Barefoot Offshore Sailing School
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Course Schedule

The calendar below lists currently scheduled ASA, Sail Canada, BOSS and Instructor Development courses for Barefoot Offshore Sailing School. You can search by Category (ASA, Sail Canada, 106/Advanced, 108/Offshore) and desired month/year. Scroll down to the Sailing School Enquiry form to express your interest in a specific course, enquire about availability, and proceed toward a booking.  If you have specific technical questions, email our Sailing School Coordinator (coordinator@barefootyachts.com) who will get back to you shortly.

Unless otherwise indicated, courses run from 0900 Sunday through noon the following Saturday.

In general, ASA courses are offered year-round.

Sail Canada courses are offered November through April, subject to availability of Sail Canada instructors on base.

[eo_fullcalendar headerCenter=’category’]

If you can’t find a date that works for you, let us know, we are always open to scheduling additional courses.

  • ASA Monohull:  Certifications available – 101, 103, 104
  • ASA Multihull: Certifications available – 101, 103, 104, 114
  • 106/Advanced: Certifications available – ASA 106 and 105(exam) and Sail Canada Advanced Cruising
  • 108 /Offshore: Certifications available – ASA108 and 107/117 (exam), Sail Canada Offshore Cruising
  • SC Monohull: Certifications available – Sail Canada Basic and Intermediate Cruising
  • SC Multihull: Certifications available – Sail Canada Basic and Intermediate Cruising, with the Catamaran Endorsement
  • BOSS High-level Offshore: Certifications available – BOSS High-level Offshore Certificate
  • BOSS Advanced Couples Cruising: Certifications available – ASA 106 or Sail Canada Advanced Cruising, BOSS Advanced Couples Cruising Certificate

Advanced Cruising (ASA 106 and Sail Canada Advanced)

DatesBoat TypeCapacityLink
Oct 8-Nov 15, 2025, 3 legs availableCatUp to 6 participants per legMore info
Jan 25-Feb 7, 2026, 3 legs availableCatUp to 6 participants per legMore info

Offshore Cruising ( ASA 108 and Sail Canada Offshore)

DatesType of BoatCapacityLink
Canada-Caribbean Sailing Adventure, Oct 8-Nov 15, 2025, 3 legs availableCatUp to 6 participants per leg (3 minimum)More info
1000 mile Caribbean Sailing Adventure, Jan 25-Feb 7, 2026, 2 legs availableCatUp to 6 participants per leg (3 minimum)More info
Intra-Caribbean course: TBAMono or catUp to 6 participants (3 minimum)More info

BOSS High-level and Advanced Couples Cruising 

CourseDatesType of boatCapacityLink
BOSS High-Level Offshore CruisingNot currently scheduled (targeting fall 2024)Performance CatUp to 6 students. minimum 3 studentsMore info
BOSS Advanced Couples CruisingNot currently scheduled (targeting fall 2024)Mono or CatUp to 6 students, minimum 2 couplesMore info

BOSS Instructor Development Clinics 

DatesCertifications availableLink
TBA
Sail Canada Instructor clinic including Intermediate, catamaran endorsement, and ASA crossoverrob.m@barefootyachts.com
TBAASA 206, SC Advanced and SC Crossoverrob.m@barefootyachts.com
TBAASA Instructor clinic including ASA 204, 214, 205. rob.m@barefootyachts.com

Until confirmed, course dates and availability are subject to change.  We require a minimum number of bookings in order to confirm a particular course.

Come Sail with Us!

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  • Adaptive Cruise
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  • 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
    • Sail Canada Course Schedule
  • Sail Canada Monohull Cruise-n-Learn
  • Sailing Adventures
    • Advanced Adventures
    • Offshore Adventures
      • Canada – Caribbean Sailing Adventures Fall 2025
      • Caribbean Sailing Adventure 2025
      • Caribbean Sailing Adventure 2026
      • Caribbean Sailing Adventure Early 2027
      • Caribbean World Arc Offshore Training, Fall 2026
      • 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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Recent News

  • Last Minute Sailing School Sale
  • Sailing from Croatia to St. Vincent, Leg 3 (2022 and 2023)
  • Sailing from Croatia to St. Vincent, Leg 2 (November 2022)
  • Sailing from Croatia to St. Vincent, Leg 1 (October 2022)
  • ASA Clinic

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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BOSS Recent Posts

  • Last Minute Sailing School Sale
  • Sailing from Croatia to St. Vincent, Leg 3 (2022 and 2023)
  • Sailing from Croatia to St. Vincent, Leg 2 (November 2022)

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