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 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.
2027 Schedule TBC
Race Night 1
Race Night 2
Race Night 3
Race Night 4 + Awards
Make-Up Day
Results, documents and contacts
Check out last year's results:
2027 Downloadable information + Race Documents
- Notice of Race (NOR)
- Sailing Instructions (SI)
- Courageous Challenge Info Packet
- Courageous Corporate Membership Info
Contact
Dave DiLorenzo dave@courageoussailing.org
Jennifer Bodde jen@courageoussailing.org
Caitlyn Ridgely caitlyn@courageoussailing.org
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 (once they have qualified as a skipper), take advantage of discounts on lessons, and participate in member events all season long through the included corporate membership. Challenge teams are invited to celebrate at Courageous's annual gala; four complimentary tickets are included with each boat. 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
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. Well 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 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.
2026 Corporate Challenge Registration
