Frequently Asked Questions


Swimming Requirement

Summer Program Registration

Picking the appropriate "Step" or Level

Student age

Student's place of residence

Registering students together for the same class

What happened to the Summer Sailing Program at UMass/Dorchester?

I was registered! What are my responsibilities

I was waitlisted? What does that mean?

Fees and Scholarships

What to wear and what to bring to class

Does my child need a life jacket

Private Lessons

Program Locations


How do I know my child is going to be safe at Courageous?

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 through the dock gate without a life jacket.
    2. All of our head instructors are US Sailing Instructor Certified and all have attended Courageous pre-season 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.

Do you need to know how to swim?

Yes. Though swimming is not a regular part of our program, for safety reasons, all students must be able to swim, any stroke, 75 feet (or 25 yards, the length of most pools) and tread water for 90 seconds.
All new Summer Youth Program students must supply a Courageous Proof of Swimming Form (download here) or a letter on pool or organization letterhead stating that the student has met or exceeded our swimming requirement. This document must be signed by a certified lifeguard.



How do I register my child?

Registration forms for 2014 will be available March 10, 2014. For more information, visit the summer youth program registration page.

How can I get a registration form and/or brochure?

We strongly prefer that all youth program applicants use our online registration form. The 2014 Summer Program online registration form will be available between March 10 and March 28.  Click here to access the 2014 Summer Youth Program Lottery Registration Form between those dates.

Which Step should my child register for? 

Step 1: Sailing 101

If your child has no sailing experience, has only a summer or two of exposure to sailboats, or has not yet completed their Courageous "Blue Book", then Sailing 101 is probably the right place to start. In Sailing 101, instructors are right in the boats with the students at all times, which makes for a safe and highly individualized learning environment. If you are unsure of whether your child is ready for the next level, it is often best to assume they ought to stay in Sailing 101. Review is never a bad thing! Typically, students spend multiple summers in Sailing 101. If you have any more questions, please feel free to email or call.

Step 2: Beginner Sailing (minimum age 9)

This program is not available to the general public. Due to extremely high demand, this program is limited to only those youth who have already participated in a Courageous Sailing summer program at Charlestown, Jamaica Pond or Camp Harbor View.  No exceptions.  This is a three-week program that delves into greater depth on topics covered in Sailing 101.  Instructors are in the boats with students at all times.  Most students require 2-3 summers of this course before moving to Step 3.

Step 3: Intermediate Sailing (minimum age 10)

Appropriate for those sailors who are capable of comfortably sailing a small keelboat (one of our 19-foot Rhodes 19s) without an instructor with them in the boat. The Step 3 sailor knows and is comfortable with the basics (tacking, jibing, man overboard recovery, docking, rigging, knots, upwind sailing, etc.) but still needs time to review and gain mastery. The Step 3 sailor is comfortable enough with basic skills to begin applying them in on-the-water games and drills, races, and occasional trips beyond the inner harbor. Typically, students spend at least 2 to 4 sessions (one or two summers in Step 3 before progressing to Step 4).

Step 4: Advanced Sailing (minimum age 12)

For advanced sailors only, or those students who have mastered the basics and have some basic idea of sailboat racing and basic navigation. Racing students will be in dinghies for their first time (small sailboats with centerboards instead of keels). These dinghies, unlike the Rhodes-19 keelboats, are capable of capsizing, and so students MUST have comfort in the water. Cruising students will be on larger cruising boats. Both dinghies and larger cruising boats demand mastery of the basics in order to be successfully sailed. If your child has sailed with Courageous in the past, entering Step 4 students would have passed the intermediate sailing test and/or have a recommendation on file for promotion from their instructors. Typically students spend 4 to 6 sessions in Step 4 (2 to 3 summers).

The Step 5 "Instructor-in-Training" or "IIT" Program

For advanced sailors only, specifically those students who have had significant exposure to racing and/or cruising and aspire to become instructors. IITs must apply by February to be considered for selection into the summer IIT program. The selection process is competitive, with a written application, an in-person interview and a sailing skills check. The program is NOT limited to past Courageous students.

Is my child ready for Step 3: Intermediate Sailing?

For more details, see the above answer to "Which Step should my child register for?"  If in doubt, (1) ask your child if they took/passed the "Step 3 Entry Test," (2) consider whether you believe your child is sufficiently mature to be in a boat without an instructor aboard, (3) email Kate Henderson, Director of Youth Programs.

Is my child ready for Step 4: Racing and/or Cruising?

For more details, see the above answer to "Which Step should my child register for?"  If in doubt, (1) ask your child if they took/passed the "Step 4 Entry Test," (2) email Kate Henderson, Director of Youth Programs.

My child has taken sailing lessons at another sailing center. Which Step should he or she register for?

For more details, see the above answer to "Which Step should my child register for?"

Rembember: Step 2 is not open to the public. The minimum age of entry for Step 3 is 10, and students will be sailing aboard boats, without instructors, on Boston Harbor. While many children have sailed on boats, alone, at other venues, consider that Boston Harbor is one of the buisiest commercial ports in the US and that Courageous Sailing utilizes large, heavy keelboats and not the Optis, Sunfish, Bugs, Open-Bics, Mercurys or other small dinghies common to most other youth sailing programs around the state  and country. Courageous Sailing's standards for safety and requirements for sailning alond are necessarily much higher than in other sailing programs.  Again, the safety of your children is our utmost concern.

How old do my children have to be?

Step 1: All children must be at least 8 years old by the first day of class. No exceptions.
Step 2: Minimum age: 9 years old
Step 3: Minimum age: 10 years old
Step 4: Minimum age: 12 years old
Step 5: Minimum age: 15 years old (While 14 year olds may legally work in the Commonwealth of Massachhusetts, City of Boston teen employment programs, of which Courageous is a beneficiary, set the minimum age at 15.)

Do you ever make exceptions on student's age?


I am not from Boston. Can my child register for your program?

Yes. Though most of our students are Boston residents, our students hail from all corners of the greater Boston area. Our summer program is open to all.

I am not from Boston. Can my child register to sail at Jamaica Pond?

No. The Jamaica Pond site is open to residents of Boston only.

Can my children sail together in the same class?

While we try our hardest to place siblings in the same classes at the same sites, unfortunately we do not have the capacity to guarantee that siblings will be placed together. However, after a confirmation of registration has been received students and parents are welcome to call to make changes to their registration form, provided space is available.

Can my child sail with his/her friends in the same class?

Unfortunately, as we receive thousands of applications for our summer program, we cannot accommodate individual requests to place groups of friends in the same class.

Can my child register with his/her friends in the same class or at the same site?

Yes, groups of friends can try to request the same class-slots (same class, same session, same time, same site), but, unfortunately, as we receive thousands of applications for our summer program, we cannot accommodate individual requests to place groups of friends in the same class.

What happened to Courageous' Summer Sailing Program at UMass/Boston on Dorchester Bay?

In 2011, the UMass Dorchester site was closed and consolidated back to the Courageous mothership at Pier 4 in Charlestown.
While we respect that the UMass location was a geographic convenience, we hope that the positive changes including an optional extended day (8 AM to 5 PM) and intermediate/advanced programs that run for 3 or 6 weeks in all kinds of weather will keep you and your family at Courageous for the coming season.

I was registered. What are my responsibilities?

Due to the extremely high demand for this program, attendance is required at all registered classes. If for any reason your schedule changes and your child cannot attend any of the sessions s/he is registered for, please notify Courageous immediately at (617) 242-3821 x12, so that another child can be given an opportunity to participate.
If your child does not attend the first day of any program (without prior notification) then your child’s space will be given to someone on the waiting list for the remainder of the week. If your child is enrolled for multiple weeks and misses one whole week (without prior notification), all his/her remaining weeks will be given to children on the waiting list.This may also jeopardize the offending students enrollment in future seasons.The Youth Program Staff and the hundreds of waitlisted applicants thank you for your consideration and cooperation.

I was waitlisted!  What does being waitlisted mean?

If you were waitlisted, this means that the class you requested is currently full. In the event that a registered student decides they do not want their spot, the spot is opened up to a waitlisted student.

What Being “Waitlisted” at positions 1 – 5 Means

If you have a waitlist number between 1 and 5, there is a fair chance (~50% or better) that a space might become available to you, and we invite you to stop by in person the morning of the class you were waitlisted for to see if a space becomes available.  If a space becomes available and you are already at the site, you may hop into the class that morning.  If no space becomes available, then you will have to head home.

What Being “Waitlisted” at positions 6+ for Means

If you were waitlisted at position 6 or higher, it is very unlikely (~20% chance or worse) that a space might become available to you, and so we encourage you to make other summer plans.

I’m Waitlisted, but my family and I still really want to Sail!!

For the families of all youth program applicants (whether registered or waitlisted) Courageous Sailing is offering large discounts on courses through the Courageous Adult Program. For more information, please contact our Director of Adult Programs (



2014 Fees and Scholarships

Why is Courageous charging fees?

It costs about $650 per week per student to run our Summer Youth Programs. We value the diversity of population that chooses to be at Courageous.  It is important that we focus the efforts of our donor base to provide funding for those who cannot pay.  Longer term we want to develop the capacity to serve the long waiting list for our program

How was the sliding scale developed?

Courageous staff members researched comparable program costs and local income levels before setting the new fee structure.  We maintain our commitment to provide the Courageous experience to all our constituency, and no child will be turned away for financial reasons.

Is there a sibling discount?

Yes, additional children from a single household will be eligible for a 10% discount.

Do I need to be “approved” for a reduced fee scholarship?

Anyone who fits the household income requirement for a “reduced fee” will be granted a scholarship with proof of income. Click here for more information on our youth program fees and sliding scale.

Income information is sensitive. Who sees this information?

Income information for people requesting a scholarship will be seen only by the senior program administrators at Courageous.  This information will be grouped together to report overall program demographics; however, individual records are kept confidential and are not available to anyone outside the Courageous organization.
When you are admitted to the program, you will receive a scholarship form and instructions. No family is turned away that fits the requirements. Full scholarships (free classes) are available to families on government assistance or with a household income of $65,000 or less. Half scholarships (50% off classes) are available to families with a household income between $65,000 and $100,000).

My household income is above the sliding scale income levels; however due to special circumstances I cannot afford the fee.  What should I do?

If your income puts you in a fee bracket that you can’t afford, we will work with you to make sure that your child(ren) will be able to attend.

When do I send payment?

The payment process is designed to be simple.  Once you are notified that your child has been successfully registered, you will be instructed to confirm your child’s attendance by making payment by April 25th, 2014. Payment may be made online, over the phone, via mail, or in-person at our Charlestown office.

What are my payment options?

You may pay by cash, check or credit card.  Courageous accepts Visa, Mastercard, Discover, and American Express.  If you need to pay in installments, we can work out a schedule so long as the first payment is completed by April 25th and all payments are received by June 15th.



What to Bring

What should my child bring to class?

To all registered sailors, please come to class prepared with the following:
    • Plenty of water in a reusable/refillable bottle
    • Bagged lunch in a reusable lunch bag that you can bring along with you (Important: There is no guarantee that there will be time for mid-day Tedeschi's or Cafeteria trips -- you could be out picnicking on a harbor island!!)
    • Sunscreen! (though we might have a little extra to share if you forget)
    • A hat and/or sunglasses
    • A warm layer like a sweatshirt or waterproof jacket (sometimes it’s cold on the water, even in summer!)
    • A complete change of clothes (just in case you get a little wet)
    • Lots of energy and a great attitude -- be prepared to have the best time of your life!

Does my child need a life jacket?

No. While wearing a life-jacket is mandatory at all times on the docks, gangways and boats, Courageous provides life jackets to all students to borrow during their classes. Students and instructors are required to wear life jackets at all times on the docks and on the boats.

Do you offer private lessons?

Yes, on a space-available and instructor-available basis. Please call (617) 242-3821 ext. 12 for more details.




Where are you located?

Our year-round offices are located on the end of Pier 4 in the Charlestown Navy Yard, where our students sail on Boston Harbor, and at Jamaica Pond. Click here for directions
In 2008, Courageous began running a sailing program for the campers of Camp Harbor View on Long Island in Boston. If you are a Boston resident and would like more information on how to register for the Camp Harbor View program, please visit the Camp Harbor View website.

Energy on Pier 4

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're on the 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 year long! 

Summertime Sailing on Boston Harbor

The Summer Youth Program

Our Youth Program is based on a Five Step approach. Start off in Step One to get a taste of the excitement—it's only the beginning! From there, you'll work through the steps from summer to summer, having more fun and learning more than you ever thought possible on your school vacations. And in a just few years, you might very well find yourself in Step Five as an instructor!

And we're about more than just sailing. In our classes, from your instructors you'll learn a lot about the marine environment, as well as about what it takes to be a leader both on and off the water.

The best part is that your instructors are having just as much fun as you are!  Our passion is the water, and we hope it will become yours, too!

Class DescriptionsIIT Program • Summer Calendar • FAQsLottery Information

Courageous School Programs

School & After-School Programs

Expanding youth sailing in New England beyond its traditional summertime boundaries, Courageous has a growing range of spring and fall offerings. We have spring and fall programs specifically tailored to the needs of local public schools, advanced after-school programs for our summer sailors who want a little extra practice, and programs for groups of first-time sailors who want a taste of what it feels like out on the water.


After-School Sailing

This program in Jamaica Plain is open to students who have sailed with usa during the summer in Step 3 or above. This is an open time for students to practice the new skills learned over the course of the summer. Some sessions may have a specific focus, such as racing or cruising. After-School sailing is at Jamaica Plain locations.



School Programs

Courageous Sailing partners with public schools throughout the city to offer specially tailored programs that will enhance your students' experiences. These programs are offered primarily at Jamaica Plain and schools must be Boston Public Schools. Past school partners include Warren-Prescott Elementary, The Young Achievers Pilot School for Math and Science, Codman Academy, and the JP Manning School. To find out if your school can participate, email or call Kate Henderson at (617) 242-3821 ext. 12. 



High School Racing Teams

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 sail at Courageous include BB&N, Boston Latin, 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


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

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!


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.


Courageous is fortunate to have a fleet of over 50 sailboats ranging from our International Class Laser & 420 dinghies to our full-size cruising boats.  Our core Learn to Sail, day-sailing and one-design fleet consists of 27 Rhodes 19s.  For more advanced one-design racing and performance sailing we have our 8 J/22s.  See below for more information on each type of boat.

Core Membership Fleet

Rhodes 19s (27)

The Rhodes 19 is a 19 foot (6 m) long sailboat, designed by Philip Rhodes and originally manufactured by O'Day. Currently, the Rhodes 19 is built by Stuart Marine Corp. To date, approximately 3500 of the boats have been built.  Available with either a fixed keel or with a retractable centerboard, it is used primarily as a day sailer or for one-design racing.  All of the Courageous Rhodes 19s are fixed keel. The Rhodes 19 is still actively raced throughout the United States, with active fleets in many Massachusetts locations.

J/22s (8)

The J/22 is a 22 foot keel sailboat designed by J boats. It is actively raced in yacht clubs in the United States and Europe.  The J/22 has a comfortable self-bailing cockpit with 7 ft. long seats and room for 4 people in the cabin to escape the rain or cold. J/22 is built for safety with buoyancy tanks and offshore hatches. Her 700 lb. lead keel lowers the center of gravity, creating nearly 1700 foot pounds of righting moment at 90 degrees of heel.

Length overall 22.5 ft (6.98 m)
Waterline length 19.0 ft (5.8 m)
Beam 8.0 ft (2.45 m)
Draft 3.8 ft (1.18 m)
Displacement 1790 lb (812 kg)
Lead keel 700 lb (318 kg)
Upwind sail area :223 ft² (22 m²)
Spinnaker area: :345 ft² (34 m²)

There are over 1,600 J/22's now sailing in 65 active fleets in eighteen countries on three continents. Recognized by the ISAF, the International J/22 Class Association promotes activities and regattas worldwide. There is a very active class web site and association newsletters. For class racing, sails are restricted to only a main, small jib and spinnaker with total crew weight at 605 lb.

Dinghy Racing Fleet

420s (9)

The International 420 Class Dinghy is a monohull planing dinghy with centreboard, bermuda rig and centre sheeting. It is designed for a crew of two. The name describes the overall length of the boat in centimeters (the boat is exactly 4.2 meters long).  The International 420 was designed by Andre Cornu in the 1960s as a general purpose two sail, transom sheeted, non-trapeze dinghy, with modest easily handled sail plan. The hull's seaworthyness and stability at speed proved to be better than most of its contemporaries, and this together with its modest sail area make it fun to sail in heavy weather and thus an excelent youth trainer, qualities that lead to its adoption for that role by the RYA in the mid 1970's.

Lasers (12)

Thanks to the generosity of the Courageous Community, we acquired a fleet of 12 brand-new Lasers in 2010, complete with Full, Radial, and 4.7 Rigs. The International Laser Class sailboat, is a popular single-handed, one-design class of small sailing dinghy. The design, by Bruce Kirby, emphasizes simplicity and performance. Now manufactured by Laser Performance, the Laser is one of the most popular single-handed dinghies in the world. As of 2011, there are more than 250,000 boats worldwide. A commonly cited reason for its popularity is that it is robust, simple to rig and sail. The Laser also provides very competitive racing due to the very tight class association controls which eliminate differences in hull, sails and equipment.

Cruising Fleet

Ranger 23s (2)

The Ranger 23 was the first US boat to be specifically designed to the Quarter Ton Rule (MORC). Gary Mull’ s design proved to be a fast and able club racer and a good small coastal cruiser. It was produced with both tall and short rigs. At 3,394 lbs. , it carried 264 sq ft of sail. Gary Mull, said that “the intention was to produce a little ship capable of sailing anywhere in the world safely and swiftly.” The first boat was build in 1971 and the last in 1977 (739 total).

The Ranger 23 is probably the best sailboat in its size range ever built. This 1971 design has served its owners well through the years and is still sailing strong. The boat was made famous as the central character in the movie "The Dove" about young Robin Lee Graham’s solo circumnavigation. (note: Dove was a 24 ft. Lapworth design built about 1960 - the movie used a R23).


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