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 on our 17ft Cape Cod Daysailors, rowboats and kayaks rentals are also available. For news and updates, follow Jamaica Pond on Facebook.

Hours of Operation

May 15th-October 31st

Mon-Tues- 2:00 pm – 6:30 pm
Wed- Closed
Thurs-Fri- 12:00 pm – 6:30 pm
Sat-Sun- 10:00 am – 6:30 pm
Holidays- 10:00 am – 6:30 pm

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


Rowboats rentals: 2022 rates pending
Kayak and sailboat rentals: 2022 rates pending
Private sailing lessons or cruises: 2022 rates pending

Lessons must be scheduled at least one week in advance by calling the boathouse.

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.

Learn More

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.

Contact Info

Sailing Address:
507 Jamaica Way
Jamaica Plain, MA 02130

(857) 452-1770 (in season)
617.242.3821 (off season)