• Lottery Registration Opens: February 1, 2025
• Lottery Registration Closes: February 15, 2025
• Confirmation Letters emailed: March 1, 2025

• 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 receive confirmation of their status, whether registered or wait-listed, via email once the lottery is run.

At Courageous we are committed to making sailing accessible to all, regardless of income.

Full Scholarships ($0 class fees) are available to families on government assistance and low-income households. For the city of Boston in 2022, "low-income" is defined by HUD’s Office of Policy Development and Research as less than $110,000 per year.

Partial Scholarships (~50% discount) are available to households whose income is at or above $110,000 but below Boston's median-income level of $150,000.

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 ypfrontdesk@courageoussailing.org with any questions. 

If your income or financial situation puts you in a fee bracket that you can’t afford, please contact us at ypfrontdesk@courageoussailing.org and we will work with you so that your children will be able to attend.

Class fees for the 2025 season:

The amount of fees owed are sent to you with your registration confirmation. This amount reflects anticipated scholarships. You can pay this invoice online with a credit card via a personalized link included in your registration packet. To receive the link again, contact ypfrontdesk@courageoussailing.org. You can also pay by submitting a check (payable to “Courageous Sailing”) or by dropping off cash at Courageous Sailing. Payment in full is due by March 30th, or if your child was accepted off the waitlist, within 7 days of the acceptance.


A note on class fee increases in 2025: 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 significant increase in available program spots. 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. We also strive to compensate our incredible staff fairly while taking inflation into account. 


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 $700 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 is in no respect 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:

• Increasing class offerings program-wide
• Purchasing the dinghies we’ll need in the coming years to accommodate the growing number of advanced sailors
• Maintaining our current fleet and replacing aging boats
• Paying our instructors industry competitive rates