Barefoot Offshore Sailing School
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Offshore Cruising (ASA 108, Sail Canada Offshore, and BOSS High-level Offshore Cruising)

Offshore Sailing: A unique accomplishment

Beginning in 2021, Barefoot Offshore Sailing School (BOSS) added Offshore Cruising to its roster of course offerings. ASA 108 and Sail Canada Offshore Cruising provide a structured way for a sailor to acquire the knowledge, skills, and experience to plan and implement a significant offshore passage.  BOSS High-level Offshore Cruising courses take you beyond the ASA and Sail Canada Offshore Cruising standards, learning high-level cruising skills on a performance yacht in the southern Caribbean.

Our offshore courses are taught by Rob McLean, an instructor at BOSS since 2018.  Rob has accumulated over 40,000 cruising miles, with 20,000 of these being offshore.  To our knowledge, he is the only offshore instructor that can certify students to both ASA and Sail Canada offshore standards.  Full details of Rob’s sailing journey can be found in his sailing resume.

Articles published in Latitude and Attitudes describing some recent passages in 2022 and 2023 can be found here:

Croatia to St. Vincent, Leg 1

Croatia to St. Vincent, Leg 2

Croatia to St. Vincent, Leg 3

Below are our currently scheduled offshore Sailing Adventures and Courses.

  • France - TransAtlantic Sailing Adventure, Early 2025

    This exciting two-leg adventure includes an Atlantic crossing and offers ASA or Sail Canada Offshore certification.  For qualified candidates a challenge of the Advanced standard may also be possible.  Click for additional details

  • Caribbean Sailing Adventure

    This is a unique 1000 mile sailing adventure from St. Vincent to Puerto Rico and back.  Two legs are available in March 2025:

    1. Leg 1 departs SVG after a day of familiarization and travels north along with Windward and Leeward islands, and BVI and USVI before arriving in Puerto Rico, covering a distance of ~500 miles
    2. Leg 2 departs Puerto Rico and travels directly to St. Vincent in a continuous 500 mile offshore passage.

    For details on this sailing adventure, please see: https://barefootyachts.com/boss/sailing_courses/sailing-adventures/offshore-adventures/caribbean_2024_2025/

  • Intra-caribbean offshore course

    This week-long Intra-Caribbean course offers ASA or Sail Canada Offshore certification.  For qualified candidates a challenge of the Advanced standard may also be possible.  Click for additional details

Types of Offshore Courses

Types of Offshore Cruising Experiences

BOSS offers four main types of Offshore Cruising experiences:

  1. Sailing Adventures: Extended offshore cruising opportunities typically in conjunction with yacht deliveries to SVG from North America or Europe.  The length of these courses depends on the time required to complete the delivery: if longer than 2 weeks, the course will in most cases be sub-divided into two or more legs.  In 2024 we don’t have an Atlantic Crossing but have organized two 1000-mile sailing adventures from St. Vincent to Puerto Rico and back.  For details, see:
  2. Week-long Intra-Caribbean offshore courses that begin and end in SVG.  For details, see: https://barefootoffshore.com/bosssailing_courses/intra-caribbean-offshore-course/
  3. BOSS High-level Offshore Cruising: this unique course takes you beyond the ASA and Sail Canada Offshore Cruising standards, learning high-level cruising skills on a performance yacht in the southern Caribbean.  For details, see https://barefootoffshore.com/bosssailing_courses/boss-high-level-offshore-cruising/
  4. Private Offshore Cruising Courses delivered on the owner’s yacht.  These itineraries are customized based on the location of the yacht.

ASA and Sail Canada Offshore Cruising Standards

Please review the relevant standards as linked below:

For ASA 108:

https://americansailing.com/certifications/asa-108-offshore-passagemaking/

For Sail Canada Offshore Cruising: https://www.sailing.ca/uploads/2021/03/Advanced-Cruise-1-March-2021.pdf

ASA and Sail Canada Offshore Course Components

In accordance with these standards, BOSS Offshore Cruising Courses have four main components:

  1. The standards specify a significant take-home “Ashore Knowledge” assignment that involves carrying out all of the planning required for an offshore passage.  To complete this assignment, a candidate will need to carry out a significant amount of guided and independent research.
  2. Prior to the passage, candidates will draw on this research to carry out specific assignments such as passage planning, provisioning, watch assignments, etc., related to the specific upcoming passage.
  3. Also prior to the passage, a candidate must acquire the skills needed to reduce celestial sights, by completing ASA 107 or 117, or for Sail Canada candidates, SC Celestial Navigation.  These skills are put into practice during the offshore passage.
  4. The on-water portion of Offshore Cruising involves candidates playing a significant role as helmsman and crew for an offshore passage that meets the requirements of the relevant ASA or Sail Canada standard.

Offshore Course Preparations

• Once you sign up for an Offshore Cruising course, we will be in touch to get you started on the Ashore Knowledge assignment. We have compiled a list of resources relevant to the Passage Planning assignment, as well as other texts you might refer to for research purposes.

• We have also compiled a guidance document to help you meet the Celestial Navigation prerequisites:  BOSS Celestial Guidance

• Leading up to the passage, your instructor will be in touch with all participants to discuss course logistics, provisioning, watch schedules, what to bring, and other relevant details.

Course Objectives

  • Planning for an Offshore Passage

    Your Offshore Instructor will coach you through the process of completing the take-home assignment that demonstrates all aspects of planning for an offshore passage that should be undertaken by a prudent sailor.

  • Offshore Certification Prerequisites

    Your Instructor will guide you through the process of acquiring all the prerequisites required for your Offshore ASA or Sail Canada certification, including Celestial Navigation

  • Offshore Skills and Experience

    The on-water component of your Offshore Cruising course will enable you to acquire and practice the skills needed by an offshore sailor, and the experience gained will build the confidence you need to skipper your next offshore passage on your own.

Pricing and Agreements

Pricing depends on which type of offshore experience you are joining.  Details are made available as each offshore opportunity is published.  Pricing has two components: the Base Participation Fee, and Certification Fees based on the certifications sought and earned during the passage.

Base Participation Fee

The Base Participation Fee includes:

  • Shared accommodation on the yacht for the length of the passage.  Given the nature of an offshore passage that requires continuous watches, this may include sharing a berth, hot-bunking, sleeping in the salon, etc.
  • Provisioning: breakfasts, lunches and dinners for the length of the passage, non-alcoholic beverages, some basic snacks
  • Yacht running costs: diesel, water, etc.
  • Access to instruction throughout the passage

The participation fee does not include:

  • Pre-course coaching, marking assignment or exams, processing ASA or Sail Canada certifications, ASA or Sail Canada Membership
  • Travel to or from SVG
  • Personal snacks (since only you know your snacking preferences!)
  • Provisions or dining ashore while in port
  • Cleaning / disinfection fee of $250 per person
  • Alcoholic beverages while in port (consuming alcohol will not be permitted while at sea).  Recreational drugs are not permitted on board

The participation fee can be paid in installments: 50% on booking, and the balance 45 days in advance of the start date of the course.

Certification Fees

Details on certification fees are here.

Crew Agreement

Participants in an offshore passage are required to enter into a Crew Agreement that outlines the mutual responsibilities of the crew and instructor (Master) on the passage.  Details will be shared with you before you book your participation.

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  • 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)
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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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