Adult Program Employment Opportunities


At Courageous we are committed to making the highest quality sailing education accessible to the community. We rely on instructors who are both great sailors and great teachers. If you have taught sailing before, or have wanted to, we want to hear from you!
 
Adult Program Instructor positions are typically part-time, with most classes running on the weekends and weekday evenings, so are often a great fit for those with "real jobs" who want to do something totally different in their spare time.  Some full time instructor positions are also available.

Boat Donations/Sales

Donated boats are typically used in our youth and membership programs and then sold after several years of use to help keep our youth sailing programs FREE.  In particular, we are looking for good quality Rhodes 19s, J/22s and larger cruising boats.  Please contact Fleet Manager Dan Keenan via email if you are considering donating a boat to Courageous.

Our inventory of boats for sale is changing all of the time.  For an updated listing of what Courageous has for sale please email Dan Keenan.

List of Boats Currently Available:

"Midnight Special" 1974 Ranger 23  ($2,000) [UNDER OFFER 11/23/11]

"Small Change" 1976 Ranger 23  ($2,000) [AVAILABLE 11/23/11]

"Clara Lee" 1970 Westerly Cirrus  ($3,000) [UNDER OFFER 11/23/11]

 

In Boston for a day?

Come to Courageous Sailing! You can go sailing on your own or let one of our expert skippers take the helm and discover Boston from the water. Whether your ideal outing is a family trip, a Corporate Sailing Event or the thrill of competing in a regatta, we have the best option for you!

We are just a few minutes away from Downtown Boston.

Call us now to schedule your outing! Contact Dave DiLorenzo or Cha O'Connell at 617-242-3821 or by email: dave@courageoussailing.org and/or cha@courageoussailing.org.

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Group Practice Classes (3 Hours)

Price: $30, $25 for members

Click Book Now to buy AND schedule your course! Click Buy Now to purchase, but schedule at a later date. To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.

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On alternating Saturday and Sunday mornings, join other members and students looking for extra practice, coached one of our senior instructors. This is a great way to build from Red Flag to Yellow Flag, earn your Red Flag (if your instructor has given you specific skills to work on), gain more confidence, or to get back into it if you haven't been sailing in a while.  The class starts with an on-shore chalk talk on topics requested by participants, so come prepared with questions.  Students will be paired up to sail together in Rhodes 19s (unless you really want to practice single-handing with some supervision!), while the instructor coaches from a motorboat.  The class might focus on particular skills, like docking or crew-overboard recovery techniques, or on drills to improve general boat handling--let the instructor know what you’d like to work on.  Maximum of 12 participants.

Private Lesson

Prerequisite: None
Rhodes 19: $95/hour; 2 hour minimum  
J/22: $125/hour; 2 hour minimum
Cruising Boat: $150/ hour; 2 hour minimum
 
Courageous members receive a 50% discount on all private lessons. 
 
To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.
 

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You’ll be amazed by how much you can learn in just a few hours! Let us know what you'd like to focus on, and we can tailor a lesson or series of lessons for you at any level. Lessons are most effective for 1-3 participants, and total beginners are welcome. Private lessons are a good choice if you're working towards a particular rating here at Courageous, prefer one-on-one coaching, need more scheduling flexibility than our group courses offer, or want to bring a group of mixed ages or experience levels. Most lessons are taught on a Rhodes 19; if you'd like to sail on the slightly larger, higher performance J/22, please contact us directly to buy or schedule your lesson.

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!


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 Erickson 28, CS 30, Pearson 34, Tartan 27, O'Day 240, or J/24, all of which fit from 4 to 5 students.

To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.
 

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Advanced Keelboat (12 hours)

Prerequisites: Basic Keelboat Complete or Basic Keelboat Parts 1 & 2 or equivalent experience
Regular Price: $345
 
To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.
 

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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 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. Our 3:1 student to instructor ratio ensures that we'll be able to tailor the course to the interests of you and your fellow students.

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 symmetrical 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.

 

Bareboat Cruising (40 hours)

Prerequisite: Basic Cruising or equivalent experience. Participants must be experienced in basic navigation and maneuvering cruising boats (24+ feet) under sail and power. Green Flag rating recommended for Courageous members.
Optional US Sailing Certification Fee: $75
Included Text: US Sailing Bareboat Cruising
Regular Price: $895
 
To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.
 

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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.

Many course participants choose to test for their US SAILING Bareboat Cruising certification, which signifies 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.

Passing this course qualifies the student to apply for their International Proficiency Certificate. This is needed if they wish to bareboat cruise in the European Union (EU).

 

Basic Cruising (24 hours)

Prerequisites: Basic Keelboat Complete or Basic Keelboat Parts 1 & 2 or equivalent experience. Participants must be comfortable and confident skippering and crewing on small keelboats; Courageous members must have a Yellow Flag rating or higher.
Optional US Sailing Certification Fee: $75
Included Text: US Sailing Basic Cruising
Regular Price: $695
 
To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.
 

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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, cover the basics of navigation, 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. Although 24 hours isn't enough to prepare you for every challenge a cruising boat can present, you'll have plenty of time to get to know the outer harbor and develop comfort around big boat basics so 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. This course will also cover what you need to know to pass the theoretical portion of the Green Flag test, which (along with an on-the-water checkout) enables access to the outer harbor.

Here's a brief overview of what you'll learn in Basic Cruising:

  • Rigging, derigging, and securing boat to dock
  • Docking and leaving the dock under power
  • Diesel and outboard basics
  • Maneuvering under sail
  • Maneuvering under power
  • Crew overboard recovery
  • Anchoring and mooring
  • Reefing and using the roller furler to shorten sail
  • Winch use
  • Chart reading and course plotting
  • Navigation: compass use, establishing a 2-3 point fix, using danger bearings, identifying aids to navigation, GPS use and navigation apps
  • Building familiarity with outer harbor destinations, hazards, safe docking locations, and favorite routes
  • VHF use

 

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

Basic Keelboat Complete (24 Hours)

Prerequisite: None
Optional US Sailing Certification Fee: $75
Included text: US SAILING Basic Keelboat
 Price: $645
 
 
To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.
 

book now    book now    

If 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, understand the basics of how sailing works, and tie some important knots (always a good way to impress your non-sailing friends!).

By the end of this challenging, hands-on 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.

Here's an overview of what you'll learn in Basic Keelboat Complete:

Practical Skills

  • How to use weather forecasts to evaluate sailing conditions
  • How to board a sailboat, do an equipment 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 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 recover a crew overboard
  • How to tie the knots you'll need
  • How to read a nautical chart of Boston Harbor (intro level)
  • How to apply the right of way rules
  • How to recognize and navigate around aids to navigation

Knowledge

  • Sailing terminology
  • Basic sailing theory
  • Points of sail
  • Right of way rules
 

Basic Keelboat Part 1

12 hours

Whether you're totally new to sailing or haven't sailed in a while, our BK Part 1 course is a great way to give sailing a try without a big commitment! If you like it, come back for BK Part 2 (in our Charlestown Boston Harbor site) and work towards your US Sailing Basic Keelboat Certification.
Prerequisite: None
Included text: US SAILING Basic Keelboat.
 
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