• 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
  • Support Courageous Kids

    As 2015 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
  • 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
  • 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

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

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...
Continue Reading...
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...
Continue Reading...
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...
Continue Reading...
How Blue Note came to Courageous
One of of my favorite stories of 2015 is the arrival of Blue Note.   A comfortable yet sprightly 30 footer in wonderful condition, Blue Note comes to us through the generosity of the family of Dr. Paul Blum, a remarkable scientist, Peace Corps volunteer, and Boston Harbor sailor.  Blue Not...
Continue Reading...
Happy, Excited, and Free
Youth Program
For the past four years, I have had the privilege of working with students from Swim Sail Science, a program Courageous created in partnership with Boston Public Schools. The SSS program aims to serve students who are at risk of summer learning loss. These students continue their academic studies th...
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