Barefoot Offshore Sailing School
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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

  • “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.”

    Skip – Feb 2019

  • "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 in the Grenadines!

BOSS offers a full slate of week-long courses offering ASA certifications.  Click any item below for full details.

  • Monohull Learn-n-Cruise: Offers ASA 101 Basic Keelboat, 103 Basic Cruising, 104 Bareboat Cruising
  • Catamaran Learn-n-Cruise: Offers ASA 101 Basic Keelboat, 103 Basic Cruising, 104 Bareboat Cruising, 114 Catamaran Cruising
  • Advanced Learn-n-Cruise: Offers ASA 106 Advanced and optionally the exam for 105 Coastal Navigation
  • Offshore Cruising: Offers ASA 108 Offshore and optionally the exam for 107 or 117 Celestial Navigation

In response to requests from the many Canadians that participate in BOSS courses, in 2018 BOSS became the only registered Sail Canada school outside Canada, and recruited a roster of leading Sail Canada instructors who are all cross-qualified with ASA.

Sail Canada courses, which are available November through April, include:

  • Sail Canada Monohull Learn-n-Cruise: Offers Sail Canada Basic and Intermediate Cruising certifications
  • Sail Canada Catamaran Learn-n-Cruise: Offers Sail Canada Basic and Intermediate Cruising with the Catamaran Endorsement certification
  • Sail Canada Advanced Learn-n-Cruise: Offers Sail Canada Advanced Cruising certification
  • Sail Canada Offshore:  Offers Sail Canada Offshore Cruising certification

Building on its 20 years of experience and the unique ocean racing qualifications of Philip Barnard, Barefoot’s Managing Director, BOSS has developed some special courses that build on but go beyond the ASA and Sail Canada standards.

BOSS Special Courses include:

  • BOSS High-level Offshore Cruising: offers unique training and experience on a performance yacht that goes beyond the ASA and Sail Canada Offshore standards
  • BOSS Advanced Couples Cruising: teaches cruising couples the knowledge and skills they need for safe and efficient short-handed sailing
  • BOSS Emergency Navigation: teaches you how to navigate to safety even if all your electronics fail while offshore
  • BOSS Yachtsman’s Diesel Engine Course: teaches the hands-on skills needed to keep your diesel running safely and efficiently
  • BOSS Yachtsman’s Rig-tuning Course: teaches the hands-on skills needed to tune and maintain your rig

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

“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

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.  Advanced course, April 2022

Joe Ziolkowski

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“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
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  • Adaptive Cruise
  • ASA Sailing Courses
  • BOSS Course Agreement Terms
  • BOSS High-level Offshore Cruising
  • BOSS Offshore Sailing Adventure Certification Fees
  • BOSS Special Courses
  • Couple- Sailing / Double handed sailing courses
  • Course Schedule
  • Intra-Caribbean Offshore Course
  • Offshore Cruising (ASA 108, Sail Canada Offshore, BOSS High-level Offshore Cruising)
  • Sail Canada Catamaran Learn-n-Cruise
  • Sail Canada Courses
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  • Sail Canada Monohull Cruise-n-Learn
  • Sailing Adventures
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    • Offshore Adventures
      • Caribbean Sailing Adventure 2025
      • France – TransAtlantic Sailing Adventures Early 2025
      • Mediterranean – Trans-Atlantic Sailing Adventures Fall 2022
      • Mediterranean – Trans-Atlantic Sailing Adventures Fall 2023
  • Short Handed Cruising Course Couples Cruising – Coastal, Offshore
  • Advanced Coastal Cruising Learn-n-Cruise
  • ASA Catamaran Learn-n-Cruise
  • ASA Monohull Learn-n-Cruise
  • ASA or Sail Canada Beginner Course
  • BOSS’s Yachtsman’s Diesel Engine Course
  • BOSS’s Yachtsman’s Rig Tuning Course
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BOSS Last Minute Discounts

Periodically, BOSS offers last minute discounts when there are available spaces on courses as follows:

6 Weeks 5% discount save up to $135
4 Weeks 10% discount, save up to $270
2 weeks 15% discount, save up to $405
To view available discounts, monitor the “Specials” slider on the BOSS homepage

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