Boating on Jamaica Pond

Jamaica Pond Boathouse offers excellent sailing instruction and a new fleet of kayaks and standup paddleboards. Come experience this beautiful Boston Park from the water!

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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.

Make a Reservation

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

Hourly Rentals

	1 Hour	2 Hours
Standup paddleboard	$20	$35
Single kayak	$20	$35
Double kayak	$35	$55
Rowboat	$35	$55
Sailboat	$45	$70

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
Sailing Checkout	$45

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