Canada-Caribbean Sailing Adventure, Fall 2025

Join us for a sailing adventure of a lifetime, on a remarkable journey from the Montreal, Canada to Martinique in the southern Caribbean on an Excess 11 catamaran.  Three incredible legs are available, each offering its own unique blend of beauty and excitement:

1. Montreal to Halifax (Oct 8-18, 2025), offering Advanced instruction
2. Halifax to Bermuda, Oct 22 – Nov 1, offering Advanced and Offshore instruction
3. Bermuda to Martinique, Nov 5-15, 2025, offering Advanced and Offshore Instruction

This passage is jointly offered by BOSS in collaboration with Ohana Sailing School based in Montreal.  We welcome sailors who wish to join for an exciting sailing adventure, as well as students seeking ASA and/or Sail Canada certifications.

For those seeking certifications:

• Leg 1 will offer ASA 106 and 114, and Sail Canada Advanced Cruising and the SC Catamaran Endorsement
• Legs 2 and 3 will offer ASA 106, 107, 108, 114 and 117, and Sail Canada Advanced Cruising, Sail Canada, Offshore Cruising, the SC Catamaran Endorsement, along with Sail Canada Advanced Navigation and Celestial Navigation.

Space is limited, so act now to secure your spot in this extraordinary expedition!

Travelling down the St. Lawrence River combines challenging navigation because of the tides combined with the river current, as well as spectacular scenery and a high probability of whale-sightings in the region near Tadoussac.  

The Leg 1 itinerary will round the rugged Gaspé peninsula, pass the famous Percé Rick, head south along the New Brunswick coast, travel the Northumberland Strait between Prince Edward Island and Nova Scotia, traverse the Strait of Canso, before heading west along the southern coast of Nova Scotia to the historic Halifax Harbour.

Leg 2 will head due south from Halifax, cross the Gulf Stream at about the halfway point, before making landfall at Bermuda, then navigating the reefs around Bermuda to enter Saint George’s Harbour.

Leg 3 will depart Bermuda and head slightly south-east aiming to pass between the British Virgin Islands and Anguilla, then after entering the Caribbean Sea will skirt St. Martin, St. Barts, St. Kitts and Nevis, passing to the west of Antigua and Guadeloupe, before arriving in the very French island of Martinique.

Skipper / Instructor

Legs 2 and 3 of this sailing adventure will be led by Rob McLean. Rob is uniquely qualified as he holds the distinction of being the only person certified as an Offshore Instructor by both ASA and Sail Canada.  Since the early 1980s, Rob has accumulated more than 45,000 of cruising miles, including 25,000+ miles offshore, on the Great Lakes, Pacific, Atlantic, the Med, and in the Caribbean. Since 2021 he has lead 15 offshore experiences.

In 2021, he completed a 7,000 mile passage from Canada to St. Vincent on his own 62′ schooner, Interlude.  In 2022 he led a 5,400 mile three-leg passage from Croatia to SVG in the Caribbean.  In spring 2023 sailed Interlude 2,000 miles from SVG to Halifax in Canada via Bermuda. In Oct-Dec 2023 he led another three-leg crossing from Croatia to SVG, via Mallorca, the Canaries, and the Cape Verdes. In early 2025, he led a 2-leg passage from France to the Canaries, then on to St. Vincent.

As a Senior Sail Canada Instructor Evaluator and  ASA Master Instructor, he leads instructor development clinics for both Sail Canada and ASA.

His full sailing resume is here: http://robmclean.ca/sailingresume.html .  His professional background outside of sailing is summarized here: http://robmclean.ca/Resume.shtml

Expressions of Interest

If interested, please contact Rob McLean at rob.m@barefootyachts.com, including a brief summary of your sailing certifications and experience, and indicating which leg or legs you are interested in.  We will then schedule an interview to confirm that this adventure is right for you.  Assuming “yes”, we will then issue a formal registration invitation, along with full details of the passage, how to prepare, what to bring, and the sign-up procedure.