Offshore Sailing Courses: ASA 108 & Sail Canada

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.

Our offshore courses are taught by Rob McLean, an instructor at BOSS since 2018. Rob has accumulated over 50,000 cruising miles, with 25,000 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:

Upcoming offshore adventures

Below are our currently scheduled offshore Sailing Adventures and Courses.

Upcoming Nov 29 – Dec 12, 2026

Caribbean World ARC Training Adventure, Late 2026

1,000 miles in two legs: St. Vincent to Sint Maarten along the Windward and Leeward Islands, then a continuous offshore passage back to St. Vincent via Barbados. ASA 106/108 and Sail Canada Advanced/Offshore on both legs.

Upcoming Jan 17 – 30, 2027

Caribbean Sailing Adventure, January 2027

1,000 miles in two legs: St. Vincent to Antigua along the Windward and Leeward Islands, then a continuous offshore passage back to St. Vincent via Barbados. ASA 106/108 and Sail Canada Advanced/Offshore on both legs.

Past adventures

This iconic 2-leg adventure starts in St. Vincent on Jan 25, 2026 and travels 500 miles through the Windward and Leeward islands before arriving in Sint Maarten on Jan 31. Starting Feb 1, it returns to St. Vincent after rounding Barbados, providing an offshore experience out of sight of land. Both legs offer ASA or Sail Canada Advanced and Offshore certification, as well as navigation prerequisites.

This three leg Sailing Adventure travelled from Montreal to Martinique via Halifax and Bermuda

March 2025: This two-leg adventure consisted of a 1 week Advanced course while travelling from St. Vincent to Puerto Rico via the Windward and Leeward Islands, followed by a second offshore leg from Puerto Rico to St. Vincent via Aves Island

January – March 2025: 2 leg passage from Les Sables d’Olonne France to St. Vincent via the Canaries

Oct-Dec 2023: Three-leg sailing adventure from Croatia to St. Vincent via Mallorca, the Canaries, and the Cape Verdes

Oct-Dec 2022: Three leg sailing adventure from Croatia to St. Vincent via Mallorca and Madeira

2021-2024: Multiple 1-week offshore adventures covering 500 miles in a circle from St. Vincent, around St. Lucia, around Barbados, back to St. Vincent

Types of Offshore Courses

Types of Offshore Cruising Experiences

BOSS offers three main types of Offshore Cruising experiences:

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. For details on upcoming offerings, see Offshore Adventures
Week-long Intra-Caribbean offshore courses that begin and end in SVG. For details, see: Intra-Caribbean Offshore Course
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: americansailing.com/certifications/asa-108-offshore-passagemaking/
For Sail Canada Offshore Cruising: 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:

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.
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.
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.
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 (Rob McLean, July 2021)
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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