Saturday, 15 December 2012 13:13



Courageous' first volunteer was Harry McDonough who summoned a small group of volunteers to get the resources and support necessary to create Courageous Sailing Center in 1987. Today, volunteers can help with a variety of tasks at Courageous, especially in preparation for the busy summer season. Courageous schedules "Work Parties" where volunteer work crews help Courageous prepare boats for the season, spruce up the boathouse, etc. Volunteers also contribute to our "Guest Coach" program and not only coach our racing program for a day but also talk about how sailing made a difference in their lives and careers.

Contact us to get involved as a volunteer.

Saturday, 08 December 2012 15:04

Employment - Youth Program

Youth Program Employment Opportunities

In the Courageous youth program, we strive to transform kids' lives through the sport of sailing. Our sailing school's instruction team works not only to foster students' love of sailing, adventure and the outdoors, but also to give them the values, skills and confidence that they will need to thrive in their lives beyond Courageous. The Courageous Youth Programs have opportunities for everyone from aspiring instructors to seasoned outdoor educators and youth program managers. Expand the list below to learn and apply to available positions.


Give back. Change Lives. Apply today!

To Apply: 

(1) Compose a cover letter that lists the positions you are interested in, describes your qualifications for these positions and explains why you wish to work at Courageous Sailing.
(2)  Update your resume, in a way that highlights any relevant experience in sailing instruction, sailing, teaching, coaching, working with youth, etc. Please also list and/or send photocopies of any relevant certifications.
(4) In the event that the application form is not working for you, you may also email or mail all of the above application materials to the Director of Youth Programs:


Attn: Kate Henderson
Director of Youth Programs
Courageous Sailing
One First Avenue
Charlestown Navy Yard
Boston, MA 02129
Thursday, 08 January 2009 11:07

2011 Courageous Challenge

2011courageouschallenge16th Annual

Courageous Challenge Charity Regatta

May 23, June 6, 13, 20, and 27 
6 pm to sunset

For the past sixteen years, the Courageous Challenge has been our most popular and successful corporate fundraiser.

What is the Courageous Challenge?

The Courageous Challenge is a corporate regatta and teambuilding event. By participating, your company is supporting Courageous' free programs for Boston youth, where over 10,000 children have learned to sail over the past eighteen years. Learn more about our youth programs!

How does the Challenge work?

The Challenge Regatta runs for four consecutive Monday nights (June 6, 13, 20 and 27), with a prepartory night of sailing and instruction on May 23.

The first night of the regatta is a "Racing Clinic". The evening includes practice races from 6pm to sunset. We will have coaches on hand to work with you on and off the water, all followed by fun awards and video coverage immediately following the races.

The next four nights are when the competition heats up! Each team races with their respective crews, and Gourmet Caterers provides a light buffet on the Courageous pier at sunset.
On the final night one young sailor from the Courageous Advanced Racing Program will join your team. The Challenge culminates with an awards ceremony and farewell barbecue.

No sailing experience is necessary to compete in the Courageous Challenge. If you request, our experienced and knowledgeable instructor staff will be on hand to show you everything you need to know. Also, keep in mind that the two to three people in your sailboat can change from week to week, this allows for more people to take part in the fun. But many teams have the same people racing each week.

Donation Structure

All Club levels include the application of the campany's name on one of our Rhodes 19s for the entire season.

Skipper’s Club $2,500

5 nights of racing on Boston Harbor.
Donation pays for:

15 children to attend the Courageous Learn to Sail Program.

Commodore’s Club $3,500

5 nights of racing on Boston Harbor.
Company logo in full color on the jib sail.
10 tickets to Courageous Sailing Center’s Make-A-Mark Gala.
Donation pays for:

15 children to attend the Courageous Learn to Sail Program and;
5 children to attend the Courageous Advanced Racing or Cruising Program.

Admiral’s Club $4,500

5 nights of racing on Boston Harbor.
Company logo in full color on the jib sail.
10 tickets to Courageous Sailing Center’s Make-A-Mark Gala.
Donation pays for:

15 children to attend the Courageous Learn to Sail Program;
5 children to attend the Courageous Advanced Racing or Cruising Program, and;
One teenage sailor to attend our Instructor In Training Program.

Wednesday, 14 January 2009 14:58

Directions to Jamaica Pond

JP AutumnThe Jamaica Pond Boathouse is located at the intersection of the Jamaica Way and Pond Street. Jamaica Pond is a one and one-half mile walk from the Orange Line's Green Street T Stop, and is also on bus routes 39, 41 and 48.
Jamaica Pond Boathouse, 507 Jamaica Way, Jamaica Plain, MA 02130
Wednesday, 14 January 2009 14:58

Directions to Charlestown


Click here for a Google map that shows where we are, where nearby parking is, and how to walk to us from public transport.

Physical Address: Pier 4, Charlestown Navy Yard

Mailing Address: One First Avenue, Charlestown, MA

By Car:

From south of Boston: Take Interstate 95N to Interstate 93N to Boston. Go through the new I-93 North tunnel. Stay in the right lane. Take exit (#23) (Govt. Center). Stay to the right when the exit ramp splits, towards the North End and Charlestown. Proceed straight onto North Washington Street and across the Bridge. Take a right at the end of the bridge onto Chelsea Street. Follow the directions below.

North of Boston: From 93 Southbound: Take "Sullivan Square/Charlestown" exit (#28). Go straight to set of lights. At the rotary take your second right on to Rutherford Avenue past Bunker Hill Community College. At second light, take left onto Chelsea Street. Follow the directions below.

From Storrow Drive Eastbound: Continue along the Drive until it ends at the I-93/North Station exit. Follow signs to North Station. At the lights, take a left onto Causeway St. The Fleet Center and North Station will be on your left. At the next set of lights, N. Washington St., make a left and cross the Charlestown Bridge. Make a right at the first set of lights onto Chelsea Street. Follow the directions below.

Continue on Chelsea though two sets of traffic lights. At the third set of lights, take a right into the Navy Yard. Upon entering Gate 4 of the Navy Yard, you should see red and white signs pointing you to Courageous. Take your first left on to First Avenue, and then take your first right on Eighth Street. Follow the road behind the Flagship Wharf Complex. The road will bring you right to the base of Pier 4, where we are located in the white building on the pier. There is no parking on the pier.

Take the green or orange line to North Station. Follow Causeway St. towards the North End; take a left onto North Washington St. and cross the Charlestown Bridge. Take a right at the first set of lights onto Chelsea St., and walk through the Constitution Complex along the waterfront. Take a right onto Pier 4; Courageous is the white building on the pier.

By Bus:
Bus #93 runs from the Haymarket and Sullivan Square Stations to First Avenue in the Charlestown Navy Yard. Upon getting off the bus, follow the above directions to Courageous.

Saturday, 10 January 2009 22:49

Employment - Adult Program

Adult Program Employment Opportunities

At Courageous we are committed to making the highest quality sailing education accessible to the community. We rely on instructors who are both great sailors and great teachers. If you have taught sailing before, or have wanted to, we want to hear from you!
Adult Program Instructor positions are typically part-time, with most classes running on the weekends and weekday evenings, so are often a great fit for those with "real jobs" who want to do something totally different in their spare time.  Some full time instructor positions are also available.
Saturday, 10 January 2009 22:42

Boat Donations/Sales

Boat Donations/Sales

Donated boats are typically used in our youth and membership programs and then sold after several years of use to help keep our youth sailing programs FREE.  In particular, we are looking for good quality Rhodes 19s, J/22s and larger cruising boats.  Please contact Fleet Manager Dan Keenan via email if you are considering donating a boat to Courageous.

Our inventory of boats for sale is changing all of the time.  For an updated listing of what Courageous has for sale please email Dan Keenan.

List of Boats Currently Available:

"Midnight Special" 1974 Ranger 23  ($2,000) [UNDER OFFER 11/23/11]

"Small Change" 1976 Ranger 23  ($2,000) [AVAILABLE 11/23/11]

"Clara Lee" 1970 Westerly Cirrus  ($3,000) [UNDER OFFER 11/23/11]


Friday, 09 January 2009 13:16

How To Help



Keep Courageous Kids Sailing!

Courageous Sailing—a 501(c)(3) nonprofit organization—can only continue to inspire Boston youth through sailing with help from individual donors like you.

Please consider making a tax-deductible gift today by clicking this link.

Donor Levels
• $25—Couragean • $150—Foredeck $650—1 week of Lessons for 1 Child!
• $75—Crew • $500—Afterguard • $1,000—Commodore

Ways to Give

Donations may be made online (by clicking the "Donate" button above), by phone (617-242-3821) or via mail. Mail checks to: Courageous Sailing, One First Avenue, Boston, MA 02129

Donate Your Boat

Your tax-deductible boat and/or equipment contribution will help support our Youth Programs, fleet improvements and other capital needs. For Equipment or Boat Donations, contact Dan Keenan for more info.


We welcome corporate and individual volunteers to join us serving the community. In Spring and Fall, the busiest times, volunteer parties will help maintain our fleet and boathouse. Throughout the whole year, volunteers can join us helping with events and other projects. You can also adopt a boat or serve as a guest coach. Contact Lindsey O’Connell, our volunteer coordinator, to learn about upcoming opportunities.

Attend Our Events

We host fundraising events and member events on a regular basis. We invite you to our events and meet other sailing enthusiasts in Boston area.

Work for Us

We have a range of positions in our Adult and Youth Programs and in our office. Check back often for up-to-date information.

Thursday, 08 January 2009 11:08

Richard R. Ross Regatta & College Bowl

College BowlRichard B. Ross Regatta
& College Bowl

The Regatta celebrates the life and vision of Boston's Richard B. Ross, a Dorchester native who believed in the transformative power of education. Before Richard tragically lost his life in the attacks of September 11th, 2001, he was a passionate sailor who took great pleasure in passing on his love of sailing to others. One of the ways his family continues to honor him is by providing generous support to Courageous in his name.

Courageous Sailing was proud to host the 7th Annual Richard B. Ross College Bowl Regatta, on Saturday, October 1st, 2011.

On a day when a slow moving low weather front left New England regattas becalmed and fogbound, Boston Harbor served up enough good breeze to keep 17 collegiate teams moving in Rhodes 19's for five great races. Afterward, teams gathered on Pier 4 for a barbecue. Our heartfelt thanks and appreciation goes out to the Ross family for their generous support of the regatta and Courageous Sailing. Thanks, too, to all sailors for participating; Ken Legler for being a great booster of this event, and Russ Bolt for taking so many great pictures! And congratulations to teams from Williams, Roger Williams and Northeastern for taking the top spots!

1st place/11pts, Williams College - Joshua Revkin & Isaac Loh
2nd/11pts, Roger Williams - Tucker Blagden & Andrew Vachon
3rd/15pts, Northeastern - Mike O'Brien & Carolyn Mason

The names of the participants on the winning boat will have their names inscribed onto the Richard B. Ross Memorial Trophy, which hangs in the Courageous Sailing Boathouse for perpetuity.

All funds raised by the College Bowl go directly to benefit Courageous's FREE youth programs.


Saturday, 19 May 2012 20:00

Commodores Salute

Coming Soon

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