For Miles Wolff, growing up with the Island sailing scene served as a launchpad to his college career on the water. This fall, he captained his team at the College of Charleston to win the Kennedy Cup on Nov. 2.
For Miles Wolff, growing up with the Island sailing scene served as a launchpad to his college career on the water. This fall, he captained his team at the College of Charleston to win the Kennedy Cup on Nov. 2.
The Kennedy Cup, held annually at the Naval Academy in Annapolis, is the national collegiate championship for keelboat sailing.
Mr. Wolff is a former member of the Martha’s Vineyard Regional High School sailing team, graduating in 2022. He is currently a senior at the College of Charleston.
“I found my passion for sailing at a very young age, and was very fortunate to be on the Island, seeing that there’s so many different outlets for sailing,” he said during a phone interview with the Gazette. “The sailing moments at a young age definitely morphed me into who I am today and the opportunities that I was afforded with.”
He credits Sail MV, a nonprofit organization on Island that provides sailing opportunities and maritime education, for kickstarting his love for the water.
Miles Wolff with the hardware.
Miles Wolff with the hardware.
“SailMV was really awesome to be a part of as a kid,” Mr. Wolff said. “They sponsor the MVRHS team with their facility down on the lagoon and allow for that whole program to be alive.”
In high school, he learned how to sail primarily in dinghies. He spent his first year sailing at St. Mary’s College of Maryland in dinghies, before transferring to Charleston, where he started sailing in keelboats. While dinghies typically hold one to four people, keelboats are manned by eight to ten people.
“It was a huge learning moment for me to have to form a team and lead a team of eight people who are all important in their own way, that do their own task on the boat. That contributes to the overall success of the boat,” he said. “If one person messes up, it can lead to disaster amongst the other seven people on the boat, so it’s always really neat to be able to work together with those eight people and make something happen as one unit.”
The Kennedy Cup is one of three main events in the fall collegiate sailing season. It is the second time Mr. Wolff has participated and the first time he has won the championship. As captain, he has enjoyed figuring out how to lead a team.
“It was an interesting challenge for me to find myself, to fit in that position and really understand how I wanted to lead the team,” he said. “It just felt really good to close out my senior year as a captain and to win this trophy with such a such an awesome team.”
The teamwork aspect of sailing is the most satisfying for Mr. Wolff.
“We finish a race, we win a race, and it’s just like the whole boat lights up, and it’s really neat to see everybody come together and accomplish one goal as if we were one person on the boat,” he said.
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