Regular Price: Daysailing 24: $1150. Cruising 24: $1300. Cruising 30: $1900. Cruising 34: $2200.

Purchase before January 1 and recieve 2014 prices! Daysailing 24 is $1050 and Cruising 30 is $1800.

Daysailing 24


Cruising 24


Cruising 30


Cruising 34


For some of us, it's all about the big boats, backup engines, and thoughts of sailing around the world. Our cruising fleet won't take you quite that far, but it will take you out of the harbor and then some. Whether you want to invite friends and family for trips around the Harbor Islands, anchor for a picnic lunch, spend a night moored or at anchor under the stars, or practice your big boat skills in preparation for a bareboat trip in the Caribbean, we've got a convenient cruising membership option for you.

The Courageous cruising fleet is growing and improving every year, with boats ranging from 24 to 34 feet, including three J24s, an O'Day 240, a Tartan 27 yawl, an Erikson 28, a CS 30, and a Pierson 34. We offer four classes of cruising memberships. Our Daysailing 24 entry level option provides access to the J24s and O'Day 240 for day trips. The next level up (Cruising 24) includes overnights on the same fleet. Cruising 30 members may take the 27-30 footers for day trips and overnights; Cruising 34 membership includes the Pierson 34 as well.

Cruising membership also includes access to our fleet of twenty seven Rhodes 19s and nine J22s. All cruising members will need to have a check-out and orientation for the boats they will be sailing; please see our Flag Ratings section, especially "Green Flag for Cruising Members," for more information.

We carefully limit our available cruising memberships to ensure that everyone has plenty of access. To learn more about pricing and availability, please email Jake Denney, our Adult Program Director, at

Basic Cruising (24 hours)

Black Friday-Cyber Monday: 20% OFF!

Prerequisite: Basic Keelboat Complete or Basic Keelboat Parts 1 & 2 or equivalent experience. Participants must be comfortable and confident skippering and crewing on small keelboats.
Regular Price: $650
Optional US Sailing Certification Fee: $75
Included Text: US Sailing Basic Cruising
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Are you planning on purchasing your own cruising sailboat (or simply sailing ours!) or chartering in the Caribbean someday?  Our US Sailing Basic Cruising certification course is the first step for those who dream of going beyond Boston Harbor.  In this course, we apply the fundamentals to bigger boats (up to 30’ in length) with outboard gasoline or inboard diesel engines, and introduce the tools needed to sail longer distances.  While big boats sail just like small boats, there are more systems to learn and techniques to master.  Twenty-four hours is not enough to prepare students for every challenge a cruising boat can present, but it is enough to develop comfort around big boat basics, so that you can crew competently or take the helm under the supervision of a more experienced captain.  Basic Cruising takes place over two consecutive weekends, Saturday/Sunday/Saturday/Sunday from 10-4:30 each day, with a half hour hour lunch break.  Maximum of 4 students.

Graduates may test for their US Sailing Basic Cruising certification. The additional experience will also typically help boost the Courageous skipper rating of students with solid Rhodes boathandling skills, enabling access to the outer harbor and Harbor Islands.

You can see the whole US Sailing Basic Cruising curriculum here.

Bareboat Cruising (40 hours)

Black Friday-Cyber Monday: 20% OFF!

Prerequisite: Basic Cruising or equivalent experience. Participants must be experienced in basic navigation and maneuvering cruising boats (24+ feet) under sail and power.
Regular Price: $850
US Sailing Certification Fee: $75
Included Text: US Sailing Bareboat Cruising
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Once you start sailing the bigger boats, it’s hard to stop! And there’s always more to learn. Our Bareboat Cruising course is the next step. It picks up where Basic Cruising leaves off and covers topics such as navigation, anchoring, and heavy weather sailing in much greater detail. You’ll learn the things you need to know when chartering a sailboat: the various techniques used around the world for mooring and anchoring (e.g. stern and bow, fork, Mediterranean, Bahamian); controlling the boat under power with confidence; big boat docking techniques; provisioning; visiting the fuel and pump-out dock; VHF communication; and more. We will also take you through a tour of all the important boat systems, peering behind seat covers and into the bilge until you know exactly where everything is, what it does, and what to do (or who to call!) when it doesn’t work.  This course typically includes 3 days of sailing, two overnights at anchor or moored, and additional prep and debrief time.  Maximum of 4 students.

Upon passing the exam at the end of the course, your US SAILING Bareboat Cruising certification will signify that you have sufficient skills and knowledge to safely and confidently skipper an auxiliary powered cruising sailboat between 30’ and 45’ in length, in winds above 15 knots, within sight of land during daylight hours. This certification is widely respected and accepted by many sailboat charter companies in the US and other parts of the world.  Most Bareboat graduates are also qualified for a Courageous cruising membership.


Advanced Keelboat (12 hours)

Prerequisites: Basic Keelboat Complete or Basic Keelboat Parts 1 & 2 or equivalent experience
Regular Price: $295
Black Friday-Cyber Monday: 15% OFF!
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Whether your goal is to sail fast around a race course or to achieve the perfect spinnaker run home from The Graves, Advanced Keelboat is the course for you.  This course is taught in a J/22, a performance boat designed for speed and grace, by our top instructors.  If you are working on a Green Flag rating, preparing for a J/22 checkout, or are interested in getting into racing, Advanced Keelboat can help you work toward your goals- just let your instructor know what you'd like to focus on.

Advanced Keelboat covers: 

  • The finer points of boat handling: how to use crew weight to your advantage, reduce rudder drag, roll tack and jibe, etc.
  • Advanced sail trim: how and when to use the vang, outhaul, Cunningham, traveler, backstay, and other sail controls to determine the shape and maximize the performance of your sails.
  • All you need to know to use a spinnaker well: rigging, sets, jibes, douses, and proper trim.
  • A review of the basics and more advanced techniques, including docking, anchoring, crew overboard recovery, and heavy weather sailing.

Basic Keelboat Part 1 (12 hours)

Prerequisite: None
Included text: US SAILING Basic Keelboat
Regular Price: $295
Black Friday-Cyber Monday: 15% OFF!
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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: $295
Black Friday-Cyber Monday: 15% OFF!
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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.

Regular Price: $645

Black Friday-Cyber Monday: 25% OFF

Our individual Full membership gives you access to our whole Rhodes 19 fleet (27 boats!), 7 days a week, May 1st through October 31st (or for one calendar year if purchased after May 1st). It is by far the best value on the harbor. For an additional $100, get the J22 upgrade and use our more high performance J22 fleet as well. Don't forget a Guest Pass so that you can take your friends and family sailing!

Members must pass an on-the-water checkout and written test in order to sail a Courageous boat without an instructor; please see our Flag Ratings section for more information. Our sailing area extends out around the Harbor Islands for qualified members. Courageous is open noon - sunset on weekdays and 10 - sunset on weekends and holidays, May 1 through October 31. Boat availability is usually plentiful (with the exception of before 3:30 on weekdays during our 6-week summer Youth Program), but is not guaranteed.

Purchase your membership now by clicking on the Purchase Memberships tab to the left!

Private Rhodes 19 or J/22 Lesson

Private lessons are perfect if you prefer to learn one-on-one, need more scheduling flexibility than our group classes offer, want to troubleshoot specific skills to earn a rating, or would like to bring a group of mixed ages or experience levels.  We also offer private lessons for children and teens, individually or in groups of up to 4.  Let us know what you’re looking for, and we’ll do our best to make it happen!  Both Rhodes 19s and J/22s fit up to 3 or 4 students, along with the instructor.  Minimum of 2 hours per lesson; price includes up to 4 students.

Rhodes 19: $95/ hr (Minimum of 2 hours per lesson; price includes up to 3-4 students.)
J/22: $125/ hr (Minimum of 2 hours per lesson; price includes up to 4 students.)
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Private Cruising Lesson

Want some coaching on how a cruising boat handles?  If you’d like the chance to get comfortable with one of our cruising boats before taking out the boat on your own or get some pointers in preparation for a charter of your own, take a private lesson with one of our most experienced instructors.  Lessons can be taught on our Seafarer 30, Erickson 28, Tartan 27, O'Day 240, or J/24, all of which fit from 4 to 5 students.

Cruising Boat: $150/ hr (Minimum of 2 hours per lesson; price includes up to 5 students depending on the vessel.)
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Basic Keelboat Complete (24 Hours)

Black Friday-Cyber Monday: 20% OFF!

Prerequisite: None
Regular Price: $550
Optional US SAILING Certification Fee: $75
Included text: US Sailing Basic Keelboat
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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.

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

US Powerboating Safe Powerboat Handling

Prerequisite: None
Course Fee: $145 $116 - Holiday Special!
Suggested Age: 12–adult
Certification(s) Earned: NASBLA certificate, MA boating education certificate, Safe Powerboat Handling certificate.

US Coast Guard & NASBLA Approved

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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