• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond
  • Work at Courageous

    The 2015 season is just around the corner, which means there is an opportunity for you to come spend your summer working at Courageous. You'll be outside and on the water with a great staff and sailors from age 8 and up. This could be the start of your lifelong passion for teaching sailing, educating, and organizing in your community. Read More
  • Leadership + Growth

    Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Read More
  • Environmentalism at Courageous

    Courageous is wind powered, but we do more than just use natural energy sources. For the past several years, our young sailors have been learning about marine biology and ocean cleanup from our own Environmental Educators and award-winning partners. Read More
  • Support Courageous Kids

    As 2014 draws to a close, Courageous is celebrating a successful year of teaching sailing and more to Boston kids, and looking ahead to next year. Please consider supporting Courageous in our mission to provide high-quality summer learning opportunities for the kids who need them most by making a tax-deductible donation to our Annual Appeal before December 31. Read More
  • Awareness Campaign

    See our new awareness campaign made by Hill Holliday and Courageous board member, Joe Berkeley. The campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids. Read More

Challenge15th Annual

Courageous Challenge Charity Regatta


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

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

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

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.

Frostbiting Week 10: Winter Series Ends, Frostbiting Rolls On with Valentine's Day Regatta
Thanks to everyone coming out this past Saturday, and helping us get 23 boats on the line in some very chilly conditions! Throughout the day, we had steady wind around 8-10 knots. Current was sweeping across the course, going out of the harbor, and seeming to slack through the afternoon. In the firs...
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Frostbiting Week 4: There is always a lot to learn.
First is when the tide is coming into Boston Harbor, the current is often going out. That was true all day on Saturday. There had been enough rain earlier in the week that they were dumping the Charles River. As Jim Watson, my very observant crew points out, fresh water is lighter than salt and th...
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Week 3 Recap: Overtaking at the Windward Mark
 I hope you are all staying warm and dry today. It is one of those days that you don't have to walk far before you look like you've fallen off the dock or been swept overboard. The good news is that this weekend should be warm (high of 45) and dry, with NW winds around 10 knots. I am taking a...
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Frostbing Week Two- Starts Are Hard
Barge- Move forcefully or roughly. Push, Shove, Force. "We can't just barge into a private garden party." or "Barging in at the start line causes havoc and makes Courageous staff anxious and competitors angry." Yes, this week's recap is about starts, and in particular, barging. Which there was a ...
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Week 1 Brings Great Weather, Great Racing
Current was coming straight down the course all day, making starts difficult at first. As the current slacked, the fleet was still pushing hard and we had several boats OCS, but no general recals occured.  In Race 1, the boats starting pin got over into a nice lefty shift, and were able to t...
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