Caribbean Sailing Courses

Weeklong Live-Aboard Courses
Sunday 10am – Saturday 1pm

Don’t miss out on our 20 Years of B.O.S.S special! This year we are celebrating our 20th year as the Barefoot Offshore Sailing School and to thank everyone for their support over the years, we are offering 10% off of all schools that are running between now and the 29th October 2016! For more information please send us an email at

Our weeklong live-aboard learning vacations give students hands-on experience while exploring the exotic islands of the Grenadines. We offer beginning, advanced and catamaran courses that teach you what you need to know to charter your own yacht anywhere in the world.

In the beginning course, with pre-study and a desire to learn, students can achieve bareboat charter certification in just one week.  We limit course size to four to five single students, three couples or a mix between and one instructor as you live aboard a beautiful 40 to 50 foot yacht.

  • Cruising Catamaran Learn-n-Cruise (Includes ASA 101, 103, 104 & 114) There are no prerequisites required for this class. Just like in the Basic Learn-n-Cruise course, we will start out with the basics and take you all the way through Bareboat Charter Certification, the difference this time is that we will be doing it on a 38 to 45 foot Cruising Catamaran. In addition to Bareboat Charter Certification you can also earn your Cruising Catamaran Sailing Certification.
  • Cruising Catamaran Certification (Includes ASA 114). Prerequisite for this class is ASA 104 Bareboat Charter Certification. This is a two day class for students who already have their ASA Bareboat Charter Certification, and would like to explore the option of chartering a Cruising Catamaran.  This class can easily be done at the beginning of a charter on board one of our boats. After completing the class, drop off your instructor and continue on your Cruising Catamaran sailing vacation.
  • Advanced Coastal Cruising Learn-n-Cruise (ASA 105 & 106) If you already have earned your ASA Bareboat Chartering Certification and are interested in furthering your sailing skills, ASA Coastal Navigation and Advanced Coastal Cruising is a great place to start. This class will include night sails between several of the Windward Islands with warm winds and beautiful stars to guide our way. Prerequisite: Bareboat Charter Certification plus some cruising experience.

Barefoot Offshore’s 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.

We at Barefoot Yacht Charters and Barefoot Offshore Sailing School recommends SailX to our clients and student sailors, many of whom come back to the beautiful Grenadines time and again to develop their offshore sailing skills: Our Management Team and Instructors believe it helps with understanding basic rules of the road and the effects of wind and current on the sea as well as when using this fun, engaging and instructional sailing simulator. Please feel free to give it a try! You’ll be amazed at how much you can pick up, even before taking a step onto a boat!

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