• Fall is the perfect time to experience Boston Harbor, and Courageous Sailing is offering special deals for Charlestown residents. Summer vacation doesn’t need to be over.
  • Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Summer Youth Sailing Program
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families


Monday, Oct. 24th 2:30pm: Due to gusts up to 24 knots, no Red of Yellow Flag Skippers can sail until further notice. Please check back for updates.
  • Work for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    Registration is now closed. View the FAQ to learn what to do if your child was registered successfully or put on the waiting list. The FAQ also details the 2016 fees and scholarships. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More

2011 Summer Youth Program Registration

The 2011 Summer Youth Program application period closed on 3/21/2011. Registration/Waitlist confirmation letters were mailed on 4/19/2011.*

Important Dates for Registered Students:
  • Blue Enrollment Form Due: May 9, 2011
  • Payments Due: May 9, 2011
  • Last day for Cancellation & Refund: June 15, 2011
  • Last day to Submit Proof of Swimming: June 15, 2011

*Please Note: Confirmation letters regarding registration and waitlist status were mailed on April 19, 2011. Please allow one week from that date (until April 26) for delivery prior to calling the office if you suspect that your confirmation did not reach you. Thank You!

Instructions for Registered Students



Welcome to the
Courageous Sailing Summer Youth Program!

To confirm your attendance:

(1) Enrollment Form - Due May 9

Even if you are in Sailing 101, please return "Summer Youth Program Enrollment Form" (the blue piece of paper in your enrollment confirmation letter) to Courageous by Monday, May 9, 2011.

On the enrollment form, be sure to indicate whether or not you would like your child to attend the free Extended Day Program, and sign the Memorandum of Understanding.

Download an Extra Copy of the"2011 Summer Youth Program Enrollment Form"

(2) Apply for a Scholarship - Due May 9

The Scholarship Application may be found under Section 5 of the Enrollment Form, which is due by May 9, 2011.

Remember: If your child has been registered for Sailing 101, there is no need to apply for a scholarship.

(3) Make your Tuition Payment - Due May 9

Download the Enrollment Form for further instructions.


Click here to make an online credit card payment via PayPal.

See the Frequently Asked Questions page for more explanation of the payment process.

Remember: If your child has been registered for Sailing 101, there is no need to make a payment/deposit.

Note that no refunds on course fees will be granted after June 15, 2011.

(4) Submit Proof of Swimming - Due June 15

Courageous Sailing requires that all youth program sailors be able to swim 75 feet and tread water for 90 seconds.

As proof of your child's swimming ability,a photocopy of one of the items listed below must be submitted to us by June 15:

* YMCA Certificate of Completion for Polywog Level or above
* Red Cross Certification of Completion for Level V or above
* Boy/Girl Scouts Swimming or Lifesaving Merit Badge

* Letter stating swimming ability signed by lifeguard on pool letterhead

*This form (click to download) completed by a lifeguard after watching your child swim.


If you have any questions you can: (1) check out our FAQ page or (2) call or email Kate Henderson, the Youth Programs Director at 617-242-3821 x12.

Learning the Ropes
Youth Program
I had a great summer at Courageous Sailing and have had a number of memorable experiences with kids on the water. One that stands out most to me happened with a student in Step 2. This student was always his own person and has a very colorful disposition but, because of this, had trouble showin...
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Mi Barco es Su Barco
Youth Program
The Swim Sail Science! program at Courageous this summer was very different than the summer youth programs that we have always had. Half of the students' summers were spent in math and reading classes, where they learned about different water systems and our limited supply of fresh water i...
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Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
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Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
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More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129



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