Fall in Love with Sailing!

In honor of the boat show being in town, we are bringing our specials straight to your door! 

While we won't be hosting a table at this years show, we welcome you to join us in welcoming in a new season with a flash sale on some of our most sought after courses. 

If you are looking for a unique gift to give this valentines day, or a new an fun reason to join us on the water this season, this is it!

Enjoy 10-50% off courses, membership, and Harbor Cruises. 

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Private Lessons & Harbor Cruises

The perfect gift for the 2022 season!

Whether you are purchasing for yourself or someone else, you can't go wrong with a 2-hour personalized experience on Boston Harbor.

Check out our 2-hour sail options!

Rhodes 19 Core Fleet

The Rhodes 19 is backbone of the Courageous fleet with 27 Stewart-made keelboats and counting. Stable and easy to handle, they offer a fun, comfortable sailing experience for sailors of all calibers, from novices to seasoned one-design racers.

Boat Show Sale- 10% OFF

Individual

$745
$671
  • One registered skipper
  • Access to 27 Rhodes 19s
  • One-year term
  • Includes unlimited guests

Boat Show Sale- 10% OFF

Family

$875
$788
  • Two registered skippers
  • Access to 27 Rhodes 19s
  • One-year term
  • Includes unlimited guests

 

Mid-Fleet Cruising

If fast, friendly, easy-to-sail boats and Harbor Island cruising are calling your name, this is the membership for you! The Mid-Fleet Cruising membership gives you access to our four J80s and a Tanzer.

Sells out quickly!

Individual

$999
  • One registered skipper
  • One-year term
  • Includes access to 4 J80s, a Tanzer, and 27 Rhodes 19s
  • Easy, fun boats to sail fast
  • Explore farther away from base
  • Boats available all week long

 

Sells out quickly!

Weekday

$799
  • One registered skipper
  • Weekdays only | One-year term
  • Includes access to 4 J80s, a Tanzer, and 27 Rhodes 19s Monday-Thursday and 27 Rhodes 19s all week long
  • Easy, fun boats to sail fast
  • Explore farther from base
  • Boats available Monday-Thursday

 

Cruising

For many, the Cruising Membership is the most coveted membership tier. The cruising fleet gets you out farther, faster, and for longer. Our 4 30'-35' boats have at least 2 berths and a head aboard, allowing you to cruise in comfort. Take a day trip to a harbor island or pick up a mooring for a night at sea. Memberships go quickly, so get yours before they are gone!

Almost Gone!

Individual

$2550
  • One registered skipper
  • One-year term
  • Includes access to 4 30'-35' Cruisers, 4 J80s, a Tanzer, and 27 Rhodes 19s
  • Comfortable larger boats with engines
  • Explore farther away from base
  • Boats available all week long

 

Limited Quantities Available!

Weekday

$1500
  • One registered skipper
  • Weekdays only | One-year term
  • Includes access to 4 Cruisers, 4 J80s and a Tanzer Monday-Thursday and 27 Rhodes 19s all week long
  • Comfortable, larger boats with engines
  • Explore farther away from base
  • Boats available Monday-Thursday

 

Learn to Sail

This is the best way to learn the basics! This course covers all you need to know to sail on your own at Courageous as a member. All Learn to Sail courses are taught in Rhodes 19s and are suitable for most ages and abilities.

Bundle & Save! Purchase our Learn to Sail 1 & 2 together and you'll save over $100. Add in a membership to save more than 50% on your membership price!

Boat Show Sale- 10% OFF

Learn to Sail - Part 1

$355
$320
  • 2-Day, 12-hour course
  • Introduction to sailing
  • Rigging, knots, basic boat handling
  • Follow up with Part 2 for the full curriculum

Boat Show Sale- 10% OFF

Learn to Sail - Part 2

$355
$320
  • 2-Day, 12-hour course
  • US Sailing Certification available
  • Build on the basics from Part 1
  • Build comfort with sail trim, docking, and more

 

Intermediate Sailing

Ready to get out on some larger boats? Or maybe sail a little faster? We have some great deals on courses that will introduce you to performance sailing.

Meet the J80 is our aptly named, one-day clinic that will help you either get comfortable on a different boat after learning to sail on our Rhodes 19s or show you how to introduce this sportboat to others. Also discounted for Black Friday, our Mid-Fleet Performance 1 course will give you a firm foundation in Performance Sailing as well as prepare you to take our Mid-Fleet Cruising checkout.

Boat Show Sale- 10% OFF

Performance 1

$325
$293
  • 2-Day, 12-hour course
  • Advanced sail trim and theory
  • Refined boat handling
  • Advanced techniques and maneuvers

 

Boat Show Sale- 10% OFF

Performance 2

$350
$315
  • 2-Day, 12-hour course
  • Rigging and sailing with the asymmetrical spinnaker
  • More advanced sail trim, theory, techniques, and maneuvers 

 

Boat Show Sale!- 10% OFF

Boston Harbor Navigation

$215
$194
  • 6 hours over a single weekend day or two weekday evenings
  • Practical, one-the-water guide to the outer harbor
  • Visual navigation practice
  • Great prep for the Green Flag test

 

Cruising Courses

Everything you need to sail bigger boats with confidence! All courses are taught on one of our cruising boats, ranging from 30' to 35'. Start with the basics-- we recommend the  First Mate course!--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.

A fan favorite, going fast!

First Mate

$225
  • 1-day, 6-hour course
  • No pre-requisites or sailing experience required
  • Learn how to support a skipper during standard maneuvers such as docking and crew-overboard
  • Learn basic terminology 
  • Introduction to points of sail, sail trim and rigging

 

Boat Show Sale- 10% OFF

Basic Cruising

$895
$806
  • 4 Day, 24-hour course
  • US Sailing certification available
  • Get started cruising around Boston Harbor
  • Practice docking, mooring, anchoring, and navigation underway.
  • Introduction to mechanical systems

 

Holiday Sale- 10% OFF

Bareboat Cruising

$1200
$1080
  • 4 Day, 40-hour course, including 3 days and 2 nights aboard
  • US Sailing certification available
  • Gain the knowledge and experience you need to bareboat charter or skipper a multi-day cruise on a Courageous boat (or your own!) with confidence
  • Take a deeper dive into mechanical systems & auxiliary power

 

Private Lessons, Cruises, and Additional Sailing Courses

Whether you're looking for an intimate date night far away from the crowds or a customized lesson to brush up on your skills, we've got you covered. Join us for 2 hours on the water in 2021, and we promise you'll leave stress and worry on the dock. 

Holiday Sale- 50% OFF

Private lessons 

starting at  $190
$95-150
  • 2 Hours of instruction
  • Flexible schedule
  • One on one with a qualified instructor
  • Available for all skill levels and boats

 

Boat Show Sale- 50% OFF

Boston Harbor Cruise

$190
$95
  • 2 Hours on the water
  • Great way to experience sailing
  • Bring up to 3 additional people
  • Take the helm or let your qualified skipper do the work while you take in the beauty of the Harbor

 

Boat Show Sale- 10% OFF

Night Sailing

$225
$203
  • 5-Hour, 1-evening lesson
  • Practical, on-the-water class
  • Learn what it takes to sail and navigate with confidence at night and in restricted visibility