In 2024, Nevin Sayre, a hall of fame wind surfer from Vineyard Haven, nearly died while kite surfing along Sengekontacket Pond. 

He was launched 20 feet into the air and then slammed into the water below. Mr. Sayre was knocked unconscious on impact, but was saved by onlookers who witnessed the incident.

Despite the near-death experience, Mr. Sayre would not be deterred from harnessing the power of the wind. Sometime in the coming weeks, Mr. Sayre will attempt to circumnavigate Martha’s Vineyard on a wing foil to raise money for Martha’s Vineyard Community Services.

He will have to cross over 55 miles in total. His goal is to raise $1,000 for each mile. Already, he has raised more than $30,000. Last year, Mr. Sayre raised more than $100,000. 

“This is the organization that impacts Islanders more than any other in terms of actual needs,” said Mr. Sayre. “Every social service comes under the umbrella of Martha’s Vineyard Community Services.”

The first year Mr. Sayre attempted the ‘Round the Island Challenge, he wasn’t even sure it could be done in a single day. That was almost 20 years ago. Since then, Mr. Sayre has travelled around the Island by wing foil a couple of times. 

“I’ve done it twice now on a wing foil,” said Mr. Sayre. “Which is good because I’m a little less nervous about it, but it really depends so much on the wind and the currents.” 

During each circumnavigation, Mr. Sayre pays particular attention to the shifting wind and current as well as a minefield of seaweed that forces him to stop periodically to clean the hydrofoil bolted to the bottom of his board.

When Mr. Sayre spoke to the Gazette, he had just finished a 25-mile training session to prepare for his upcoming endeavor. At the moment, it doesn’t look like the weather will provide a good window until the first week of September, said Mr. Sayre. But he doesn’t mind; this only gives him more time to train, study the weather and prepare the team that will follow him in a patrol boat.

In an effort to broadcast the attempt, MV Community Services will display in real time Mr. Sayre’s positions as he sails around the Island. 

“I heard from people all over the world who were following last year’s progress,” said Mr. Sayre. “It was kind of cool.”