Sailboat rentals require that you pass an on-the-water sailing checkout. Please call or email in advance to set up a checkout.
Make a Reservation
Online reservations are available for rowboats, kayaks, paddleboards, SUP yoga, and sailors who have been checked out. For member reservations, checkouts, and sailing lessons, please call or email us.
Youth Program at JP
At Courageous Sailing, youth experience sailing as a platform to develop leadership skills, gain confidence, and delve into hands-on science.
|1 Hour||2 Hours|
Boston Resident Discount: $5 off 1 hour rental, $10 off 2 hour rental
Season Passes and Classes
|Paddling season pass (rowboat, kayak, SUP)||$200|
|Sailing season pass (includes paddling)||$400|
|SUP yoga class||$45|
|2 hour sailing lesson||$90|
|12 hour Learn to Sail 1||$355|
Boston Resident Discount: $25 off paddle pass, $50 off sailing pass, $5 off SUP yoga, $10 off 2 hour sailing lesson, $35 off Learn to Sail 1, $5 off Checkout
507 Jamaica Way
Jamaica Plain, MA 02130
(857) 452-1770 (in season)