Miles Wolff, a 21-year-old Island-raised sailor and Martha’s Vineyard Regional High School graduate, is making waves at the College of Charleston in South Carolina, serving as the senior captain and tactician for the Cougars Division I offshore sailing team.
Earlier this month, Wolff led his team to defend its national title at the Kennedy Cup, edging out the U.S. Naval Academy to take one of the most prestigious cups in collegiate sailing for the second season in a row.
The back-to-back national championships marked the first-ever consecutive title defense in history for the College of Charleston’s sailing team, and their eighth Kennedy Cup claim.
“I’d love to express how much of a privilege it was to be a part of a team who has won this trophy eight times now, but never back-to-back,” said Wolff in an interview with The Times.
The Kennedy Cup’s keelboat national championship sailing regatta took place on Nov. 1 and 2 at the Naval Academy’s Robert Crown Sailing Center in Annapolis, Md., and welcomed the nation’s top 10 collegiate programs to compete through six total races. Aboard identical 44-foot, 35,000-pound keelboats provided by the Navy, Wolff’s team finished the weekend with 17 points to the Navy’s 19, securing the Inter-Collegiate Sailing Association’s (ICSA) offshore national championship.
“[Winning the national championship] felt incredible –– there was definitely a lot of pressure going into this event,” said Wolff.
As the tactician and captain of his team, Wolff is positioned at the back of the boat alongside the helmsman. His job consists of trimming the mainsail to adjust and control the boat’s speed, as well as calling all the tactics throughout the race, foreseeing any maneuvers the team may need to make. But for Wolff, his love of offshore sail racing is born out of the agency needed of the whole team to achieve a desired goal.
“Nothing can get done without the work of the entire team,” said Wolff. “What I really love about the sport is that it’s a cool feeling to be the master of your own destiny, creating your own luck with where you want to be on the course.”
During his time on-Island, Wolff primarily sailed dinghies, which have a two-man crew. Transitioning to an offshore team in college, with larger boats and an eight-person crew, Wolff developed an appreciation for team-based sailing.
“I really love it for the team aspect. I grew up sailing in dinghies when it was just me and one other person; joining the offshore team gave me a unique perspective on how to work with a team effectively,” said Wolff. “If all eight people on board aren’t working together and there isn’t that camaraderie, nothing would happen. It’s a unique opportunity to build a team and lead eight people into successful situations.”
Teamwork was instilled early into Wolff’s sailing career. Wolff has been sailing his entire life, but his passion for the sport was largely developed from the age of 5, sailing at the Edgartown Yacht Club and later competing for the MVRHS SailMV team, coached by Andrew Nutton and Andrew Burr.
“I was super, super fortunate to be involved in those programs,” said Wolff. “I credit them with any success I was afforded in college, because they really taught me what it took to sail at a competitive level and be a leader.”
At the Kennedy Cup earlier this month, Wolff’s team was in second place, down by two points to the Navy’s Midshipmen, with only a couple of races remaining. The turning point came at the start of the fifth and second-to-last race. Charleston needed to win and keep the Navy Midshipmen at least two places behind them. At the start of the race, the Cougars made a tactical positioning play, pushing the Navy over the starting line early for a penalty. This forced the Midshipmen to circle around the committee boat before getting back into the race, giving the Cougars the significant lead they needed to take first on the leaderboard.
In sailing, if a boat crosses the starting line early, it must immediately circle back around the committee boat to restart properly; failing to do so results in disqualification from that race, and with the larger-size boats, the Navy lost 30 to 40 seconds off the start, enough for Charleston to seize a clear lead.
“It was more pertinent for us to stay in touch with the Navy boat and make sure they were at a minimum two spots behind us,” Wolff said. “We put ourselves in a position that made them go over early, putting them in a very unfavorable spot.
“We maintained our lead in first; once we were out in front, we had a very conservative race managing the fleet behind us, and we got a bullet,” said Wolff. (A “bullet” is an unpredictable surge in wind that can be utilized by experienced sailors to increase speed.)
As a lifelong sailor and captain of the team, Wolff said the most important aspect of being a successful team is maintaining extreme ownership and accountability to one another, and in this case to the Charleston sailing program.
“The biggest thing we work on as a team is being accountable to each other every day in everything we do,” said Wolff. “It’s not just showing up to the event and doing all the right things there –– it’s being in the gym throughout the week, watching film, and being there for your teammates, on and off the water.”
For Wolff, one of the main takeaways from his long sailing career is the friends he made along the way. After college, his goal is to continue sailing as much as possible.
“I am looking forward to sailing with friends and attending events in the future with teammates I’ve made here at College of Charleston,” said Wolff. “It’s just great to have made some of my best friends through sailing; at the Naval Academy event, I sailed against kids I have been sailing with since I was 5 years old.”
The College of Charleston’s next scheduled race is the ICSA Match Race Nationals in Florida from Nov. 15 to 17, against 10 of the country’s top sailing teams.
woot woot..Go Miles!! so proud of you.
Congratulations Miles!
To the author: a bullet in racing is a score of 1, when you come in first place your score is recorded as 1 point which looks like a bullet. The explanation you gave is inaccurate.
We are summer residents on MV and have watched Miles grow up – always sailing! What an incredible accomplishment for this young man! Way to go, Miles!
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