JP1: Sailing 101

Jamaica Pond One (JP1), formerly Step 1, is our one-week beginner sailing course offered to children ages 8 and up from the City of Boston.



In Step 1, your sailor will get their first taste of sailing at Courageous. They will explore Jamaica Pond, learn the parts of a sailboat and their purpose, and start practicing basic skills that will be important in their future on the water, like rigging/derigging, skippering, and tying knots. Though students will leave the pier with a lot of new knowledge and stories, our main goal is to get every sailor more comfortable and confident while out on the water and excited to keep sailing. To reach this goal in the 1-week (4 or 5 day) session, our instructors will teach through a fun, high-energy, game-based approach aboard Cape Cod Daysailers and RS Ventures. Days may include a scavenger hunt, a raucous round of Follow the Leader, and plenty of fun, games, and crafts during on-land time. No prior sailing experience is necessary, though all students must be able to demonstrate a minimum level of swimming competency.

If a student has never sailed before or is new to Courageous and you want to sail at Jamaica Pond, JP1 is the class for them.

Sample Daily Schedule:

8:45 Arrival
8:45-9:00 Games and Activities in the tent with instructors
9:00-9:30 Chalk Talk – go over the water skill or activity of the morning
9:30-10:00 Rigging the boats
10:00 – 12:00 Sailing
12:00-1:00 Lunch and activities in the tent
1:00-3:00 Sailing
3:00-3:30 Derigging
3:30 Dismissal

Course Information

Dates Duration Tuition
July 5 – July 15 (no program on July 4) 9 days* $975
July 19 – July 29 (no program on July 18) 9 days* $975
August 1 – August 12 10 days* $975
Jamaica Pond
Daily schedule:
8:45am – 3:30pm
Extended day:
8am – 5pm (*Requires additional $50 tuition)

* Boston Parks and Recreation Department (BPRD) will be soliciting proposals for managing Jamaica Pond in the upcoming year. This is a standard and public process designed to promote transparency and quality contracting for the City of Boston residents. The BPRD has confirmed that a boating program will be operated at Jamaica Pond beginning in Spring 2021, but, while their application and review process is underway, our plans for programming at Jamaica Pond in 2021 and beyond will remain uncertain.

We are hoping to have a decision before our lottery registration opens on March 1st. Currently, we are planning to open our Summer Youth Program registration for our Jamaica Pond site – whether or not we have a final decision by that point. However, until we receive a decision, we will not be able to confirm course enrollments.

How fees are set
What to bring each day
Swim test requirement


Courageous Sailing YP Team
Admin Staff