Life is Better When You're Sailing

Sailing Lessons

For thousands of years man has been harnessing the power of wind. Mother nature’s breath of fresh air has moved cargo and people across oceans for millennia. 

Stuart Sailing can introduce you to this ancient art. A sailing lesson is one of true empowerment. Come on board the Sailfish as your classroom, or have us help you learn your own vessel!

Welcome aboard Sailfish, your classroom for Real World Sailing Lessons. 

This catamaran and captain allows for a unique opportunity to learn the basics of safely operating a catamaran! Our personalized syllabus is an ideal tool to help maximize your learning experience. 

With captain Matty as your instructor you will feel comfortable and confident sailing a 40 foot cruising cat. Sailfish’s stable platform and easy maneuverability is a breeze in light winds. 

Learn the basics of wind lift, apparent and true wind directions, tacking and gybing. We will also learn many aspects of overall boat safety, tying knots and boat mechanics.  

We will cover reefing sails when the wind “pipes up” as well as  “pinching up” and “falling off”. When complete you will have a better understanding of how and why a sailboat moves the way she does. Whether you are a new sailor or an old salt Capt. Matty will be at your side to assure you get the most out of your sailing lessons.

Aboard Sailfish learning is fun and rewarding, with private sailing lessons!

Sign up for Sailing School

Per Hour

Lessons are $195 per hour for individualized instruction.
$195hour
Sign up for school

3 Days of 4 hour classes

Tailored education for those wanting to gain confidence for future bareboat chartering.
$23003 days
Enroll in 3 day course

Overnight

For those looking to fast track from curious interest to solid experience.
$2100nightly
Book Boarding School

Clients Say

Ah-maz-ing, we had the best week! We had no idea how beyond perfect it would all be! The crew made it beyond our imagination!

Edie Watts

Edie Watts

The beauty of this company is its customization, this is not a cookie cutter experience.

Savitri Hook

Savitri Hook

Truly a life changing trip! I went on a Keys spearfish charter on the Sailboat. Erinn and Captain Matty made it the trip of a lifetime! Amazing food and well organized vessel! youtube.com/c/CaptainJackSpearo

Captain Jack Spearo

Captain Jack Spearo

I must say we enjoyed my daughters 17th birthday with 2 of the most respectable people. Captain Mattey and Skipper Erinn showed us mad love, I highly recommend them!

Stacey Stallworth

Stacey Stallworth

Our Crew

Skipper Erinn Hennessy
Skipper Erinn Hennessy
First Mate / Hostess
Erinn Hennessy 561-801-0080 ErinnLovesHealth.com
Captain Paul “Popeye” Jones

Paul has been sailing since 1979.  He owned a series of larger sailboats in the states and then owned a Moorings/Beneteau 432 charter boat based in Tortola British Virgin Islands for 8 years in the 1990’s. He traded time on it…

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