Friday, 06 February 2009 02:07

Step 2: Beginner

Age 9 and up
Swim Requirement Must supply proof of ability to swim 75 feet and tread water for 90 seconds. Download our Proof of Swimming Ability Form here.
Experience Requiment Open only to students returning to Courageous who have already completed at least one summer of Step 1, "Swim-Sail-Science," Camp Harbor View, or Summer Learning Project
Limits One 3-week session per child per summer.
2015 Dates
  • Session 1: Mon 7/6 - Thu 7/23 (weekdays, 9:30 AM - 3:30 PM)
  • Session 2: Tue 7/28 - Fri 8/14 (weekdays, 9:30 AM - 3:30 PM)

*drop off begins at 9:15 AM; extendedday option available (see FAQ)

Locations Charlestown only
Cost $550 (fee is based on a sliding scale; 10% off for siblings)

Course Description

Step 2 is a Beginner Sailing course offered to children ages 9-and-up from throughout the Greater Boston Area who are interested in learning more about sailing. Each session of Step 2 lasts three weeks, and students typically repeat this Step for a number of summers. During this time, they develop fundamental sailing skills, in preparation for more independent sailing in Step 3.

Please note: Due to high demand, enrollment in Step 2 is strictly limited to those who have already participated in one of the Courageous Summer programs. Please refer to the registration and FAQ section for more details.

Friday, 06 February 2009 17:04

Step 1: Sailing 101

Age 8 and up
Swim Requirement Must supply proof of ability to swim 75 feet and tread water for 90 seconds. Download our Proof of Swimming Ability Form here.
Experience Requiment No experience necessary. New sailors welcome.
Limits One session per child per summer. Each session is 4 days long.
Daily Schedule

9:30 AM - 3:30 PM*

*drop off begins at 9:15 AM; extended day option available (see FAQ)

2015 Dates


  • Mon 7/13 - Thu 7/16
  • Mon 7/20 - Thu 7/23
  • Tue 7/28 - Fri 7/31
  • Mon 8/2 - Thu 8/6
  • Mon 8/10 - Thu 8/13
  • Mon 8/17 - Thu 8/20 (Charlestown residents only!)


Jamaica Pond (Boston residents only - proof of residency required!):

  • Mon 7/13 - Thu 7/16
  • Mon 7/20 - Thu 7/23
  • Tue 7/28 - Fri 7/31
  • Mon 8/2 - Thu 8/6
Locations Charlestown and Jamaica Pond
Cost $200 (fee is based on a sliding scale)

Course Description

Step 1 is our "Sailing 101" course, offered to children ages 8-and-up from throughout the Greater Boston Area. Each student attends Step 1 for one four day session. During this time they are introduced to the basics of sailing theory and are exposed to boating on Boston Harbor. Students are taught through a fun, high-energy, game-based approach, learning aboard stable keelboats, Rhodes-19s. No prior sailing experience necessary, though all students must be able to demonstrate a minimum level of swimming competency. Please refer to the registration FAQ section for more details. At Jamaica Pond, students will use a combination of rowboats, small sailboats, and kayaks.


Sunday, 01 February 2009 21:23

Commitment to Safety

Commitment to Safety

At Courageous we place tremendous importance on safety. We are constantly taking measures to impress upon our students that a safe sailor is a good sailor. Below is a partial listing of our safety regulations, rigorous guidelines that have given Courageous one of the best safety records on Boston Harbor.

  1. Life jackets must be worn at all times while on the dock. No student is allowed throug the dock gate without a life jacket.
  2. Most of our instructors are US Sailing Instructor Certified and all have attended Courageous training programs.
  3. A head instructor is always on duty to supervise operations.
  4. A safety launch accompanies all classes with at least one launch on stand-by at the Courageous pier.
  5. Our student-to-instructor ratio is 3:1 — one of the best in the industry.
  6. All launches are equipped with VHF radios for fast communication with each other, the boathouse, and if necessary the Boston Harbor Police and US Coast Guard.
  7. Courageous has a conservative foul weather policy. Boats are recalled or kept at the dock in bad weather and forecasts are monitored constantly.
  8. All students in the program must be able to swim at least 25 yards and tread water for 90 seconds.


Sunday, 01 February 2009 20:57

After School Sailing

After School Sailing

Sunday, 01 February 2009 20:56

Schools and Youth Groups

Schools and Youth Groups

Sunday, 01 February 2009 20:54

High School Racing


Several competitive high school sailing teams train at Courageous' sites in Charlestown or Jamaica Pond. Whether a school is putting together a team for the very first time or has an already established team that needs a new place to sail, Courageous has been able to come through for local schools.


Current high schools that train with Courageous include BB&N, Boston Latin, The British School of Boston, Codman Academy Charter Public School, and Boston Public Schools (district-wide team). To find out if your high school can participate, email or call Kate Henderson at (617) 242-3821 ext. 12.


Boston Public Schools' District-Wide Sailing Team
Thanks to an outpouring of community support, in March of 2011, the BPS district-wide sailing team took the water for the first time with a small, but extremely dedicated crew of sailors. The team was comprised of students from all parts of Boston. They had one thing in common: a passion for sailing. The season culminated in a strong C-Division finish at the Mass Bay League Championship. The team’s success was highlighted in numerous news articles, and we were honored that it received national praise in the Council for Great City Schools’ June/July 2011 issue of Urban Educator.

Now entering their second season, returning team members, under the tutelage of veteran Courageous coach Chris DuBois, will return to lead a larger Varsity program and set the stage for a new JV team.



BPS Students: Interested in Sailing for Boston Public?

**Note: If you attend Boston Latin School, this isn't for you -- you already have a team. Contact Dave and Cha -- they're your BLS sailing coaches!

  • Requirements:
    • No sailing experience necessary!
    • Must be able to swim the length of a pool, unassisted, any stroke, and tread water for 90 seconds.
    • Must be able to commute to Charlestown Navy Yard in time for 3:45 (practice start time) and provide own transportaiton home.
  • Sailing Season Dates: March 26 - June 3, 2012 (tentative)
  • Practice Times: Monday, Wednesday, Friday, 3:30 pm - 6:30 pm
  • Practice Location: Courageous Sailing, Charlestown Navy Yard (directions)
  • Waiver Forms: Download here. Must be signed by parent/legal guardian in order to participate.
  • Medical Forms: Download here. Must be completed and signed by a parent/legal guardian in order to participate.
CYRT 2008

Courageous Keelboat Kickoff Regatta, 3/31 - Registration Deadline: Monday, 3/26

First Event of Mass Bay League B Division Fleet Race Series

Please join us for the 4th Courageous Keelboat Kickoff Regatta. The event is a great opportunity to get a lot of kids on the water, early in the season.

Please note:

  • Skippers must be able to sail a Rhodes 19keelboat comfortably and safely in tight quarters, onto and off of a fixed dock.
  • Each "slot" represents 6 sailors (3 in A div, 3 in B). At full capacity (20+ Rhodes 19s) we can accomodate 120+ sailors.
  • This event is open to all MBL and NESSA teams, with 2 slots reserved for each MBL B-Div team.  Registrations will be taken in the order they are received.  All schools may register a second or third team, but these will be waitlisted until the registration deadline, Monday, 3/26. 

The NOR is below.  Let me know if you have any questions, and please register early.

Dave DiLorenzo
Boston Latin School Head Coach

Notice of Race

2012 Courageous Keelboat Kickoff Regatta (First Event of Mass Bay League B Division Fleet Race Series)

Date: Saturday, March 31, 2012
Location: Courageous Sailing Center, Boston Harbor

Report Time: 0900
Boats: Rhodes 19 Keelboats (3 person crews)
Format: A and B Division
Rules: RRS, ISSA PR, NESSA PR and By-laws, including Article L
Registration Deadline: Monday, March 26, 2012 at 1700 hours

Registration: To register, send an email to Cha OConnell that includes the following information:

1. Name of school
2. Contact info for the coach (phone, email)
3. Number of slots.  (Schools may request any number of slots. MBL B division teams requesting more than 2 slots, and all other teams requesting more than 1 slot, will be kept on the waitlist until after the registration deadline, at which time they will be added in the order they were received, one per school, until all slots have been filled.)
4. In subject line please put "Courageous KeelboatKickoff/School Name"

Waiver Forms:
Team members and coaches must complete the following waiver forms and submit at check-in on raceday. Please download and complete in advance to save time:
Friday, 09 January 2009 13:33

Basic Keelboat Part 1

Basic Keelboat Part 1

12 hours

Whether you're totally new to sailing or haven't sailed in a while, our BK Part 1 course is a great way to give sailing a try without a big commitment! If you like it, come back for BK Part 2 (in our Charlestown Boston Harbor site) and work towards your US Sailing Basic Keelboat Certification.
Prerequisite: None
Included text: US SAILING Basic Keelboat.
For more information about courses, or to purchase and schedule a course, please email Mike Kostigen, Jamaica Pond Site Director or call the JP Boathouse directly at 617-522-5061

Thursday, 08 January 2009 10:46

Youth Program Locations

Youth Program Locations

Courageous sails out of three locations in Boston - Charlestown Navy YardJamaica Pond, and Camp Harbor View (on Boston's Long Island). 

Reefing during the Summer Youth Program in Charlestown


Our Charlestown facility operates year-round and houses our executive, administrative and program staff. This location processes registrations and leads our fundraising and program development efforts. The Courageous Boathouse is located on Pier 4 in the Charlestown Navy Yard, a short walk from North Station, the Bus Route 93 Navy Yard/Gate 4 bus stop, or the Long Warf F4 water shuttle that departs near the Blue Line's Aquarium T station.

Jamaica Pond

Courageous is pleased to offer youth and adult sailing on Jamaica Pond in cooperation with the Boston Department of Parks and Recreation. The summer youth program at Jamaica Pond is open to Boston residents only. The Jamaica Pond Boathouse is located at the intersection of the Jamaica Way and Pond Street, 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. More info on Jamaica Pond.

Camp Harbor View

Courageous now operates a summer sailing program for campers at Boston's Camp Harbor View on Long Island. For more information on the camp, visit, or visit the Boys and Girls Club of Boston at

Thursday, 08 January 2009 10:45

Youth Programs

The Courageous Youth Program

Never been sailing? No problem: get ready for the ultimate adventure!


In just one lesson you'll be out on the water. If you like it—which we're sure you will—before long you'll be skippering a boat, racing on a team, or cruising around the harbor islands. If you stick with it, one day you could even be a Courageous instructor! While you'reonthe water, you're going to learn lots about the environment, and get to practice some pretty important life skills, too. From fishing off our pier to overnight island camp-outs, we'll keep you having fun on adventure after adventure, all summer long!
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