Welcome to Barefoot Offshore Sailing School!

Sailing School

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.

There are usually no more than 4 guests plus the Instructor, but occasionally there may be a 5th.  All guests have their own cabin.  We run the cruises every week of the year on catamarans and monohulls between 38 and 50 feet.

Celebrating 20 Years of B.O.S.S

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.

Basic Sailing to Bareboat Charter Certification Learn-n-Cruise in the Grenadines

(ASA 101, 103, & 104). No prerequisites. Starts with the basics and leads through to the 104 certification which is recognised as a bareboat skipper’s licence anywhere in the world.


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.


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.


Sailing with Barefoot Yacht Charters

Experience St Vincent and the Grenadines!

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.

Barefoot Offshore 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.

Our specialization

ASA Certified Sailing School
Yacht Charter and Marine Centre
Yacht Management Services
Crewed Yacht Charters

Testimonials from some of our Barefoot Offshore Sailing Schools

Doralene Deokielal

“Our Instructor was great, he was firm and patient and absolutely amazing. He built my confidence and strengthened my weaknesses”

Doralene Deokielal17th-23rd July 2016, on "LA MOUETTE"
 Louis Jensen

“Extremely pleased with the entire experience, we learned a great deal and had a terrific time in the process”

Louis Jensen 10th – 16th July, 2016 on "TARSHA"
Erika Stewart

“Overall it was a really awesome week. Mike was an excellent instructor. I always felt safe and learnt a lot.”

Erika Stewart3rd - 9th July, 2016 on "SATYRUS"
David McPhee

“Chris was an excellent instructor, fun to be with and always teaching!” ,

David McPhee19th – 26th June 2016, on "INORDINATE"