Island windsurfer Nevin Sayre is heading back out to sea to battle the winds and currents around the Vineyard for a good cause. 

Mr. Sayre was the first person to sail around the Vineyard on a wing foil last year, taking up the challenge to raise money for Martha’s Vineyard Community Services. Last summer he raised more than $30,000 for the Island nonprofit.

This time he wants to nearly double that amount by trying to raise $1,000 per mile for a total of $55,000, The sail is set to occur sometime between August 15 and Sept. 15. 

A resident of Vineyard Haven, Mr. Sayre was inducted into the Windsurfing Hall of Fame last year.  

This year's goals are bigger.

Ray Ewing

This year's goals are bigger.

Ray Ewing

Mr. Sayre said Community Services means a lot to his family, and that his mother Harriet Hart Sayre served as board member.

“They are the umbrella network of all the important things, from childcare to substance abuse to all kinds of everything,” Mr. Sayre said. “For me and our family, they are the core to providing social services for the Island.” 

The challenge of navigating by sea the 55 miles of Vineyard shoreline was also appealing.  

“On some parts of the Island the wind is blowing onshore, and other parts it’s offshore. Some places it’s much stronger than other parts,” he said. “You will be against the current half the time that you’re out there. So handling that and deciding which way you go and where you start from is all a challenge.” 

Wind foiling also offers a greater mental challenge compared to windsurfing, according to Mr. Sayre.  

“When we went around the Island on windsurfers, if your mind wandered you weren’t going to fall off the board or anything,” he said. “But on a foil, you really have to concentrate all the time to balance on the little foils that you’re riding on. I was the most exhausted I’ve ever been mentally after last year’s challenge.” 

Community Services marketing director Karen Kuhlman said the organization is honored to have Mr. Sayre undertake this physically arduous trek for them. 

“It’s always good to have fundraisers that are community based,” she said. “In Nevin’s case, it’s nice that he is from the Island to bring in the support of people he already knows and grew up with. It’s also nice to bring his connection with Community Services.”

This is not the first event Mr. Sayre has organized an event for the benefit of Community Services. From 1988 to 2018, he spearheaded the MV Windsurfing Challenge, gathering sailors from all over the world to compete and fundraise for Community Services. 

“I feel so fortunate to be able to, after all these years, still be able to do it,” he said. 

Though he has sailed all around the world, his home waters mean the most to him.  

“There are admittedly other great places where winds are arguably better, but this is where I’m from and this is where I live,” Mr. Sayre said.