For some of us, it’s all about the big boats, backup engines, and thoughts of sailing around the world. Our cruising fleet won’t take you quite that far, but it will take you around the harbor and then some. Whether you want to invite friends and family for trips around the Harbor Islands, anchor for a picnic lunch, spend a night moored or at anchor under the stars, or practice your big boat skills in preparation for a bareboat trip in the Caribbean, we’ve got a convenient cruising membership option for you. The Courageous cruising fleet is growing and improving every year, with boats ranging from 24 to 30 feet, including three J/24s, an O’Day 240, a Tartan 27, an Erikson 28, and a Seafarer 30. We offer three classes of cruising memberships: our entry level option (Cruising C) provides access to the J24s and O’Day 25 for day trips, the next level up (Cruising B) enables overnights for the same fleet, and our Cruising A option provides access to the full fleet for day trips and overnights. Cruising membership also includes access to our fleet of twenty five Rhodes 19s and nine J/22s.

We carefully limit our available cruising memberships to ensure everyone has plenty of access, so sign up soon! Starting Monday, December 2, we will make six 2014 memberships available at each of the three Cruising membership levels--if you are sure you want in, please email or call us ASAP and we will put you on the waitlist. If you’re interested in a cruising membership, please email Jake Denney, our Adult Program Director, at

Contact the Adult Program


Jake Denney

Adult Program Director
617-242-3821 x14