Group Teambuilding

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

Getting Started

Never been sailing? Get ready for the ultimate adventure! In just one lesson you'll be out on the water. If you like it—which we're sure you will—before long you'll be skippering a boat, racing on a team, or cruising around the harbor islands. If you stick with it, one day you could even be a Courageous instructor!  While you're on the water, you're going to learn lots about the environment and get to practice some pretty important life skills, too. From fishing off our pier to overnight island camping trips, you'll be having fun on adventure after adventure, all year long!

Read the website and still have questions? Email your questions to Ashton Smith at ashton@courageoussailing.org or call 617-242-3821.



Courageous Mainsail Partners


alphagraphics Triumph Modular Building americorps Parks and Rec premier capers catering peterson party center gordons wine and liquor Catering Name Tag