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Sailing

Several sailboats with numbered sails race on choppy water under a cloudy sky, with a distant shoreline visible.

 

Harnessing the Wind: A Legacy of Competitive Excellence

For decades, the Milton Academy Sailing program has been a formidable presence on the waters of New England, defined by a pursuit of tactical mastery and a commitment to the art of the start. As a prominent member of the New England Schools Sailing Association (NESSA), the Varsity team is a consistent contender on the national stage, regularly vying for New England Championships and competing in elite-level events across the country. Our history is one of steady progression and high-stakes performance, yet our future is anchored in the continuous evolution of our sailors’ technical prowess.

Operating out of our dedicated facilities at Marina Bay, the Varsity squad utilizes a fleet of twelve Club 420s to sharpen the split-second decision-making required for elite team racing. At Milton, we view the boat not just as a vessel, but as a laboratory for physics, strategy, and resilience. Our sailors graduate to some of the most prestigious collegiate sailing programs in the nation, carrying with them the "Milton edge"—a sophisticated understanding of wind patterns, boat speed, and the mental fortitude necessary to navigate the most challenging conditions.

Two people in a sailboat with a white hull and sails are in the foreground, while a calm, green body of water stretches into the background.
Two young sailors navigate a white sailboat with a blue and orange horse logo on its sail across a calm body of water under a bright, cloudy sky.
Two young sailors in blue and orange vests grip ropes on a sailboat, with a blurred blue background of water and sky.

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Schedule & Results

1st Team

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The Fleet

Milton Academy Sailing trains and competes aboard a fleet of twelve Club 420s — the gold standard of high school competitive sailing. The Club 420 is a two-person centerboard dinghy designed specifically for the development of young sailors, offering the perfect balance of performance and accessibility. Responsive enough to reward technical skill and tactical awareness, the 420 is the vessel on which some of the country's best collegiate and professional sailors first found their footing.

With twelve boats and four days of practice per week on Marina Bay, every Mustang sailor gets meaningful time on the water — building the boat-handling skills, crew communication, and racing instincts that define competitive sailing at the highest level.

A young sailor navigates a small sailboat with a distinctive logo and number on its sail across choppy water, with a hazy industrial structure visible in the distance under a cloudy sky.

The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails.

 

Program Philosophy: Precision, Partnership, and Play

"The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails." At Milton, we believe that sailing is the ultimate teacher of adaptability and collective trust. Our philosophy is rooted in the unique demands of Team Racing, where three boats must move as a single, cohesive unit to outmaneuver the opposition. In this arena, your teammate’s success is inextricably linked to your own; we don’t just race alongside one another—we race for one another.

Our culture is intentionally vibrant. We find the rhythm in the rigging and the fun in the spray. We embrace the intellectual intensity of a perfectly executed "mark trap" while maintaining the lighthearted spirit that makes life on the water so transformative. From the spirited debates over tactical theory on the team bus to the laughter shared at the docks after an afternoon of practice, our traditions are the heartbeat of the program. We foster an environment where every sailor is encouraged to lead with empathy and where the friendships forged in the cockpit become the foundation for a lifetime of connection.

Several small sailboats with colorful sails race across choppy water under a cloudy sky, with a distant shoreline visible.

A Place for Every Sailor

Teams: 1st Team, 2nd Team

The Milton Sailing program is structured to offer a sophisticated and rewarding experience for every student, regardless of their prior experience on the water. We believe that the ocean is the great equalizer, and we provide the infrastructure for every student to find their sea legs.

Whether you are an All-American prospect or a beginner discovering the pull of the mainsheet for the first time, our mission remains the same: to use the water as a venue for personal growth and student leadership. Our JV program emphasizes the foundational mechanics of boat handling and the nuances of sportsmanship, ensuring that those who sail for fun and connection receive the same high-level coaching and athletic support as our elite competitors. At Milton, there is a space for every athlete to shine—whether you are the tactician calling the shifts, the crew executing a flawless gybe, or the teammate whose energy lifts the entire fleet. We play with pride, sail with joy, and always look toward the horizon with confidence.

Two young sailors lean into their boat as it cuts through the water, with a tree-lined shore visible in the background under a clear blue sky.
A young man in a blue life vest with an %22M%22 on it gestures towards sailboats docked in a harbor with buildings in the distance.
A young sailor in a small boat with a purple and white sail maneuvers the ropes in choppy water, with a hazy cityscape visible in the distance.

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Coaching Staff

Patrick Broome

Head Coach

Coach Broome brings competitive sailing experience and a deep commitment to student development to the Milton Academy program. A former collegiate sailor at Hobart and William Smith College — one of the most decorated sailing programs in the country, home to over 70 All-Americans — he brings a firsthand understanding of elite fleet and team racing to every practice on Marina Bay. 

An administrator in the Lower School, Coach Broome's background in school leadership informs his approach on the water, where sportsmanship and character development are as important as tactical execution. He also serves as a coach for the Milton Ski program, bringing a multi-sport perspective and year-round presence to his work with Milton student-athletes.

Three people in life vests stand on a dock with boats and buildings in the background.

Caroline Sacchetti

Assistant Coach

Coach Sacchetti brings a collaborative, student-centered approach to the Milton Academy sailing program and a lifelong passion for competitive sailing on the water. Her deep familiarity with the tidal and wind conditions of the New England circuit allows her to provide Mustang sailors with the nuanced, real-time feedback needed to master boat handling and wind strategy during high-stakes NESSA competition.

Beyond the physical mechanics of the sport, Coach Sacchetti is a dedicated mentor in the strategic and mental dimensions of team racing — working closely with sailors to develop the split-second communication and tactical awareness required for elite Club 420 performance.

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Two young sailors in the foreground navigate their white sailboats with orange and blue accents, while other sailboats with red and green sails are visible in the blurred background on a cloudy day.

Honors & Awards

Milton Academy Sailing has a history of competing — and winning — at the highest levels of scholastic sailing, from NESSA competition on Marina Bay to national and international championships. The program's record reflects a sustained commitment to excellence that spans decades and reaches well beyond New England.

In 2002, the Mustangs claimed the Interscholastic Sailing Association National High School Team Racing Championship — the Toby Baker Trophy — defeating a field of twelve teams from across the country. That summer, the same core group traveled to England and won the British Schools Dinghy Racing Association (BSDRA) Team Racing Championship, defeating thirteen British teams to claim a world title. In 2015, five Milton sailors competed in the International Sailing Federation's Team Racing World Championships in Rutland, England, winning gold in their division and claiming the final gold honors in youth racing. Milton also claimed the Baker Trophy national qualifier in 2015, and most recently finished third in the nation at the 2026 National Team Race Championship.

Program Milestones

 

2026 National Team Race Championship — 3rd Place

2015 Baker Trophy National Qualifier — Champions

2015 ISAF Team Racing World Championships — Gold Medal (Youth Division)

2007 National High School Sailing Championship (Fleet Racing) — 6th Place; 1st in New England

2002 BSDRA Team Racing Championship (England) — World Champions

2002 Toby Baker Trophy — National Team Racing Champions

Christina Sakellaris '17 — NESSA Singlehanded Championship (Nancy Healy Trophy), Radial division 

Dylan Cafferty '27 — NESSA Singlehanded Championship (Nancy Healy Trophy), ILCA 7 Open division

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Season Highlights

Two smiling young people in life vests give hand gestures from a sailboat, with other sailboats and a blurred shoreline in the background.
Two young men in life vests lean out of a sailboat with the number 17 on its side, as houses and trees line the distant shore under a bright sky.

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Mustangs at the Helm

The Milton Academy Sailing program is a premier training ground for athletes who possess the tactical intelligence, technical skill, and composure required to compete at the highest levels of collegiate sailing. Our alumni carry the Milton legacy of "precision and partnership" to the most competitive waters in the country, competing in the Inter-Collegiate Sailing Association (ICSA) and beyond.

College Pipeline:

 

Liam Boukris ‘24, Connecticut College

Will Bourell '23,  Harvard University 

 

 

Ryan McGauley ‘23, Boston College

Emma Wang ‘23, Massachusetts Institute of Technology

 

Cate Anderson ‘22, Tulane University

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