Private Keelboat Charters

A private charter is a fun opportunity for a group of up to 3-5 people to get out on Boston Harbor in a sailboat, with no need to worry about planning a thing! Experience the fantastic views of the city from the water, learn some sailing skills or take the helm if you’d like, check out some Boston landmarks, or just sit back and enjoy the ride.  An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise for you.  We have a variety of boats available for charter, including Rhodes 19s (comfortable 19-foot keelboats that fit up to 3-4 people), J/22s (faster, more responsive keelboats that fit up to 4 people), and our cruising boats, which can fit 4-5 and are suitable for longer trips around the Harbor Islands.  Feel free to bring a picnic or snacks for the sail (note that alcohol isn’t permitted before or during sailing).  Life jackets are provided.  Minimum of 2 hours; price includes as many guests as can safely fit on the vessel. 

Courageous can also accomodate private groups requiring 2 or more boats. See our Corporate Functions page for more information. 

Rhodes 19: $95/ hr (Minimum of 2 hours per lesson; price includes up to 4 guests.)
J/22: $125/ hr (Minimum of 2 hours per lesson; price includes up to 5 guests.)
Cruising Boat: $150/ hr (Minimum of 2 hours per lesson; price includes up to 6 guests depending on vessel.)
Please contact us directly at 617.242.3821 to set up your private charter. 

Contact the Adult Program


Bryan Lee

Adult Program Director
617-242-3821 x14

Courageous’s sailing season runs from May 1 to October 31. Basic Keelboat Complete course must be taken over two consecutive weekends, Saturday and Sunday from 10-4:30 each day, and completed before October 31. At the conclusion of your course, you’ll need to demonstrate competency and knowledge of sailing basics in order to sail as a member. Courageous membership includes fleet access, plus free or discounted member activities like cookouts, camping trips, moonlight sails, racing, and more.