Sailboat Availability
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.
2025 Boating Prices
| Regular | Boston Resident | |
|---|---|---|
| Hourly Rentals | ||
| Single kayak hourly | $25 | $20 |
| Double kayak hourly | $40 | $35 |
| Rowboat hourly | $40 | $35 |
| Sailboat hourly | $60 | $50 |
| Standup paddleboard (SUP) hourly | $25 | $20 |
| SUP Yoga hourly | $45 | $40 |
| Passes | ||
| Paddling Season Pass (rowboat, kayak, SUP) | $225 | $200 |
| Sailing Pass (includes Paddling Pass) (requires a checkout) | $400 | $350 |
| Sailing Checkout | $45 | $45 |
| Lessons | ||
| 2 Hour Sailing Lesson (1-on-1) | $120 | $90 |
| Learn to Sail Course (3-on-1) | $325 | $325 |
Hours
Monday: Closed
Tuesday: 3–Sunset Wednesday-Friday: 12–Sunset
Saturday & Sunday: 10 AM–Sunset
Contact Info
Sailing Address:
507 Jamaica Way
Jamaica Plain, MA 02130
Contact:
(857) 452-1770 (in season)
jamaicapond@courageoussailing.org
