The Courageous Corporate Challenge brings teams from businesses in and around Boston to race on company-sponsored boats on Boston Harbor. They take part in the name of friendly competition and in support of Courageous Sailing’s Summer Youth Program.

Courageous Challenge Charity Regatta

The Challenge is delayed, but the time for your company's support is now.

The warm weather and late sunsets of late May and June usually herald the Courageous Corporate Challenge, in which seasoned and novice racers alike set sail from Pier 4 in the Charlestown Navy Yard each Monday evening for some fast-paced, college-style, short-course keelboat racing. This year, however, COVID-19 and social distancing regulations have compelled us to postpone this annual celebration of corporate camaraderie and the sport of sailing, though we hope to bring the Challenge fleet together on the water before the end of the season.

While we can't yet gather for nights of racing followed by food and drinks under the tent, your company's support is needed now more than ever. We are committed to being there for Courageous kids as soon as they can safely get back out on our boats, and to fostering their emotional and learning needs as they adjust to the "new normal." We hope that you will join us in making this possible by committing to one or two Courageous Corporate Challenge boats. Your generosity supports our mission, our programs, and our Courageous kids.

2020 Schedule


2019 Results

View Results

2019 Race Documents


Your Impact

The work Courageous does has never been more vital, and we have never needed the generosity of our donors more, in order to keep the Courageous experience available to all.

At Courageous, our goal has always been for every student who sails, swims, and learns with us during the summer to return to school ready, engaged, and eager for more. This will be more important than ever this year. Courageous programs have a proven track record of helping youth improve academic competencies and strengthen social-emotional skills, such as teamwork, responsibility, leadership, and self-reliance. This expertise makes us ideally situated to help mitigate the effects of the seclusion, learning loss, and emotional trauma that many of our children are now experiencing.

This year, while all of the members of our community are dealing with social and economic upheaval, we are especially concerned that our Courageous kids and families from vulnerable, low-income, and marginalized households will be acutely and disproportionately affected by the pandemic. Central to the Courageous mission has always been a commitment to those in greatest need—we provide free meals, transportation, and a leadership team with the social work training and experience—to ensure that our academic, sailing, and swimming classes remain accessible, and that every child has the support they truly need.

Join the Fun

Use your company’s Challenge boat as a weekly perk for employees (Courageous will be happy to provide an expert skipper) to race around the harbor, or commit a dedicated team to the cause and try to win it all. Either way, it’s sure to be a fulfilling way to spend a Monday evening while supporting Courageous’ mission.

With one boat, a Challenge team can have 2-4 team members participate for the 5 weeks of racing; two boats accomodates 4-8 team members for evenings of competition and fun. As always, we will also aim to provide Corporate Challenge teams with access to the fleet through our Corporate Membership and their logo on a jib sail or jib sails. Every team provides essential funding to our youth programs and young sailors.

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 nights
*Limit one boat at a time

2019 Courageous Challenge Charity Regatta Results

2020 Corporate Challenge Registration

1 Boat - $4,000
At this level, your team sponsors 8 children for 1 week. 2-4 team members can participate in 5 nights of racing. As always, we will aim to provide Corporate Challenge teams with access to the fleet, their logo on a jib sail, and discounted lessons.
2 Boats - $7,000
At this level, your team sponsors 12 children for 1 week. 4-8 team members can participate in 5 nights of racing. As always, we will aim to provide Corporate Challenge teams with access to the fleet, their logo on a jib sail, and discounted 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
One First Ave.
Boston, MA 02129
Pay by ACH Transfer

Submit this form and then contact Mackenzie Spellicy by phone or email for ACH Transfer details.

Office: (857) 452-1759  |  Email: