Champion sailor Nevin Sayre of Vineyard Haven notched a new record Friday when he became the first person to wing-foil around Martha’s Vineyard.

The six-hour, clockwise trip, which began and ended at Inkwell Beach in Oak Bluffs, was a fund-raiser for Martha’s Vineyard Community Services.

“We raised over $20,000, and money is still coming in,” Mr. Sayre told the Gazette Monday.

Mr. Sayre has windsurfed around the Island many a time. From 1988 to 2008, he hosted the Round the Vineyard Challenge, an MVCS benefit that drew up to 40 board-sailors each September. That event was a major undertaking, he recalled.

Journey took over six hours to complete. — Chace Lewis

“I’d spend months organizing checkpoints and spotter planes,” said Mr. Sayre, who was inducted into the Windsurfing Hall of Fame earlier this year.

“What’s different about doing it now is that it was just me ... and I could choose the day,” he said.

Friday morning, Mr. Sayre made his choice.

“We had a northeast, gentle breeze [that was] forecasted to build, and the currents were reasonable and it was a beautiful day, so I thought it was worth a try,” he said.

Accompanied by friends in a sturdy support boat, Mr. Sayre set out from Oak Bluffs at about 9 a.m. for what he expected would be about five hours on the water.

He was prepared for some challenges on the way.

“The current was going to be against me at Wasque, where the current always throws up big waves against the wind, and the current would be starting to switch against me in [Vineyard Sound] around 2 o’clock,” Mr. Sayre said.

“But I actually went from Inkwell and around Chappquiddick to Katama in really good time, got through Wasque without a lot of drama, and things were looking good,” he said.

Then the wind dropped, leaving Mr. Sayre without enough breeze to propel his carbon-fiber wing and hydrofoiling board along the Island’s south shore. Fortunately, he said, there was a good sea swell running westward.

“With a hydrofoil, you can pump your legs and stay up on the swell — but it’s a lot of work,” said Mr. Sayre, who managed to stay on his board all the way to Aquinnah with the hope of catching a fresh breeze after he rounded the Gay Head Cliffs.

“I figured the northeast wind would be blowing down the [Vineyard] Sound and everything would be golden,” he said.

Just after noon, disappointment struck.

“I rounded Gay Head, and there was no wind,” said Mr. Sayre, who floated offshore as his support boat hovered nearby.

“I’m halfway between Gay Head and Cuttyhunk, sitting on my board. It was seriously in question if I was going to make it,” he said.

“I was praying to my mom for wind,” added Mr. Sayre, whose late mother Harriet Hart Sayre was a devoted Martha’s Vineyard Community Services volunteer, president of its board and the inspiration for her son’s sailing fundraisers.

After about an hour of floating on his board, Mr. Sayre got enough wind to continue his journey.

“It was a beat [upwind sail] from Aquinnah to East Chop, as expected, but there was enough power so I could make my way,” he said.

By the time Mr. Sayre got to West Chop, an hour behind schedule, the current was against him on the Island side of Vineyard Sound.

“I stayed outside [offshore],” he said, noting that the current switches later on the Cape Cod side of the sound. “I went almost to Woods Hole, to Nobska... and then was able to get to Inkwell, after six hours and nine minutes."

“I was toast. I could barely stand that night. My legs were like noodles,” he added. “It was a little more epic than I intended.”

To donate, visit mvcommunityservices.org.