sailors. In recent years the race, held the weekend following Labor Day, has drawn 50 to 60 entries.

None of it happens without many hours of volunteer work. The Vineyard Haven Yacht Club provides invaluable support, including a committee boat to organize the start of the races, and a gathering space for mostly-true stories to be told after the racing is done.

In boat racing, handicaps come in the form of time. A boat that is designed for racing, with high performance equipment and sails, gets a low rating. A family cruising boat, designed more for comfort than speed, gets a higher rating, and is assigned an amount of time to subtract from the actual elapsed time sailed around the course. On “corrected time,” the two boats are theoretically equal, and sailing skill determines the race winner. The association’s chief handicapping guru is Mr. Becker, who is lauded by other members for the amount of time and detail he puts into handicapping more than 40 boats which participate. He adds another element to handicapping, a massive number crunching exercise that compares actual times in actual races for every boat in the fleet. It is entirely an objective process, which creates a system where you must improve over previous races to overcome your handicap. Conversely, if you have a bad year, you will have a little bit easier time in future years. “The better you do, the harder your rating becomes,” said Stephen Besse. Mr. Besse, who sails his J/120 Apr é s, is an accomplished racing sailor who was a three-time state champion in his junior sailing days. “Everybody’s going to win their share of the time,” he said, adding with a laugh: “It may be a little bit tough for those of us who think we should win all the time. To me it’s just nice to get out on the water and do the best you can.”

Gloria in all her glory. — Steve Myrick

“I think that’s the best part about it,” Mr. Becker said, “by eliminating the business of proving you’re the best sailor, but giving you an opportunity to compete on a friendly basis.”

Crews who win the season championship are assigned a penalty of 15 seconds per mile for the following season, which makes it very difficult for one boat to dominate the standings.

Aileen, a custom-built Sparkman & Stephens 35-foot sloop, represents one facet of the diverse fleet. Owned by Comcast CEO Brian Roberts, a seasonal Vineyard homeowner, Aileen is one of the fastest boats in the in the harbor. Mr. Roberts is often at the helm, mixing it up with local sailors. “He obviously enjoys it because he’s out there competing,” Mr. Flam said. “I have a lot of respect for him. He could have a crew running a big yacht, and he’s out there sailing his boat himself.”

Mr. Roberts, at the helm all the way, won the tune-up race, with the best elapsed time and corrected time.

Finishing second on corrected time was Tom Welch aboard his J/100 Escape.

And King Kiwi? That decision to sail a longer course out in the middle of the Sound, but avoid the shoreline current was either lucky or smart, because King Kiwi made up a lot of ground to finish third of 11 boats overall on corrected time, and first of the eight boats in the B class.

“It was good to be sailing again,” Mr. Gates said.