Welcome to Barefoot Offshore Sailing School!
Celebrating 20 years of teaching sailing schools in the Grenadines!

Our weeklong, live-aboard ASA Sailing Courses give students hands-on experience while exploring the lovely islands of the Grenadines. We offer beginner, advanced and catamaran courses that teach you what you need to know to charter your own yacht anywhere in the world. We run the cruises every week of the year on catamarans and monohulls between 38 and 50 feet.

After more than 20 years as an ASA sailing school, we continue to develop and improve our standards and service and enjoy an unusually high percentage of returning customers – some of whom have now bought yachts and placed them in our fleet.

Barefoot Offshore Sailing School operates in one of the most beautiful cruising grounds in the world, St Vincent & The Grenadines.  The sailing ground is as attractive to well-seasoned sailors as it is to complete novices.

In response to requests from the many Canadians that participate in BOSS courses, BOSS has entered into an agreement with Wavelength Sailing School of Kingston Ontario to offer Learn-to-Cruise courses leading to awarding of Sail Canada certifications.

Several highly qualified Sail Canada instructors have been recruited to participate in this unique initiative.

Testimonials from some of our Barefoot Offshore Sailing Schools

“Mr. Pratley, Thank you for reaching out to me. I would very much agree that I received a great deal of value for my dollar in terms of my experience with Barefoot Charters. My interactions with the staff and instructors were pleasant, and I feel very comfortable recommending Barefoot to my family and friends.

I especially am appreciative of my instructor, Rob; he was an outstanding teacher and consistently demonstrated professionalism and competence during our entire course. After spending a week under his tutelage, I feel much more confident in my abilities as a sailor to safely operate a boat.
Thank you again for reaching out, and I hope to visit again in the future!”

I think this course was definitely good value because it was one of the cheapest in the Caribbean.  I understand why the boat was almost 20 years old…it kind of had to be for the price you charge.  Overall I think it was a good course, and a good location to do it in.  Thanks

“Finn was absolutely fantastic. He balanced training for our skill set and brought together 5 crew/strangers and was able to train us all for our very specific needs and skill sets. Heals left us with a need to do more. I have had many training classes, Finn was by far the best trainer I have ever had.”

“I would like to commend you for running an excellent school with top-notch instructor Richie Britton.  Jeannie and I have different learning styles and Richie was perfect at working through both styles.  He made a tremendous impact to our learning experiences” – Beneteau 463,

We are great at what we do

Barefoot Offshore Sailing School is the longest-established sailing school in the Windward Islands and has operated for more than 20 years.   It’s also the most active ASA (American Sailing Association) sailing school in this part of the world.

We’re pretty experienced (our parent company, Barefoot Yacht Charters, has been here for nearly 35 years), and we operate in one of the most beautiful cruising grounds in the world, St Vincent & The Grenadines.  The sailing ground is as attractive to well-seasoned sailors as it is to complete novices.

Our Instructors are chosen not only for their professional sailing skills, but also because they’re folks who are good company and can get on with folks of all ages and from all walks of life.

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Custom BOSS Courses

  • Emergency Navigation

    Coming in September 2021, BOSS is introducing an Emergency Navigation course to be conducted in conjunction with Advanced and Offshore courses.  Additional details will be announced shortly.

  • B.O.S.S Diesel Engine Course

    Through this intensive 2 hour training course, participants will gain essential knowledge into the workings of a diesel engines and most common issues and solutions. You will learn how to properly take care of their diesel engine with safety as the priority. Upon completion, you will be able to diagnose and problem solve the most common issues that occur while out on charter, giving peace of mind while out on the water. True freedom comes when we know we can deal with all aspects of our vessel and in a safe and proper manner. BOSS’s Diesel Engine course provides this freedom.

  • B.O.S.S Rig Tune Course

    Through this course participants will learn how to correctly tune the rig on a yacht, assuring that your mast is set up safely and correctly for the sailing conditions you are going to experience. This course will not only teach you how to tune the rig, it will also teach how to identify any issues or problems with the rig prior to heading out and how to correct them.

“Mr. Pratley, Thank you for reaching out to me. I would very much agree that I received a great deal of value for my dollar in terms of my experience with Barefoot Charters. My interactions with the staff and instructors were pleasant, and I feel very comfortable recommending Barefoot to my family and friends.

I especially am appreciative of my instructor, Rob; he was an outstanding teacher and consistently demonstrated professionalism and competence during our entire course. After spending a week under his tutelage, I feel much more confident in my abilities as a sailor to safely operate a boat.
Thank you again for reaching out, and I hope to visit again in the future!”

“I would like to commend you for running an excellent school with top-notch instructor Richie Britton.  Jeannie and I have different learning styles and Richie was perfect at working through both styles.  He made a tremendous impact to our learning experiences” – Beneteau 463,

“Finn was absolutely fantastic. He balanced training for our skill set and brought together 5 crew/strangers and was able to train us all for our very specific needs and skill sets. Heals left us with a need to do more. I have had many training classes, Finn was by far the best trainer I have ever had.”

“Fabulous week – great fun on the sea, discovering islands, whilst learning to sail with great company!  Highly recommended!  Many thanks to the team!” – Michael Depping, Monohull

“Joel was great, perfect to learn from. His instruction is clear and helpful.”

“The value of the course and learning was amazing and far better quality than expected. Finn’s experience and way of sharing made the course what it was.”

“The Instructor rocked!  The course was fantastic.  We had enough time both for fun and learning” – Robert & Lindsay Hall, Catamaran, 

“Joel was fabulous a great instructor.”