The Regatta for Entrepreneurship is an invitational sailing regatta on Boston Harbor, bringing together local growth companies and service providers to raise money to support the youth of Sealander Sailing Academy. Sealander provides coastal sail training and racing opportunities for youth 14 to 24 regardless of socioeconomic background, skill level, or physical ability.
Nexxus Group, Bowen Advisors, and Starboard Services. PHOTO BY BIANCA DROUIN
The regatta format recreates the match-racing of America’s Cup golden days, with two Sealander yachts racing to win the prestigious Founder’s Cup. Each yacht will have a core crew of 4, with 6 sponsor guests aboard. The sailing is guaranteed to be competitive. Team USA vs. Team UK. There is no second!
WHEN: Wednesday, July 22, 2026 (subject to change)
Noon to 3pm aboard Northern Lights (Boarding 11:30am)
The Regatta Spectator Floating Party is the networking event of the summer, as 150 entrepreneurs and service providers are celebrated for their contributions to the Boston ecosystem aboard the classic yacht Northern Lights.
SEALANDER SAILING ACADEMY 