Frequently Asked Questions

Registration for 2016 is now closed. Registration is open March 1 to March 15 each year. Please check back next year for 2017 registration.


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 2016 will be available March 1, 2016. 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 2016 Summer Program online registration form will be available between March 1 and March 15. You can access the form on the summer youth program registration page.

Which Step should my child register for? 

Step 1: Sailing 101 (minimum age 8)

If your child has no sailing experience or has only a summer or two of exposure to sailboats, then 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 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. Although several instructors are available to sail in boats with students to help them fine tune skills, the goal of Step 3 is for students to transition to sailing in a boat with 2 peers and no instructor. In 2016, students will also spend one week in smaller dinghies, which they will learn how to capsize and right. Typically, students spend at least two or three summers in Step 3 before progressing to Step 4.
If in doubt about whether your child is ready for Step 3, (1) check your child's progress report, if available, to see if their Step 2 instructors felt that they were ready to move up to Step 3, (2) ask your child if they took/passed the Step 3 on-the-water checkout (3) consider whether you feel your child is sufficiently mature to be in a boat without an instructor aboard, and (4) email the Youth Program Outreach Coordinator if you're not sure; we'll be happy to take a look at our records.

Step 4: Advanced Sailing (minimum age 12)

For advanced sailors who are comfortable independently skippering and crewing on a small keelboat. Sailors must be able to keep the boat under control and the sails trimmed correctly while maneuvering, performing a crew overboard recovery, docking, etc. Familiarity with sailing terminology is also a must. Dinghy students will be in dinghies (small sailboats with centerboards instead of keels), possibly for the first time. These dinghies, unlike the Rhodes-19 keelboats, can and will capsize, and students MUST be comfortable in the water. Sportboat/Cruising students will be on a high-performance sportboat called a J/80. Both dinghies and sportboats demand mastery of the basics in order to be successfully sailed. Typically students spend between two and four summers in Step 4.
If in doubt about whether your child is ready for Step 4, (1) check your child's progress report, if available, to see if their Step 3 instructors felt that they were ready to move up to Step 4, (2) ask your child if they took/passed the Step 4 on-the-water checkout, and (3) email the Youth Program Outreach Coordinator if you're not sure; we'll be happy to take a look at our records.

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

For advanced sailors only, specifically those students who have had significant exposure to dinghy sailing 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. Click here for more information about the IIT Program.

Should I choose Step 4 Dinghy or Step 4 Sportboat/Cruising?

It depends on what your child is interested in doing! Both groups will spend the third week of the program together sailing J/22s (and the J/80) and preparing to sail to a harbor island for an overnight camping trip, so your child will be able to spend time with friends in the other group. Sailors in the (larger) Dinghy group will be sailing closer to Courageous and will be sailing independently in a variety of small boats; they'll also get a taste of racing. Sailors in the (smaller) Sportboat/Cruising group will spend more time navigating the outer harbor and will always have an instructor on the boat with them. It's ideal to spend at least one summer focusing on each aspect of sailing before applying to become an IIT.

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 10, and students will be sailing aboard boats, without instructors, on Boston Harbor. While many children have sailed alone on boats at other venues, 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, Mercuries, 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: 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 Massachusetts, 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?

Between 2012 and 2015, Courageous was not involved with UMass Boston in Dorchester.
As of 2016, we are considering running a one-week session of Step 1 at the end of the summer, with the possibility of more programs being added in 2017 and beyond. If you're interested, please indicate this on your registration form. This will not affect your chances of being selected for a program in Charlestown or on  Jamaica Pond. We will contact interested families.

I was registered. What are my responsibilities?

  • Due to extremely high demand, the following Courageous Sailing Summer Youth Program policies are aimed at maximizing the number of students able to participate and reducing the number of children who remain on the waitlist.
  • If your schedule changes and your child cannot attend the session s/he is registered for, please notify Courageous immediately at 617-242-3821 x12 so that another child can be given the opportunity to sail.
  • Your child's spot will be given to one of the children on the waitlist if:
  • 1. Confirmation is not received by May 1, 2016
  • 2. Your child does not attend the first day of a one-week program or the first         week of a multi-week program (without prior notification). Your child's space will be given to someone on the waitlist for the remainder of that session. 
  • 3. The following paperwork has not been signed and submitted to Courageous Sailing by the first day of a student's session: Medical and General Liability Waiver, Proof of Swimming Ability Form and Confirmation Form.
  • 4. Courageous is not informed of a cancellation within two weeks of a child's program start date.  That family will not be eligible to participate in the summer youth program the following year.  If extenuating circumstances necessitate canceling within two weeks, contact Courageous Sailing immediately.

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 (



2016 Fees and Scholarships

Why is Courageous charging fees?

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 who did not receive a scholarship 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. Proof of income must be submitted by April 30.

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. Partial scholarships (approximately 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 30. Payment may be made over the phone, online, 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 30 and all payments are received by June 15. Payment may be made over the phone, online, via mail, or in-person at our Charlestown office. 



Online Payments


An invoice was mailed to you with your confirmation letter. This amount reflects anticipated scholarship amount. You can pay this invoice via credit card by using the following links.


For families with only 1 participating child please select the link that matches that on your invoice:


You can also pay by submitting a check (payable to "Courageous Sailing") or by dropping off cash at Courageous Sailing. Please include a copy of your invoice.



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.