Courageous offers a number of discounted membership and lesson combinations to encourage those who know they want to jump right in! Learn (or review) the basics with a course, and then put your new skills to good use with a one-month or one-year membership. For many, the Basic Keelboat Complete plus One Year Individual (Full) Membership combo is the perfect way to get started.

For combinations purchased during the sailing season (May 1 - October 31), your membership will begin when you finish your course, and run for either one calendar year or one month from the date you activate, depending on the membership you choose. Memberships expire October 31 if the combination is purchased before May 1. Please note that taking Basic Keelboat Part 1 only will not prepare you to sail on your own as a member.

Our combination packages are listed below. Please refer to the course and membership pages for descriptions of the various courses and memberships.

  • Basic Keelboat (Part 1 or Part 2) & One Month Membership $425
  • Basic Keelboat (Part 1 or Part 2) & One Year Individual (Full) Membership $725
  • Basic Keelboat Complete & One Month Membership $745
  • Basic Keelboat Complete & One Year Individual (Full) Membership $945

Course & Membership Combos can be purchased in person or over the phone, by calling 617-242-3821. We apologize we are not able to offer these online at this time. 

Group Practice Class

3 Hours

Group Practice Classes are a great way to practice some of the skills you learned in your Basic Keelboat Part 1 course, to gain some confidence before heading out on your own, or to brush up on skills if you're just coming back to sailing after a break. On alternating Saturday and Sunday mornings one of our senior instructors will lead on-the-water review sessions for up to 4 people or 2 boats. The morning will start with some on-shore chalk-talk, so come prepared with questions and then be ready to practice!  Students will be paired up to sail together in Daysailorss (unless you really want to practice single-handing with some supervision!) while the instructor coaches from a motorboat.  Some time each day will focus on specific skills, like docking or crew-overboard recovery techniques, or group practice drills to improve general boathandling. This is a great way to build from Red Flag to Yellow Flag, build more confidence, or to get back into it if you haven't been sailing in a while.
Prerequisite: Some sailing experience required
For more information about courses, or to purchase and schedule a course, please email Mike Kostigen, Jamaica Pond Site Director - Adult Programs, or call the JP Boathouse directly at 617-522-5061



Private Lessons and Charters

Jamaica Pond Daysailor - Up to 3 guests

Sailing made to order. For beginning to advanced sailors, on any topic.  Ask Mike and she will put together a lesson, course or cruise just for you!
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

Basic Keelboat Part 1 (12 hours)

Prerequisite: None
Included text: US SAILING Basic Keelboat
Regular Price: $325
Boat Show Special: 10% OFF!
book now    book now    book now

Our Basic Keelboat Part 1 course covers the fundamentals of sailing.  We’ll teach you how to rig and unrig the boat, leave and return to the dock safely with a bit of guidance, and adjust your sails and rudder to make the boat go where you want it to go.  This is the first half of the complete course, and perfect if you just want to try out sailing without committing to a 24-hour course, you prefer a more relaxed pace, or your schedule can’t accommodate two consecutive weekends.  Basic Keelboat Part 1 tends to follow a consecutive Saturday/Saturday or Sunday/Sunday schedule, from 10-4:30 each day, with a half hour hour lunch break, but can also be taken in one weekend (Saturday and Sunday) or in 3-hour intervals on weekday evenings.

In twelve hours, you’ll learn enough to get you off to a good start, and you’ll probably find that you can sail with confidence with just a little bit of help from an instructor.  Please refer to the Basic Keelboat Complete description for more information.

Basic Keelboat Part 2 (12 hours)

Prerequisite: Basic Keelboat Part 1 or equivalent experience
Included text: US SAILING Basic Keelboat
Regular Price: $345
Boat Show Special: 10% OFF!
book now    book now    book now

This course picks up where Part 1 left off. It is the next step for those who already know some of the basics, or for Part 1 graduates who are ready for more.  In Part 2, we review the basics like tacking and jibing, and continue with the rest of the Basic Keelboat Complete curriculum, including docking under sail, crew overboard recovery techniques, and refining your boat handling skills.  Basic Keelboat Part 2 tends to follow a consecutive Saturday/Saturday or Sunday/Sunday schedule, from 10-4:30 each day, with a half hour hour lunch break, but can also be taken in one weekend (Saturday and Sunday) or in 3-hour intervals on weekday evenings.

By the end of the twelve hours, you arrive at the same place as those who take the 24-hour complete course, eligible for a Courageous skipper rating (which means you can sail without an instructor!) and US Sailing Basic Keelboat certification.

Saturday, 26 January 2013 12:40

Boston Family Boat Buiding

Written by
Boston Family Boat Building's Boat Launch


High School Racing Teams

The British School sailing team trains at Jamaica Pond.

For more information about high school sailing, please email Mike Kostigen, Jamaica Pond Site Director or call the JP Boathouse directly at 617-522-5061

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. At Jamaica Pond, past school partners include the Curley School and the J.P. Manning School.

For more information about high school sailing, please email Mike Kostigen, Jamaica Pond Site Director or call the JP Boathouse directly at 617-522-5061
Age 11 and up
Limits Open to Boston Public Schools
Location Jamaica Pond

After School Sailing

This program is open to students who have sailed with us 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 only offered at the Jamaica Pond site.
Age 11 and up
Limits Step 3 and above
Location Jamaica Pond
Wednesday, 09 January 2013 19:00

Day 6 Recap

Our first day of frostbite racing in the new year was a great one -  24 boats on the line, sunshine, brisk but not bone-chilling, and 6 races completed despite two postponements!  The breeze was heavier than expected, gusting over 20 knots at times.  Without reefs in, the R-19's were screaming around the racecourse.  Saturday's conditions were on the edge of [Courageous Sailing's] reefing territory, so the Rhodes were about as loaded up as we'll let them get before shortening sail. Results will show Mark Lindsay and Jim Watson handily taking first for the day with 11 points, followed by Bryan Lee and Rob Breslin (26 pts), Chris Palmieri (28 pts), and Marston Brand at 31.2 pts.  
This coming Saturday is forecast to be mid to high 40's, cloudy, and light at 5 kts S.  Be prepared to obsess over the being on the line with speed at go and having perfect light-wind keelboat tacks.
>Here's a quick article on tacking keelboats.  
Heres a video of a Thistle doing a sweet roll tack, and by video I mean a set of slides with a ridiculous soundtrack - but the Boomshakalaka crew does a masterful job of snapping their boat through a tack.  The three crew members are impressively synced up.
Internal view of thistle tacking.
Here is a Melges 20 gently finessing their hull through some light breeze, with the utmost attention paid to crew weight in the boat.  The team delicately transfers their weight, fully aware that the smallest roll to windward at the wrong moment could kill their momentum.
In each of these clips, check out the skipper's tiller position through each point of the tack.  Watch it over and over and over again.  Then practice using two chairs and baseball bat.  Then come down on Saturday and practice in the boat on the way out to the course.  We'll try to get some video of tacks and throw the clips online.  
Last week Albert brought some very tasty vegetarian chili.  Unfortunately our meat chili suffered a mishap, so we were low on food.  Please sign up for this coming weekend!
We need:
2 judges
bowls (perhaps something like this to help prevent spillage?)
bread / rolls
sour cream
Veg Chilli 
  (Or whatever you feel like making/buying/bringing!)
As always, please give a heads up in advance you won't be able to make it and do not have anyone to fill in, or if you need a crew/skipper.  
-- Cha

2015 Summer Youth Program Lottery


Lottery Registration Opens March 1
Lottery Registration Closes March 15
Confirmation Letters Mailed March 27


Registration in 2015 will be lottery-based. There is NO advantage to submitting a registration form early. This is NOT a "first-come-first-served" system. Forms must be completed online (link below). More Rules and Restrictions


How to Register for the Lottery:

  1. Choose the Step that's right for you based on your age and experience. Read class descriptions.
  2. Choose your preferred session dates and locations (up to four, in order of preference).
  3. Complete and submit the online registration form by March 15th, 2015.


Click to go to the online registration form >



Confirmation letters regarding registration and waitlist status will be mailed to registrants no later than March 27, 2015. Please allow one week from that date (until April 3) for delivery prior to calling the office. Thank You!


Rules and Restrictions

  • All Courageous Sailing Youth Program students registering for classes in Step 1, 2, 3 or 4 MUST provide proof of their ability to swim at least 25 yards and tread water for 90 seconds. All students in Step 3 and above will be subjected to an on-site "swim check" by Courageous instructors. Download Swim Test Form. Note that the swim requirement does not apply to "Swim, Sail, Science" students or "Summer Learning Project" students.
  • Before registering for the lottery, please note the age and skill requirements for each Step.
  • All students entering the lottery for Jamaica Pond classes MUST prove their Boston residency per order of the Boston Parks and Recreation Department. Proof of residency requirements will be posted closer to the registration period.
  • Lottery registration forms must be submitted by Sunday, March 15, 2015. The online form will not be available after March 15, 2015.
  • All lottery registration forms received will be processed in the following order of priority: (1) returning students, (2) siblings of returning students, and finally (3) new students who have no siblings in the program.
  • Waitlists are capped at 40. All students whose lottery registration forms have been processed will received confirmation fo their status of registered, waitlisted, or not registered.
  • Post-lottery: Once you receive a letter of confirmation, you may make changes, additions or cancellations via telephone, subject to availability. Please email or call the office 617-242-3821 as soon as possible if you must cancel your class. Be advised that "no-shows" will not be admitted but will instead be automatically waitlisted should they choose to apply for the 2015 program.
  • We expect long waitlists due to the high demand for our programs and very limited number of spots. Thank you for your patience and understanding.