Oakcliff Sailing Programs

Oakcliff Sailing Programs includes Acorn Programs for sailors 15 and older, with two-week summer intensives and shorter sessions focused on high-performance dinghy sailing, offshore racing, match racing, and Maxi yacht racing. It also includes the Sapling Program, a summer-long apprenticeship-type program for adults 18 years or older, plus weekend clinics and regattas. The program schedule includes sailing, boat work, and physical training.

Programs

• Acorn Programs — Sailors 15 and older · Two-week summer intensives; shorter sessions · Short-term programs focused on specific areas of the sailing industry, including high-performance dinghy sailing, offshore racing, match racing, and Maxi yacht racing.
• Sapling Program — Adults 18 years or older; also described as for those who want to become leaders in the marine industry or sailing professionals · Summer-long program; several months, and in some cases several years · Apprenticeship-type program for those who want to become leaders in the marine industry or sailing professionals.
• Weekend clinics and regattas — Weekend

At a glance

• Ages: 15–18 years old
• General schedule: A mix of sailing, boat work, and physical training.

About the provider

Oakcliff Sailing Programs was founded in 2010. Its leadership team includes Executive Director Dawn Riley and founding board member Dave Perry. The program states that its mission is to "Build American Leaders Through Sailing." It is an official training center of the US Sailing Team, 11th Hour Racing, NYYC American Magic, IYRS, and the World Match Racing Tour, has hosted more match racing events than anywhere else in the country, organized and hosted 19 regattas, and graduated over 300 sailors. It also offers scholarships and tuition assistance, and awards scholarships to graduates of community sailing programs.

Oakcliff accepts trainees with a wide variety of skill levels. Trainees who are self-driven, organized, and motivated thrive in Oakcliff’s flexible training environment. Those under 18 will be supervised by Residential Assistants during evenings and by Oakcliff faculty and the RAs during the day. They will share single-gender bunk rooms with not more than eight athletes per room.

What families say

“The perseverance in the face of adversity that I learned at Oakcliff has been a huge benefit in my life. I wouldn’t have felt comfortable putting so much on my plate had I not gone through the challenges I faced at Oakcliff.” — Matthew Hersey, 2018 Acorn Graduate, Student at Northeastern University

“Oakcliff taught me a ton - It propelled my sailing to a whole other level. I was able to start offshore sailing, which is something I love and adore. Oakcliff taught me inner strength, and how to “just get stuff done,” which is something wildly valued in my line of work.” — Ivy Binns, Acorn & Sapling Program Graduate, Senior Executive Assistant for VC

“Oakcliff definitely helped me earn my job at New England Boatworks. I gained a ton of experience in race prep and boatwork during my time as a Summer Sapling.” — Alexander Brock Kraebel, 2012 Sapling Graduate, Naval Architect at New England Boatworks

Last updated September 6, 2026.