Sail in the city, master it in Prince Edward County.
Happy Sailing is small on purpose. Four students per course, one boat, one instructor, one week. There is no second classroom. No overflow group. Nobody waiting their turn at the helm while someone else gets the lesson.
It is a Sail Canada certified school, headquartered at Slip 13 of Picton Harbour Marina on Lake Ontario, and a sister operation in Nassau through the winter. Across the 2025 and 2026 seasons we have logged over 5,000 nautical miles aboard Sweetwater, a 2011 Bavaria 36 cruising sloop.
The Intermediate Cruising course is the centrepiece. It is six days liveaboard, departing and returning from Picton, and it is the credential most cruising sailors will use for the rest of their lives.
Featured in Condé Nast Traveler's Best Places to Go 2026 for Prince Edward County. Most schools run six to eight students per boat; you spend half your time watching someone else steer. With us, every student gets real time on the helm.
No. 02 · The cruising ground
Sail Canada is headquartered in Kingston, twenty-five nautical miles east of Picton. This is where Canadian championships and Olympic-class racing happen. It is also where you'll learn to cruise.
An archipelago of small towns and quiet anchorages. Wellington, Waupoos, Bath, Sandbanks, Kingston, the Thousand Islands beyond.
Crossing from Picton to the south shore is thirty nautical miles of open water. This is not a sheltered-bay sailing school.
World-class scale, none of the salt. The boat washes herself.
Sail Canada being headquartered in Kingston is a fact most Toronto sailors don't know. The eastern end of the lake is where the country's elite training, world championships, and Olympic-class racing happen. NYC members training in PEC are sailing in the same waters as the national team.
No. 06 · On the water
Two skill sets, both refined to the Sail Canada Intermediate standard.
Points of sail, tacking and gybing, reefing under way, sail trim with traveler and jib cars, heaving to.
Close-quarters manoeuvring, mooring buoy pickups, spring-line departures, stern-to and side-to docking, standing turn exercises.
Most students see the biggest jump in boat handling under power. By Day 4, springing off a dock in a crosswind feels routine. That is the skill that separates competent cruisers from those who avoid marinas.
No. 09 · What's included
Compare a 7-day BVI bareboat charter at $5,000+ per person before instruction. This is fully instructor-led, all meals aboard, in waters arguably more demanding than the BVI. The value is in the cap of four and the quality of instructor time.