Sailing on Jamaica Pond

Courageous is pleased to offer youth and adult programming on Jamaica Pond in cooperation with the Boston Department of Parks & Recreation. In addition to sailing lessons and rentals, rowboats and kayaks rentals are also available. For news and updates, follow Jamaica Pond on Facebook.

Summer Youth Program at Jamaica Pond

At Courageous Sailing, youth experience sailing as a platform to develop leadership skills, gain confidence, and delve into hands-on science.

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Hours of Operation

Patriots Day Weekend – October 31st

Mon – Fri 12:00 PM – sunset
Sat – Sun 10:00 AM – sunset
Holidays 10:00 AM – sunset

Courageous at Jamaica Pond may suspend operations or close early due to a weather event. Check our Facebook Page for updates.

Boat Availability

The Summer Youth Program will run Monday – Friday, 9am to 3:45pm in July and August – sailboats are unavailable during this time. On weekends during the season, it’s best to call ahead.


Rowboat, kayak and sailboat rentals are $15 per hour ($10 per hour for rowboats with a fishing license).
Private sailing lessons or cruises are $45 per hour. Lessons must be scheduled at least one week in advance by calling the boathouse.

How to find us

Sailing Address:
507 Jamaica Way
Jamaica Plain, MA 02130

617.522.5061 (in season)
617.242.3821 ext. 12 (off season) (in season) (off season)