Barefoot Offshore Sailing School
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Sail Canada Course Schedule

The calendar below lists currently scheduled Sail Canada courses for Barefoot Offshore Sailing School.  If you can’t find a date that works for you, let us know, we are always open to scheduling additional courses.  Use 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 questions, email our Sailing School Coordinator (coordinator@barefootyachts.com) who will get back to you shortly to respond to your questions.

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

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You can search above by Category (ASA, Sail Canada, BOSS High Performance Cruising) and desired month.

  • ASA Monohull:  Certifications available – 101, 103 and 104
  • ASA Multihull: Certifications available – 101, 103 and 104
  • ASA Advanced: Certifications available – 106 and 105(exam)
  • ASA Offshore: Certifications available – 108 and 107/117 (exam)
  • SC Monohull: Certifications available – Sail Canada Basic and Intermediate Cruising
  • SC Multihull: Certifications available – Sail Canada Basic and Intermediate Cruising, with the Catamaran Endorsement
  • SC Advanced: Certifications available – Sail Canada Advanced Cruising
  • SC Offshore: Certifications available – Sail Canada Advanced Cruising
  • BOSS Advanced Offshore: Certifications available – BOSS Advanced 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 Performance Cruising 

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  • Adaptive Cruise
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  • Intra-Caribbean Offshore Course
  • Offshore Cruising (ASA 108, Sail Canada Offshore, BOSS High-level Offshore Cruising)
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  • Sailing Adventures
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    • 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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