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

  • 2-Hour Private Lesson or Harbor Cruise just $95!

    If you know someone who would love to give sailing a try (or take their skills up a notch with a private lesson), this is the perfect gift! This two-hour sail is an opportunity for up to 3 or 4 people to experience the fantastic views from Boston Harbor, learn some sailing skills at any level, or just sit back and enjoy the ride on a comfortable, stable Rhodes 19 keelboat. An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise. Read More
  • 20% off our introductory Basic Keelboat Complete course

    In just 2 weekends, our Basic Keelboat Complete course will give a total sailing novice the opportunity to learn all they need to sail on their own, for just $440. This hands-on 24-hour US Sailing course is taught by one of our expert instructors in a 19 foot keelboat with up to 3 students. Combine the course with a Full or Family membership (25% off!) so that the newly minted skipper will be able to sail at Courageous all season long. Read More
  • 25% off Full Individual and Family Memberships

    A Courageous membership means that you can take one of our boats out for a sail on Boston Harbor whenever you’d like. Mem- bership also includes much more: barbeques, racing, fireworks- watching parties, moonlight sails, Harbor Island camping trips, and discounts on courses. You’ll be a part of an enthusiastic, inclusive community of sailors...and you’ll be helping Courageous provide free and low-cost sailing opportunities for Boston kids. Read More
  • 15-20% Off All Other Courses and Memberships

    Know somebody who’s ready to take their sailing skills up a notch, or who is looking for a way to get out on the water without the hassle and expense of boat ownership? Courageous has a variety of courses, ranging from a 12-hour beginner course to Advanced Keelboat to Bareboat Cruising, to challenge sailors of any level. Our different memberships offer access to the boats in our fleet, so that old salts and graduates of our courses can sail Boston Harbor in style. Read More
   
 

Sail With Us

 
 

Become a member

Learn about courses

 
 

Contact the Adult Program

 

Jake Denney

Adult Program Director
adultprogram@courageoussailing.org
617-242-3821 x14

DISCLAIMER: Courageous’s sailing season runs from May 1 to October 31. Basic Keelboat Complete course must be taken over two consecutive weekends, Saturday and Sunday from 10-4:30 each day, and completed before October 31. At the conclusion of your course, you’ll need to demonstrate competency and knowledge of sailing basics in order to sail as a member. Courageous membership includes access to our fleet of 25 Rhodes 19 keelboats, plus free or discounted member activities like cookouts, camping trips, moonlight sails, racing, and more.