Saturday, 01 December 2012 10:50

Staff - Kate

Kate Henderson -  Director of Youth Programs
Kate is responsible for managing all of our need-blind youth progams. From after-school programs to our Summer Youth Program, Kate manages nearly 65 instructors and other staff to allow nearly 1,200 youth to sail with Courageous each year. Kate learned to sail on the South Shore in Cape Cod Mercuries and went on to sail in high school and college. She has worked at and managed numerous sailing programs in the area.
Saturday, 01 December 2012 10:49

Staff - Cha

Cha-ling O'Connell -  Membership and Sales Manager
Cha grew up sailing, racing, and instructing at Courageous before heading off to M.I.T., where she majored in Comparative Media Studies and sailed for the Engineers as captain of the Women's Sailing Team. For the past several years, first as an assistant program director and then as our Director of Adult Programs, Cha has been instrumental to the success of the Courageous adult program. While fostering an active and open environment for a growing community, she has also improved the training and management of staff and instructors, and refined the many scheduling and database systems that support our programs. This season, Cha's role as Membership and Sales Manager will mark her last season as one of our core staff, but she looks forward to being a part of the Courageous community for years to come!
Saturday, 01 December 2012 10:39

Staff - Dave

Dave DiLorenzo - Executive Director
Dave started at Courageous in 2007 as the youth program race coach, before becoming the director of the Courageous adult program from 2007-2011. In that time, Dave oversaw the growth of our adult membership, instruction and racing programs, helping to establish Courageous as one of the leading nonprofit keelboat schools in Massachusetts.  As our Executive Director, Dave now works closely with our Board of Directors and management team to ensure Courageous is meeting our mission and delivering the strongest and safest possible programs. Each Spring, Dave returns to his Courageous roots as coach for the Boston Latin School HS team.  Dave learned to sail on the south shore of Long Island, and is a US Sailing Keelboat Instructor and Level 2 racing coach.  
Friday, 30 November 2012 15:46

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Thank you to our donors

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Wednesday, 28 November 2012 16:45

About Courageous

About Courageous


Our Mission

Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth and leadership.

Our Vision

Courageous Sailing is a community that embraces sailing as a platform for life-long learning, personal growth and leadership; a center of sailing excellence committed to removing barriers to access for all Boston youth, the public and people with physical and intellectual challenges.


Courageous Sailing was established in 1987 as a 501(c)(3) non-profit in a joint effort between the City of Boston Parks and Recreation Department and the late South Boston sailing enthusiast Harry McDonough.  Courageous Sailing has since grown into a dynamic, multi-faceted educational facility serving over 1,000 at-risk and disadvantaged children each year.  Through the organization’s Courage Curriculum, young sailors develop essential leadership competencies in personal responsibility, communication, problem-solving, teamwork and stewardship.  Demand for Courageous Sailing’s programs is at a record high with close to two-thirds (600) of the eager young children who attempt to register for our summer program being turned away due to a lack of sufficient capacity.

How Courageous Got Its Name

The America's Cup 12 meter "Courageous" once lived at Pier 4 in the Navy Yard. This two-time America's Cup winner lent its name to Courageous Sailing in the late 1980s. The boat now resides at the Museum of Yachting in Newport, Rhode Island, where it has been restored and is still being raced.

Community Service

Courageous prides itself on being a leader in community service. Courageous has hosted the Special Olympics Summer Games and has been consistently involved in training Special Olympics athletes. Courageous also has an ongoing partnership with The Carroll Center for the Blind, which holds national blind sailing competitions as well as weekly Sail Blind races at Courageous. In addition, Courageous serves as a venue for local high school sailing team practices, as well as Women's Keel Boat and Mass Bay elimination events. Courageous has also partnered with Adventure Sail through the Big and Little Sisters organization, an event that has drawn hundreds of women and girls into the sport of sailing.

A True Public/Private Partnership

Courageous' success has captured the imagination and sponsorship of small and large Boston companies as well as hundreds of paying adult members. Corporations support Courageous' activities through the Courageous Challenge and Corporate Sponsorships, while individuals can contribute by simply becoming a member or attending exciting fundraising events such as Make-A-Mark and the College Bowl. The generous and enthusiastic contributions made by these organizations and individuals are vital to the continued growth and success of Courageous.

Courageous has also found other ways to leverage its success and appeal. In 1998, the Center sponsored the first of several co-fundraising regattas with the American Cancer Society. Our staff and venue helped them raise over $70,000 for a cure. The center continues to look for ways to help other charities while bringing the benefits of sailing to more and more children and adults.

Wednesday, 28 November 2012 15:19

Jamaica Pond Hours & Availability

Hours of Operation - April 13th - October 31st, 2013

Monday - Friday       11:00 A.M. - 7 P.M.
Saturday & Sunday  11:00 A.M. - sunset
Courageous may suspend operations or close early due to a weather event. Check our Facebook Page for updates.
Availability: Boats may be rented whenever the Youth Program is not active. The 2013 Youth Program will run Monday - Friday, 9am to 3:45pm in July and August. On weekends during the season, it’s usually best to call ahead.
Rates:     Rowboat rentals are $10 per hour ($5 per hour with a fishing license).
Kayak rentals are $12 per hour.
Sailboat rentals are $15 per hour.
Private sailing lessons are $45 per hour. Lessons must be scheduled at least one week in advance with the Boathouse
Tuesday, 27 November 2012 16:11



Thursday, 08 January 2009 10:59

Group Teambuilding

The day begins with a two-hour lesson so everyone can learn to sail and work together. After an onshore break for lunch, participants go back out on the water for several brief, fun races.

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.

The “College-style” Team Racing Event: This event is great for larger groups, as it allows several divisions to compete at alternating times. Each team has teammates on the water throughout the day, giving everyone a chance to win.

Catering: We work regularly with food and beverage catering companies and would be happy to recommend one that is familiar with our facility and never fails to provide outstanding service.


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