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

At Courageous we place a 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 list of our safety regulations; our rigorous guidelines 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 and in boats. No student is allowed through the dock gate without a life jacket.
  2. Every instructor and staff member is at least First Aid and CPR certified.
  3. All of our head instructors are US Sailing Instructor Certified and all have attended Courageous pre-season training programs.
  4. A head instructor is always on duty to supervise operations.
  5. A safety launch, or safety boat, accompanies all classes with at least one launch on stand-by at the Courageous pier.
  6. Our student-to-instructor ratio for our beginner sailors is 3:1 —one of the best in the industry.
  7. 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.
  8. Courageous has a conservative foul weather policy. Boats are recalled or kept at the dock in bad weather and forecasts are monitored constantly.
  9. Students must be able to swim at least 25 yards and tread water for 90 seconds in order to sail.

Does the student need to know how to swim?

Yes. Though swimming is not a regular part of our program, for safety reasons, students must be able to swim, any stroke, 75 feet (or 25 yards, the length of most pools) and tread water for 90 seconds.

New Summer Youth Program students must supply a Courageous Proof of Swimming Form (download here) signed by a certified lifeguard; a letter on pool or organization letterhead stating that the student has met or exceeded our swimming requirement; or proof of swimming at one of the following levels:

  • YMCA: Certificate of completion for Fish Level and/or Level 5 or above
  • Red Cross: Certificate of Completion for Level V or above
  • Boy/Girl Scouts: Swimming or Lifesaving Merit Badge


How do I register my child?

For the Steps To Lead program we rely on a lottery to provide equal access to all families. The lottery will be open from February 1 – 15, 2023. Enter the lottery via a link that will be posted on our website when the lottery is open. Families will be notified in early March, 2023 if their child has received a spot in the program, or if they have been placed on the wait list. Families that have received a spot must confirm their registration by March 30, 2023. As spots become available, families on the wait list will be notified.

For Swim Sail Science, registration is limited to students from participating schools. To find out more about SSS registration, please contact our Youth Program team at For more information, visit the How to Sign Up page.

Which Step should my child register for?

Current Courageous Sailing students receive a recommendation of which Step they should register at the end of each summer. Parents of current students who are unsure which Step their child is eligible for should contact our Youth Program team at

Step 1: Sailing 101 (minimum age 8)

If your child has no sailing experience or is new to Courageous, then Step 1: Sailing 101 is probably the right place to start. In Sailing 101, instructors are 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 Steps to Lead or Swim Sail Science Courageous Sailing summer program. 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 11)

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 one or two summers in Step 3 before progressing to Step 4.

Step 4: Beginner Dinghy (minimum age 12)

For advanced sailors only, or those students who have mastered the basics. Students will be in dinghies for their first time (small sailboats with centerboards instead of keels). These dinghies, unlike the Rhodes-19 keel boats, are capable of capsizing, and so students MUST have comfort in the water. If your child has sailed with Courageous in the past, entering Step 4 students would have a recommendation on file for promotion from their instructors. Typically students spend 1 to 2 summers in Step 4.

Step 5: Advanced Dinghy or Cruising Sailing (minimum age 13)

For advanced dinghy or cruising sailors only. Dinghy students will be in higher performance dinghies including Lasers and 420s. 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 5 students would have a recommendation on file for promotion from their instructors. Typically students spend 2 to 3 summers in Step 5.

The Step 6 “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 before March 1 to be considered for selection into the paid summer IIT program. The selection process is competitive, with a written application, an interview, and a sailing skills check. The program is NOT limited to past Courageous students.

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?”
Remember: Step 2 is not open to the public. The minimum age of entry for Step 3 is 11, and students will be sailing aboard boats, without instructors, on the Boston Harbor. While many children have sailed on boats, alone, at other venues, please consider that Boston Harbor is one of the busiest 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 sailing alone 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: 11 years old
Step 4: Minimum age: 12 years old
Step 5: Minimum age: 13 years old
IIT: Minimum age: 15 years old (While 14-year-olds may legally work in the Commonwealth of Massachusetts, City of Boston teen employment programs, of which Courageous is a beneficiary, set the minimum age at 15.)

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

For our Charlestown site, 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 with the exception of Jamaica Pond, which is funded by the city and open to Boston residents 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, 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 or email our Youth Program team at to request changes to their class assignments, provided space is available.

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

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

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 the sessions s/he is registered for, please notify Courageous immediately at (857) 452-1769 or, 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 waitlist 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 a child on the waiting list. This may also jeopardize the absentee student’s 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 more) that a space might become available to you. We will contact you as soon as we know that a space has become available.

What Being “Waitlisted” at positions 6+ Means

If you were waitlisted at position 6 or higher, it is very unlikely (~20% chance or less) 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 offers large discounts on courses through the Courageous Adult Program.

Fees and Scholarships

Why is Courageous charging fees?

It costs about $600 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 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.

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 scholarship 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 $70,000 or less. Half scholarships (50% off classes) are available to families with a household income between $70,000 and $140,000.

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 completing an online confirmation form and by making the payment. 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.

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 7-11 trips — you could be out picnicking on a harbor island!! Only students in Step 4 or 5 may take trips to 7-11.)
  • 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 to provide 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 during their classes.

Do you offer private lessons?

Yes, on a space-available and instructor-available basis. Please contact our Adult Programs team at for more information.


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. We also operate at Jamaica Pond.