Just Getting Started?

You’re in the right place! Most beginners choose to combine Basic Keelboat Complete (a two-weekend course) with a Full membership. This is the best way to learn the basics and then sail at Courageous as a member once you’re ready to sail on your own. All Basic Keelboat courses are taught in Rhodes 19’s and are suitable for most ages and abilities. The goal of the class is to get you on the water with a red flag rating to practice the skills you have learned.

Basic Keelboat Complete


Per Person
  • 4-day, 24-hour course
  • US Sailing certified course
  • Basic theory, sail trim, knots, and basic navigation
  • Everything You Need to Know to Be a Skipper
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Basic Keelboat Part 1


Per Person
  • 2-day, 12-hour course
  • Introduction to sailing
  • Rigging and unrigging, knots, sail trim, and steering
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Basic Keelboat Part 2


Per Person
  • 2-day, 12-hour course
  • Build on the basics
  • Get comfortable with sail trim, docking, and more
  • Essentials you need to start sailing
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More performance

The next step for sailors looking to increase their skills, Courageous offers advanced keelboat courses. Taught in J/80’s, a higher performance boat than the Rhodes 19, this course goes in-depth into sail trim, theory, docking and piloting on a larger and faster vessel.

Advanced Keelboat


Per Person
  • Two Day, 12 Hour Course
  • Advanced Sail Trim and Theory
  • Taught on a J80
View Course Details

Cruising Certification

Everything you need to get started on cruising! Our basic cruising class is taught on an Erikson 28 and will teach you everything you need to know to start cruising Boston Harbor and the Boston Harbor Islands. Start with the basics and then work your way up to becoming bareboat certified and ready to take on a week in a chartered cruising boat down south next winter.

Basic Cruising


Per Person
  • Four Days, 24 hours total
  • Docking, Mooring, and Anchoring
  • Boston Harbor Navigation
  • Comprehensive Introduction to Cruising
    View Course Details

    Bareboat Cruising


    Per Person
    • Four Day, Including Two Overnights
    • Advanced Cruising Techniques
    • Everything You Need to Know to Bareboat Charter
    View Course Details

    Course & Membership Package Deals

    Purchase a course and membership package to get ready for the upcoming season. Packages are available for certain courses and membership combinations and can save you hundreds of dollars off the full price.
    How to purchase: Find the combination you like and add both the course and the membership to your cart. The discount will automatically be applied to your subtotal during checkout.

    Group Practice

    On alternating Saturday and Sunday mornings, join other members and students looking for extra practice, coached by one of our senior instructors. This is a great way to hone the skills necessary to progress from Red Flag to Yellow Flag rating, get out on the water and work towards earning your Red Flag rating (if your instructor has given you specific skills to work on), gain more confidence at the tiller, or to get back into it if you haven’t been sailing in a while.

    Course dates have not yet been set for 2017. Signup for our newsletter to stay informed.

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