Looking for the perfect way to build team spirit among staff members and network with some of Boston's premier companies? We've got you covered! Join us for some friendly competition in support of Courageous Sailing's Summer Youth Program!

Courageous Challenge Charity Regatta

The warm weather and late sunsets of May and June herald the Courageous Corporate Challenge. Over four Mondays, seasoned and novice racers alike set sail from the Charlestown Navy Yard, enjoying fast-paced, college-style, short-course keelboat racing in company-sponsored boats. Back on land, participants enjoy terrific food, drinks and camaraderie. 

The Challenge is more than just a good time--it also helps Courageous ensure that kids from all walks of life can experience the life-long learning opportunities and growth that sailing offers. Our programs have never been more vital, helping Boston kids recover from the stress and learning interruptions of the pandemic and allowing metro Boston residents of all ages to enjoy their harbor. We are committed to providing our community with high-caliber sailing and science programming--free for those in need--and we welcome your help! The generosity of our Challenge teams supports the Courageous mission and the kids we serve.

 2023 Schedule

  5/22     Race Night 1 
  6/5       Race Night 2 
  6/12     Race Night 3 
  6/26    Race Night 4 + Awards

Results, documents and contacts

Keep up with this year's results:

2023 Results

2022 Race Documents


Dave DiLorenzo  or

Caitlyn Ridgely

Join the Fun

Your company can decide to use your Corporate Boat as a weekly perk and rotate the crew for each night of sailing, or draft a dedicated team of employees for the entire Challenge and try to win it all. Either way, it's sure to be a memorable experience and a fulfilling way to spend a Monday evening supporting Courageous' mission.

With one boat, 2-4 Challenge team members can enjoy each evening of competition and fun; two boats accommodate 4-8 team members at a time, and three boats allow 6-12 to participate. Your company's logo will be proudly displayed on the jib sail of each boat for the year. Employees will be able to access the fleet, take advantage of discounts on lessons, and participate in member events all season long through the included corporate membership. And, last but definitely not least, you'll be providing a summer of fun and learning for Courageous kids!

Courageous Corporate Membership

Equivalent to a full-season, individual Rhodes 19 membership, but shareable by your whole company!*

  • included with company entry
  • treat your family, friends, & clients
  • enjoy member benefits
  • discounted sailing courses
  • continue racing on Tuesday and Thursday nights
*Limit one boat at a time
Your Impact

Thank you for helping Courageous deliver our mission: to transform lives through sailing programs that inspire learning, leadership, and personal growth.

At Courageous, kids from all backgrounds come together to learn, challenge themselves, and experience the joys of sailing. Your company’s participation in the Courageous Challenge helps ensure equitable access to our youth programs, along with free meals, school bus transportation, ongoing swimming lessons, and access to on-staff social workers for students in need. Over half of our sailors participate for free, and even more receive partial scholarships. Swim Sail Science, our free Boston Public Schools summer learning program, serves 60-90 economically disenfranchised students each year, many of whom would not otherwise have had access to their harbor or the sport of sailing. Extensive evaluation confirms that young people in Courageous programs strengthen their confidence, academic engagement, and life skills like teamwork, responsibility, and leadership. Over the decade or more that Courageous kids spend with us, they build skills that will take them far beyond Boston Harbor.

2023 Corporate Challenge Registration

1 Boat - $5,000
At this level, your team sponsors 8 children for 1 week. 2-4 team members can participate in 4 nights of racing. Corporate Challenge teams will have their logo displayed on a jib sail, access to the fleet, and discounts on lessons. 
2 Boats - $10,000
At this level, your team sponsors 16 children for 1 week. 4-8 team members can participate in 4 nights of racing. Corporate Challenge teams will have their logo displayed on two jib sails, access to the fleet, and discounts on lessons. 
3 Boats - $15,000
At this level, your team sponsors 8 children for a full 3- week session. 6-12 team members can participate in 4 nights of racing. Corporate Challenge teams will have their logo displayed on three jib sails, access to the fleet, and discounts on lessons. 

A small fee is included for credit card transactions to cover the processing fee.

Payment Information

Pay by Check
Make checks payable to:
Courageous Sailing
197 8th Street
Charlestown, MA 02129
Pay by ACH Transfer

Submit this form and then contact Jennifer Bodde by phone or email for ACH Transfer details.

Office: (617) 237-6916  |  Email: