• 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
  • 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

Challenge15th Annual

Courageous Challenge Charity Regatta

CLICK HERE FOR THE '09 FLYER
& REGISTRATION FORM!

May 18, June 1, 8, 15, and 22
6 pm to sunset

For the past thirteen years, the Courageous Challenge has been our most popular and successful corporate fundraiser.

What is the Courageous Challenge?

The Courageous Challenge is a corporate regatta and teambuilding event. By participating, your company is supporting Courageous' free programs for Boston youth, where over 10,000 children have learned to sail over the past eighteen years. Learn more about our youth programs!

How does the Challenge work?

The Challenge Regatta runs for four consecutive Monday nights (June 1, 8, 15, and 22 ), with a prepartory night of sailing and instruction on May 18.

The first night of the regatta is a "Racing Clinic". The evening includes practice races from 6pm to sunset. We will have coaches on hand to work with you on and off the water, all followed by fun awards and video coverage immediately following the races.

The next four nights are when the competition heats up! Each team races with their respective crews, and Gourmet Caterers provides a light buffet on the Courageous pier at sunset.
On the final night one young sailor from the Courageous Advanced Racing Program will join your team. The Challenge culminates with an awards ceremony and farewell barbecue.

No sailing experience is necessary to compete in the Courageous Challenge. If you request, our experienced and knowledgeable instructor staff will be on hand to show you everything you need to know. Also, keep in mind that the two to three people in your sailboat can change from week to week, this allows for more people to take part in the fun. But many teams have the same people racing each week.

Donation Structure

All Club levels include the application of the campany's name on one of our Rhodes 19s for the entire season.

Skipper’s Club $2,500
Benefits:

5 nights of racing on Boston Harbor.
Donation pays for:

15 children to attend the Courageous Learn to Sail Program.

Commodore’s Club $3,500
Benefits:

5 nights of racing on Boston Harbor.
Company logo in full color on the jib sail.
10 tickets to Courageous Sailing’s Make-A-Mark Gala.
Donation pays for:

15 children to attend the Courageous Learn to Sail Program and;
5 children to attend the Courageous Advanced Racing or Cruising Program.

Admiral’s Club $4,500
Benefits:

5 nights of racing on Boston Harbor.
Company logo in full color on the jib sail.
10 tickets to Courageous Sailing’s Make-A-Mark Gala.
Donation pays for:

15 children to attend the Courageous Learn to Sail Program;
5 children to attend the Courageous Advanced Racing or Cruising Program, and;
One teenage sailor to attend our Instructor In Training Program.

If you would like to register or if you have questions about the Challenge Regatta, please contact our Executive Director, John Maconga at john@courageoussailing.org, (617) COURAGE ext. 16.

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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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129

 

 

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2016-MAM-Mainsail-Sponsors

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