Competitors are ready to set sail in the 41st Moffett Cup Race Saturday morning, the annual end of season competition sponsored by the Holmes Hole Sailing Association. The race, divided into two divisions, gets underway shortly after 11 a.m. off East Chop, near Eastville Beach.

A total of 33 skippers have signed up their boats and crews to compete, a bit fewer than past years when the fleet totaled as many as 45 boats.

Among those entered is Stephen Besse, who sailed his J/105 Apres to victory in the past three Moffett Cup races.

The feat is all the more noteworthy because of the unusual rules of the Moffett Cup, which heavily handicap each year’s winner in the following year’s race.

Mr. Besse, who was nationally competitive as a junior sailor, said he was the beneficiary of the right boat in light winds over the past three years, which, along with some very good sailing, allowed him to overcome the stiff handicap penalties.

He was genuinely chagrined to win last year, and said it would be better for the race if another competitor took line honors, but he is back for another try this year.

“It’s kind of hard for him to slow down,” said Holmes Hole Racing Association commodore Mo Flam.

Mr. Flam was busy this week meeting with some of the Holmes Hole regulars who work out handicaps for the fleet. If the weather forecast holds true, Mr. Besse will have a tougher time of it this year.

“The prediction is for 15 to 20 knots,” said Mr. Flam. “That would be great, it would definitely help some of the bigger, heavier boats, especially the classic boats that compete.”

Others who look very competitive in this year’s Moffett Cup include Jerry Goodale skippering his Catalina 34 Sienna. Mr. Goodale took overall honors in the season series for division “A” in the summer long Holmes Hole race series.

Alan Wilson, in his Stuart Knockabout Altius was best of the season in division “B.”

Tom Wescott in his Alerion 28 Tamu, Mr. Flam in his Alerion 28 Penelope, and Phil Hale in his J/100 Tango also look to have a big chance based on good showings during the regular season.

Another threat is Frank Sutula, skipper of the Hanse 355 Soma Holiday, who tied for the win in his division of the Edgartown Yacht Club Round the Island Race this year.

The Moffett Cup is always a good combination of camaraderie and competition. At stake is a lovely half model trophy for the fastest boat on corrected time. But the real trophy is nothing less than bragging rights for the Vineyard Haven waterfront through the long winter when boats are sitting high and dry and the only thoughts of sailing are for the season to come.

“The Moffett is a race where you get all types of boats together,” Mr. Flam said. “This is the time when everybody comes together and has one great finale on the water.”