Offshore Adventures › Late 2026
A 1,000-mile offshore adventure from St. Vincent to Sint Maarten and back via Barbados, November 29 to December 12, 2026.
Join us for a 1,000-mile offshore adventure from St. Vincent to Sint Maarten and back via Barbados, from November 29 to December 12, 2026. Two legs are available, each with its own mix of island scenery and open-ocean sailing:
BOSS offers ASA 106 and 108, and Sail Canada Advanced and Offshore certifications, on both legs. Leg 1 is better suited to Advanced certifications because we'll be in sight of land most of the time. Leg 2 is largely offshore, out of sight of land. Space is limited.
The owners of the yacht are preparing to take part in a future World ARC, so the curriculum includes activities that support that goal.
Sail waters contested for centuries by European powers and home to generations of buccaneers. Today they're enjoyed by island residents and by visitors who come for Caribbean sun, warm water, trade winds and beautiful scenery.
Vessel: Inconceivable, a 4-cabin 50′ Leopard catamaran.
Standards: ASA · Sail Canada
Capacity: Maximum 6 participants per leg, plus the skipper/instructor.
Rob McLean leads these adventures. He is the only person certified as an Offshore Instructor by both ASA and Sail Canada.
Since the early 1980s Rob has logged more than 50,000 cruising miles, including more than 25,000 offshore. He has sailed on the Great Lakes, the Pacific, the Atlantic, the Mediterranean and the Caribbean, and made Atlantic crossings in 2022, 2023 and 2025.
As a Sail Canada Senior Instructor Evaluator and ASA Senior Master Instructor, Rob leads instructor development clinics for both organizations.
Sailing resume · Professional background
Planned itinerary, subject to change for weather or other events. Prices are the base participation fee in USD.
Nov 29–Dec 5, 2026 · ~500 nm along the Windward and Leeward Islands
See the Windward and Leeward Islands, known to generations of explorers, buccaneers and cruising sailors. We chose Sint Maarten as the changeover point because it's one of the easiest islands to fly into. There should be time to loop around most, if not all, of the Leeward Islands.
Dec 6–12, 2026 · ~500 nm continuous offshore passage
Leave Sint Maarten on a continuous offshore passage to Barbados, then return to St. Vincent. We'll navigate by celestial means, with multiple GNSS devices on board.
Base fee
