• 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

Because, after all, that is why we are named Courageous Sailing...
Youth Program
By Alessia Hughes, Instructor in Training The definition of a good sailor and a bad sailor are quite clear to practically anyone. A good sailor can sail fast even if the wind is not strong. A bad sailor gets stuck trying to maneuver in heavy winds. A good sailor is strong, bold, and able to succeed...
Continue Reading...
Conquering our fears together
Youth Program
By Kayla McLaughlin, SwimSailScience and Summer Learning Project Head Sailing Instructor   “Teachers of young children do one of the best things that there is to do in life: bring joy and beauty, mystery and mischievous delight into the hearts of little people in their years of greatest curio...
Continue Reading...
Don’t eat the creatures!
Green
By Emily Hart This week we had our first group of Step 1 students in the sailing school. As the youngest learners, we hope to keep them coming back for years and it’s important to get them excited about Boston Harbor! We had a great discussion about the animals they see in the harbor and played a W...
Continue Reading...
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...
Continue Reading...
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...
Continue Reading...

Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129

 

 

Thank you to our donors

Distrigas Logo BNY Mellon State Street Logo
alphagraphics Triumph Modular Building americorps Parks and Rec premier capers catering peterson party center gordons wine and liquor Catering Name Tag