Private Rhodes 19 or J/22 Lesson or Cruise 

2-hour sail for up to 4 (Rhodes 19)

Regular Price: $95/ hr
Holiday Special Nov. 27 - Dec. 31: $95 for 2 hours - 50% off! 


2-hour sail for up to 4 (J/22)

Regular Price: $125/ hr
Holiday Special Nov. 27 - Dec. 31: $125 for 2 hours - 50% off!

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Courses can be scheduled beginning in January. Please retain your PayPal email confirmation to schedule your course. 


This two-hour lesson or cruise is an opportunity for up to 3-4 people to experience the fantastic views from Boston Harbor, learn some sailing skills, or just sit back and enjoy the ride on a comfortable, stable nineteen-foot keelboat. An expert instructor will be there every step of the way, and will be happy to customize the experience for you.

If you’d like a private lesson (beginner or more advanced), no problem--you’ll be amazed by how much you can learn in just two hours, even if it’s your first time on the water. Private lessons are a good choice if you're working towards a particular rating here at Courageous, would like one-on-one coaching for specific skills, need more scheduling flexibility than our group courses offer, or want to bring a group of mixed ages or experience levels.

If a leisurely cruise or harbor tour is more your style, great! Or combine a little bit of both for a fun, unique experience. Just let your instructor know what you’re looking for, and we’ll do our best to make it happen!

Feel free to bring a picnic or snacks for the sail (note that alcohol isn’t permitted before or during sailing). Life jackets are provided. Both Rhodes 19s and J22s fit up to 3 or 4, in addition to the instructor; choose the J22 option if you’d prefer a slightly larger, faster boat or would like a more advanced lesson. Please contact us directly if you'd like to book a private course, a sail on one of our cruising boats, or a lesson or sail lasting more than two hours.


Basic Keelboat Complete (24 Hours)

Prerequisites: None
Regular Price: $645
Holiday Special Nov. 27 - Dec. 31: $516 - 20% OFF!
Optional US Sailing Certification Fee: $75
Included Text: US Sailing Basic Keelboat

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Courses can be scheduled beginning in January. Please retain your PayPal email confirmation to schedule your course.  

When your goal is to become a competent, confident sailor with a solid understanding of the basics, this is the course to take.

At the end of the two-weekend class, most students are ready or almost ready to skipper one of our Rhodes 19 keelboats on their own.  Your instructor, who will always be in the boat with you and up to two fellow students, will guide you through the sailing fundamentals, combining short chalk talks and extensive on-the-water coaching to help you develop and reinforce new skills.  You’ll learn all you need to know to rig and unrig your boat, leave and return to the dock safely, adjust your sails and rudder to make the boat go where you want it to go, and tie some important knots (always a good way to impress your non-sailing friends!).

It’s a lot of work, but by the completion of the course, most students are ready for a Red or Yellow Flag skipper rating , which means they can safely skipper a small keelboat in light to moderate conditions without an instructor. Students who earn a Yellow Flag rating can also take a written test to obtain their US Sailing Basic Keelboat certification, a standard recognized throughout the U.S. and in many other parts of the world.

Basic Keelboat Complete courses take place over two consecutive weekends, Saturday/Sunday/Saturday/Sunday from 10-4:30 each day, with a half hour hour lunch break.  A new course starts almost every Saturday.

If you'd like to keep sailing as a Courageous member after your course (and who wouldn't?!) check out our Course and Membership Combos for great discounts.

Below is an overview of the knowledge you will gain:

Practical Skills

  • How to use weather forecasts to evaluate sailing conditions
  • How to board a sailboat, do a safety check, and prepare to sail
  • How to rig, derig, and secure the boat to the dock
  • How to safely leave and return to the dock
  • How to safely maneuver the boat: starting, stopping, controlling speed, steering, tacking, jibing, getting out of irons, etc.
  • How to handle control lines and trim sails
  • How to depower sails if the wind picks up
  • How to safely recover a crew overboard
  • How to read a nautical chart of Boston Harbor
  • How to apply the Rules of the Road
  • How to recognize and navigate around Aids to Navigation 


  • Sailing nomenclature
  • Basic sailing theory
  • Points of sail
  • Basic Navigation Rules
You can see the whole US SAILING Basic Keelboat curriculum here.

US Powerboating Safe Powerboat Handling

Prerequisite: None
Regular Price: $145
Holiday Special Nov. 27 - Dec. 31: $116 - 20% OFF!
Suggested Age: 12 - adult
Certification(s) Earned: NASBLA certificate, MA boating education certificate, Safe Powerboat Handling certificate.
US Coast Guard & NASBLA Approved
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Courses can be scheduled in early January. Retain the your PayPal email confirmation to schedule your course. 


This 16-hour hands-on, on-the-water course is for anyone who wants to learn how to safely operate a small motorboat and improve their boathandling skills on actual boats.

The US Coast Guard and the National Association of State Boating Law Administrators (NASBLA) have approved this course and an increasing number of states have recognized it as meeting their requirements for a state boating safety education certificate. These national and state approvals call for the course to include a total of six to eight hours of classroom sessions covering required education topics. Students learn:

On-the-Water Sessions

  • Engine & electrical systems
  • Starting procedures
  • Docking
  • Leaving & returning to a slip
  • Close-quarters maneuvers
  • Anchoring
  • Steering a range
  • Proceeding to a destination
  • Person in Water rescue

Classroom Sessions

  • Safety, prep & weather
  • Maneuvering concepts
  • Registration & capacities
  • Equipment requirements
  • Prep & fueling procedures
  • Navigation rules of the road
  • Aids to navigation
  • Environment regulations


Courageous Sailing

A great Place for Sailing and SailBlind

SailBlind's involvement with Courageous Sailing Center (then Pleasure Bay) began in the late 1970's and early 1980's.  At that time, we weren't even called Sailblind, and Courageous Sailing Center had yet to develop with the docking of the 12-meter namesake at the present site. Harry McDonough was running Pleasure Bay, and we got a chance to sail on boats called Brutal Beasts, a cat boat with only a mainsail, no jib. Compared to our program of today, we had no "competitive branch" nor did we have all the techniques that we use today.  Instead, Arthur O'Neill and a few of us adventurous folks would get to Pleasure Bay and sail for a few hours under Harry's tutelage.  Occasionally, he'd come out in his little motorboat and "coach" us, admonishing us to steer straight and "for chrissake let the sail out!"

Then, sometime in the 1980's, we moved to the present site in Charlestown, Courageous Sailing. While sailing at the current facility, we became aware of the first World Blind Sailing Championship to be held in Auckland, New Zealand in 1992. It was at this point that CSC was instrumental in providing the boats and expertise so necessary to help in forging a competitive blind sailing team. At this point, the name SailBlind was born, and we have gone by that team name ever since.

Our association with CSC didn't end after the first World Blind Sailing Championship. In fact it developed even further, to the point where they host our Wednesday night practices (for the competitive sailors) and the recreational sailing program on Saturdays from June to early September. Additionally, they have hosted many regattas for blind sailing.

On a personal level, I have benefitted greatly from sailing at CSC, both as a competitive sailor practicing on Wednesday nights, and as an occasional participant in evening races. Dave and his crew have always been helpful to us by working with us to schedule practices and getting us into some of the Courageous weekly races. Of particular importance is that they were there for us prior to any of our major competitive events, particularly the World Blind Sailing Championships. By providing us with practice times and access to their boats, we were able to train prior to these events, even during some of the winter months.

Finally, I'd like to take this opportunity to thank CSC for supporting us, both as individual sailors and as a team. Your support of SailBlind certainly played a role in many of our teams medaling in the World Blind Sailing Championships over the years. Without your help, our achievements would have been made more difficult, if not impossible to attain.  May we have many more years working together.  Thanks, CSC for all you do in supporting us.

Matthew Chao

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