Sailing Adventures
Upcoming Advanced and Offshore Sailing Adventures
Join our 2-leg Caribbean Sailing Adventures offering Advanced and Offshore certifications: Nov 29–Dec 12, 2026 and Jan 17–30, 2027.
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Barefoot Offshore Sailing School · St. Vincent & the Grenadines
Learn to Sail in the Grenadines
Barefoot Offshore Sailing School – BOSS – is a family business, owned and run by yachtsmen, one of whom is a former America’s Cup sailor whose family has lived here in St Vincent & the Grenadines for many generations.
Instructors
We are recruiting ASA and Sail Canada Instructors
BOSS is always looking for experienced instructors interested in leading courses in one of the best places in the world to teach and learn sailing on keelboats and catamarans. Additional details are here.
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Courses run all year
At 13° North, SVG is south of the path of most named storms. In the rare event that your course is disrupted, BOSS will rebook you for missed time on a subsequent course.
Our scheduleBarefoot Offshore Sailing School in the Grenadines
Learn to sail and cruise in the Caribbean’s most pristine and exciting sailing ground
Enjoy perfect sailing conditions all year. Our instructors are ASA and/or Sail Canada qualified and provide a safe, fun, professional approach to your learning experience.
Why sail with BOSS?
Learn to sail in a true sailor’s paradise!
Diverse Sailing Experiences
Learn to sail in a range of conditions—from protected bays ideal for beginners to open ocean passages for more advanced students. The Grenadines provide real-world experience in various sailing scenarios.
Year-Round Sailing Conditions
The steady trade winds and warm weather in the Grenadines make it possible to sail comfortably year-round, allowing you to learn and practice in consistent, favorable conditions.
Full Range of ASA and SC Certifications
Barefoot Offshore Sailing School is the only school in the Caribbean offering both the complete range of American Sailing Association (ASA) and Sail Canada (SC) certifications, providing flexible learning paths to suit different needs.
Hand-Picked, Expert Instructors
Instructors are carefully selected based on their extensive experience and certification through rigorous Sail Canada and American Sailing instructor programs, ensuring high-quality instruction in accordance with ASA and Sail Canada professional standards. Most have extensive cruising experience on their own or chartered boats, and are equally able to handle situations when things go right, or when they go wrong as occasionally happens. While safety conscious, they also try to make the learning experience fun.
Stunning Learning Environment
The Grenadines offer a visually stunning and diverse environment where you can learn amidst beautiful islands, vibrant reefs, and clear blue waters, turning your sailing education into a memorable adventure.
Practical Skills Development with a Focus on Real-World Scenarios
The varied sailing environments found in the Grenadines—from tight anchorages to open waters—provide ample opportunities for practicing everything from basic maneuvers to more advanced sailing techniques in real-world scenarios.
Small Class Sizes for Personalized Attention
With small class sizes, students receive individualized guidance and support, allowing for a more hands-on learning experience tailored to their pace and level.
Customized Instruction
Our instructors will help you progress as far as possible along the ASA or Sail Canada certification levels. Of course, how far you can get in a single week-long course depends on your starting level of knowledge and skills, previous certifications if any, experience on the water, and aptitude for sailing.
Enhanced Online Course Prep
Students can access improved online materials and resources for pre-course preparation, helping them feel more confident and well-prepared before setting sail.
Practical Training Boats
Barefoot’s primary training fleet includes well maintained boats which are older than 6 years and equipped especially for learning what we need to teach. We place a high emphasis on sailing skills and also living aboard, ensuring a safe and comfortable learning environment while still giving a true cruising experience.
Traditional and Modern Navigation Skills
Our instructors teach traditional navigation skills with paper charts, supplemented by the boat’s electronics and navigation apps on the instructor’s or student’s mobile devices. Traditional navigation skills provide an essential foundation for understanding navigation, as well as provide a backup when electronics fail.
Private Sailing Schools
For those who are looking for a more up market experience we also offer private sailing schools where students can charter a yacht from our Neptune fleet which are all less than 6 years old and receive private instruction from one of our expert instructors.
Post-Certification Mentored Charter Opportunities
After earning your ASA 104 or 114 certification, or Sail Canada intermediate cruising certification, and are ready to begin captaining a yacht without instructor or skipper, we offer our mentor program. This program is designed to help you gain confidence while logging your first miles, in charge of a yacht, required for chartering Barefoot’s extensive fleet for charter yachts. This gives you the chance to immediately put your skills into practice in one of the Caribbean’s top sailing destinations.
Exposure to the Caribbean Way of Life
You will meet residents of many of the islands in the Grenadines, and have the opportunity to understand the challenges and rewards that come from living on semi-tropical islands with a complex history.
Student reviews
What our students say
★★★★★
“If you really wish to learn how to sail, this is hands down, the best place on the planet! We did our courses almost 5 years ago and now enjoy our annual bareboat charter every year in SVG paradise!”
★★★★★
“Excellent sailing school. I completed ASA 101 to 104 with my significant other in April 2017. Fantastic instruction, excellent hands on experience, highly recommend this school. I have the bug now! I want to go sailing every day!”
★★★★★
“Fabulous week – great fun on the sea, discovering islands, whilst learning to sail with great company! Highly recommended! Many thanks to the team!”
★★★★★
“Barefoot Offshore Sailing School offers excellent well trained instructors in a hands on sailing setting. The instruction is rigorous with the perfect balance of relaxation and exploration of the wonderful Grenadines. The courses have increased my sailing aptitude and confidence.”
Last-minute discounts
Spaces left? You save.
Periodically, BOSS offers last-minute discounts when there are available spaces on courses:
| 6 weeks out | 5% · save up to $135 |
|---|---|
| 4 weeks out | 10% · save up to $270 |
| 2 weeks out | 15% · save up to $405 |
After your course
Ready to charter?
Graduates move on to a mentored charter, then a bareboat with our sister company from the same Blue Lagoon base.
Barefoot Yacht Charters →Come Sail with Us!
Our Instructors, some of whom have been with us for many years, are not only certified American Sailing Association and Sail Canada Instructors, but also people who know the islands intimately and are able to get along with folks of all ages and from all walks of life.