Update: This Sailing Adventure concluded on November 20, 2025 when we arrived safely in Martinique. We were a few days late because in Leg 2 we needed to divert to New York City for 4 days waiting for Hurricane Melissa to pass by Bermuda.
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:
- Montreal to Halifax (Oct 8-18, 2025), offering Advanced instruction
- Halifax to Bermuda, Oct 22 – Nov 1, offering Advanced and Offshore instruction
- 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!
About the Adventure
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 Rock, 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 led 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. His professional background outside of sailing is summarized here.
Certifications
For details on relevant standards, see: ASA standards · Sail Canada standards
Note that given the extensive certification requirements Advanced and Offshore cannot be combined on the same leg. ASA 114 / SC Catamaran Endorsement can be combined with Advanced or Offshore.
Maximum capacity on each leg is 6 participants, plus the skipper/instructor.
Pricing
The Base Participation Fee (USD) for each leg or combination of legs is as follows:
Planned Itinerary
Please note that details below are subject to change based on the impact of weather or other events on the schedule, and availability of marina space in the chosen destinations.
Leg 1
Montreal to Halifax
Oct 8-18, 2025 · Distance: 1100 miles
We will depart from Montreal and then head 550 miles downstream to round the Gaspé peninsula. Travelling down the St. Lawrence is a truly iconic experience, given the enormous importance of this massive river in Canadian history. From the Gaspé we will head south along the coast of New Brunswick, passing the famous Percé Rock, pass Chaleur Bay, then navigate the Northumberland Strait between Prince Edward Island and Nova Scotia. Our course then takes us through the Canso Strait between the Nova Scotia mainland and Cape Breton Island, before turning west along the southern shore of Nova Scotia aiming for the historic port of Halifax.
- Certifications
- ASA 106 / Sail Canada Advanced Cruising · ASA 114 / Sail Canada Catamaran Endorsement · ASA 105 or Sail Canada Intermediate navigation exams if required as prerequisites
- Base fee
- $3,995 USD
Leg 2
Halifax to Bermuda
Oct 22 – Nov 1, 2025 · Distance: ~800 miles
Bermuda is almost due south of Halifax. We will cross the Gulf Stream at about the halfway mark. This will be an open ocean experience, navigating by celestial means as well as modern electronics. Bermuda is surrounded by extensive coral reefs, which in previous centuries resulted in countless shipwrecks. The entrance through the reef is now well marked but can be a bit boisterous as it is at the north-eastern corner of the island. Saint George’s Harbour, our destination, is a charming location combining old-world Bermuda architecture with modern conveniences.
- Certifications
- ASA 106 / Sail Canada Advanced Cruising · ASA 108 / Sail Canada Offshore Cruising · ASA 114 / Sail Canada Catamaran Endorsement · ASA 105, 107, 117 exams, or Sail Canada Intermediate, Advanced and Celestial navigation exams if required as prerequisites
- Base fee
- $4495 USD
Leg 3
Bermuda to Martinique
Nov 5-15, 2025 · Distance: ~1100 miles
Leg 3 will depart Bermuda and head slightly south-east, aiming to pass between the British Virgin Islands and Anguilla. This will be an open ocean experience, navigating by celestial means as well as modern electronics. Once we enter the Caribbean Sea, we 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.
- Certifications
- ASA 106 / Sail Canada Advanced Cruising · ASA 108 / Sail Canada Offshore Cruising · ASA 114 / Sail Canada Catamaran Endorsement · ASA 105, 107, 117 exams, or Sail Canada Intermediate, Advanced and Celestial navigation exams if required as prerequisites
- Base fee
- $4495 USD
