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

    Courageous is wind powered, but we do more than just use natual energy sources. For the past several years, our youngsters have been learning about marine biology and ocean cleanup through award winning partner programs. Read More

Group Outings & Team Building Events

As a destination management and event planning company, we work with many supplier/partners, and experience a varied level of service. Your team is at the top of our list, because you make it easy for us to do our job from start to finish. We have received so many wonderful reviews from our clients that we send to you, and that means so much to us. - Kathleen Landry, President, Destination Partners

Sailing from our beautiful pier is a prize venue for an active group of any size.  Courageous offers a wide array of customized outings staffed by our professional instructors that are getting rave reviews. Designed to meet your specific needs, events at Courageous can include relays, regattas, or harbor cruises.

Common event types include:

The Fun Regatta: We start with a two-hour lesson so everyone can learn to sail and work together. The lesson is followed by a light refreshments and soda. After the break, go back out on the water for racing, and cap off the day with an awards presentation. Contact Dave for more information or to book a fun regatta.

The “College-style” Team Racing Event: This event is great for larger groups, as it allows several divisions to compete at alternating times. This format encourages camaraderie and team spirit. Each team has teammates on the water throughout the day, giving everyone a chance to win. Those on shore can cheer on the racers from the pier or just relax and enjoy refreshments dockside. Contact dave for more information or to book a team racing regatta.

The Leisurely Sail: This is the most casual type of outing. Participants can spend the day learning to sail, or tour points of interest in Boston Harbor. Contact Dave for more information or to book a leisurely sail.

…and our new offering, The BoatWorks Challenge, a day of experiential leadership development and team building geared towards business people faced with the challenge of building high performance, highly-motivated teams in today’s difficult climate, created and facilitated by our partner, Group Experiential Learning (GEL). The BoatWorks challenge is similar to an obstacle course, but individual boats can’t go it alone. Success requires extensive collaboration between sub-teams via hand-held radio. For more information check out our GEL page or call 1-888-GEL-TEAM to discuss your specific objectives with a GEL team member.

We recommend Gourmet Caterers for your food and beverage needs. Their professional staff is familiar with our facility and never fails to provide outstanding service.

Remember – all proceeds from your event fees fund Courageous’ Youth Programming Operations

Step 4: Cruising learning lessons!
Youth Program
Written by Step 4 Assistant Leader, Ian Hay Today I regained my faith in adolescents’ possession of common sense. The day was intolerably muggy and boat assignments seemed dubious as I watched my students tack deep close reach to deep close reach up out of the Mystic. We had already narrowly escape...
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Welcome back to Environmental Education at Courageous Sailing!
Green
By Emily Hart, 2014 Environmental Education Program Coordinator: I’m excited for my first summer at Courageous as the Environmental Education Program Coordinator. We’ve had a great first week! We have two initiatives this summer to encourage staff and students to take positive actions on environme...
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Day 4 of the Challenge
Challenge
By Judith Krimski Ladies in da House! This intrepid reporter, AKA Master of the Obvious has noticed that WOAH! THE LADIES are dominating Corporate Challenge 2014. We racing sailors are all cognizant of the fact that sailing is a male dominated sport. I am reminded of this every time I go to a Lase...
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June 16- Day 3 Recap
Challenge
Monday, June 16. By resident Challenge Blogger Judith Krimski.  Yes, there was more of that sailboat racing stuff on Boston Harbor. Winds veering from easterly sea breeze to SW. It never fails. Just another stellar night on Boston Harbor and my "happiness quotient" is a solid 9.99999. Every t...
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Corporate Challenge - Night 1 - June 2nd
Challenge
Wind: South 8-10 knots with some higher gusts. Windward/leeward course was set from North to South. W4s were the call of the night. Fleet consisted of nineteen Rhodes 19s. We get all sorts of people who enjoy sailing at Courageous: kids in summer programs, families, young adults studying at local...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129

 

 

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