• DECEMBER 1-7 ASA 101-104 ONLY $1,799!


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  • “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....Finn was by far the best trainer I have ever had.”

    F Hartnett – Feb 2018

  • “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.”

    Bob – Feb 2018

  • "If you really wish to learn how to sail, this is hands down, the best place on the planet! We did out courses almost 5 years ago and now enjoy our annual bareboat charter every year in SVG paradise!"

    Zeljka Gabrovec
    FIVE STARS!

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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!”
Skip HecoxFebruary 2019

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

Scott MckenzieFebruary 2019

“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.”

F HartnettFeb 2018

“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,

Steven HolliApril 2017
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The Basic Learn-’N-Cruise

The Basic Learn-’N-Cruise (LNC) covers the ASA 101, 103 and 104 certifications, the 104 being recognised by charter companies around the world as a Captain’s Licence. We run the courses every week of the year – and up to 5 at the same time. We’re the most active and longest-established ASA sailing school in the south-eastern Caribbean.

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Cruising Catamaran Learn-n-Cruise

(Includes ASA 101, 103, 104 & 114) There are no pre-requisites required for this class. As for the Basic Learn-n-Cruise course, the week starts with the basics and goes through to the 104 certification, recognised as a bareboat skipper’s licence – but with the additional experience of cruising on a 38-to-45 foot catamaran and achieving the 114 cruising catamaran certification.

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Advanced Coastal Cruising Learn-n-Cruise

(ASA 105 & 106) If you already hold the ASA 101, 103 and 104 certifications and are interested in furthering your sailing skills, then the ASA Advanced Coastal Cruising course that we offer is the next logical step. The 9-day cruise includes some night sails in the Leeward and Windward Islands . Prerequisites: Bareboat Charter Certification plus some cruising experience.

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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

  • The Barefoot Navigator

    Barefoot Offshore Sailing School is pleased to announce the first-ever course on barefoot navigation, the use of no-tech and low-tech techniques for wayfinding at sea. Designed by author and veteran sailor Jack Lagan exclusively for BOSS the course will be suitable for beginners as well as ASA- or RSA-qualified navigators. The Barefoot Navigation course will consist of two parts: downloadable materials for pre-study; and one week of practical tuition on board a 40-50 foot vessel (dependant on class size) in the tropical waters of St Vincent and the Grenadines.

  • 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!”
Skip HecoxFebruary 2019

“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,

Steven HolliApril 2017

“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.”

F HartnettFeb 2018

“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

Michael DeppingApril 2017

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

Nic BassonFeb 2018

“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.”

BobFeb 2018

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

Robert & Lindsay HallApril 2017

“Joel was fabulous a great instructor.”

David BrociousApril 2018