Sign Up for the Summer Youth Program

Every year Courageous serves 1,000 youth from the Boston area. We are working hard to expand our capacity and have been able to provide substantially more hours of sailing per child in recent years. Still, we receive more applications than we are able to fulfill.


Steps To Lead

Registration is via a lottery to provide equal access to all families, regardless of their ability to pay.
The lottery will open for registration from March 1-15, 2018.

Swim Sail Science

Registration is limited to students identified as being eligible for the program from Harvard-Kent, the Eliot, Orchard Gardens, and Warren Prescott. For more information, please contact the Director of Youth Programs and Outreach.

2018 Youth Program Courses

Course Location Dates
Swim Sail Science Charlestown July 9 - Aug. 10
Step 1 Charlestown July 2 - 6
Step 1 Charlestown Aug. 14 - 17
Step 2 Charlestown July 2 - 20
Step 2 Charlestown July 24 - Aug 10
Step 3 Charlestown July 2 - 20
Step 3 Charlestown July 24 - Aug 10
Step 4 Charlestown July 2 - 20
Step 4 Charlestown July 24 - Aug 10
Step 5 Charlestown July 2 - July 20
Step 5 Charlestown July 24 - Aug 10
Step 6 (IIT) Charlestown June 25 - Aug 13
JP1: Beginner Jamaica Pond July 2 - 6
JP1: Beginner Jamaica Pond July 9 - 13
JP1: Beginner Jamaica Pond July 17 - 20
JP1: Beginner Jamaica Pond July 23 - 27
JP1: Beginner Jamaica Pond July 30 - Aug. 3
JP1: Beginner Jamaica Pond Aug. 6 - 10
JP2: Intermediate Jamaica Pond July 2 - 13
JP2: Intermediate Jamaica Pond July 17 - 27
JP2: Intermediate Jamaica Pond July 30 - Aug. 10
UMB1: Beginner UMass Boston Aug. 14 - 17
UMB1: Beginner UMass Boston Aug. 20 - 24
UMB2: Intermediate UMass Boston Aug. 14 - 24

Lottery Information

Registration is lottery-based and there is no advantage to submitting a registration form early. We have moved away from a first-come-first-served system in an effort to create a more equitable system. All lottery registration forms received will be processed in the following order of priority: (1) returning students, (2) siblings of returning students, and finally (3) new students who have no siblings in the program.

Important Dates

  • Lottery Registration Opens: March 1
  • Lottery Registration Closes: March 15
  • Confirmation Letters mailed/emailed by April 1

Rules and Restrictions

  • All Courageous Steps To Lead students must provide proof of their ability to swim 75 yards and tread water for 90 seconds. All students in Step 3 and above will be subjected to an onsite "swim check" by Courageous instructors.
  • Before registering for the lottery, please note the age and skill requirements for each Step. For returning students, please refer to the email sent out prior to registration with your child's recommended step.
  • All students entering the lottery for Jamaica Pond classes must be Boston residents per order of the Boston Parks and Recreation Department. Courageous Sailing reserves the right to require proof of address.
  • All students whose lottery registration forms have been processed will received confirmation of their status of registered or wait-listed.

Scholarship Information

Full scholarships

($0 class fees) are available to families on government assistance or with a household income of less than $70,000.

Partial scholarships

(~50% discount) are available to those with a household income between $70,000 and $140,000.

There is no separate scholarship application form - it is included in the lottery entry form. Please review the Summer Youth Sailing FAQ for additional information or email the Director of Youth Programs and Outreach with any questions.

Note: If your income puts you in a fee bracket that you can’t afford, we will work with you so that your children will be able to attend.

How Program Fees are Set

Courageous Sailing is committed to providing high-quality sailing programs to youth in the Boston area regardless of their ability to pay.

In the last few years, we’ve made major investments to grow our capacity - enabling a 21% increase in available program spots last summer alone. We’ve done this while improving program quality, keeping the majority of our classes three weeks in duration, and maintaining one of the lowest students to instructor ratios among Boston-area youth programs. The big investments we’re most excited about include:

  • 12 new RS Quest dinghies for Pier 4 and Jamaica Pond
  • Growing our Step 2 capacity by 36%
  • Growing our IIT program from 15 to 20 young instructors
  • Doubling our acceptance rate of new applicants
  • Introducing programming at UMass Boston in Dorchester

In order to help us continue to provide opportunities for all current students, and increase capacity to accept new students, over the next few years we will gradually increase class fees to better offset our real costs per student (currently $600 per week). We remain committed to providing sailing programs to youth regardless of ability to pay, which means:

  • Scholarships continue to be readily available for all who qualify.
  • We do not want this increase in class fees to be a barrier for any new or returning student. We are committed to working with every family to ensure that your children will be able to attend
  • The registration and lottery process for admittance to the Courageous Sailing Summer youth programs is “Need-Blind.” This means that admission, in no respect, is based on ability to pay

By helping us to cover the true costs of programming, we will be able to direct more of our fundraising efforts to the following capacity-building priorities:

  • Grow our capacity by increasing class offerings at UMB in Dorchester
  • Purchase the dinghies we’ll need in the coming years to accommodate the growing number of advanced sailors
  • Replace our aging fleet with new boats
  • Raise instructor wages to more competitive rates
  • Purchase a fleet of boats for UMB

Please don’t hesitate to contact the Director of Youth Programs and Outreach with any questions, concerns, or if the fee bracket you fall in is a barrier to participation.


2018 Youth Program Fees

Class Cost per week Class Fee Partial scholarship Full scholarship Admin fee
Step 1 (4-day) $325 $325 $160 $0 $10
Step 1 (5-day) $350 $350 $175 $0 $10
Step 2 $300 $900 $450 $0 $10
Step 3 $300 $900 $450 $0 $10
Step 4 $315 $950 $475 $0 $10
Step 5 $315 $950 $475 $0 $10
JP1 (4-day) $325 $325 $160 $0 $10
JP1 (5-day) $350 $350 $175 $0 $10
JP2 $315 $625 $315 $0 $10
Extended Day $40 $20 $10 --
  • Contact

    Ashton Smith
    Director of Youth Programs and Outreach
    (857) 452-1763