Happy Sailing
It's YOUR day on the water :)
Hallowell
Happy Sailing offers sailing experiences on Picton Bay and Eastern Lake Ontario, departing from Picton Harbour aboard Sweetwater — a spacious, beautifully maintained 2011 Bavaria 36.
Groups of up to 6 guests. No sailing experience needed. Whether you're after a relaxed afternoon on the water, a sunset sail, a swim stop in a quiet bay, or a full day out on the open lake, we'll make it happen. Private bookings available.
"Evan went above and beyond from start to finish. Safety conscious and FUN — and an amazing chef." — Google Review
"We LOVED our day sailing with Happy Sailing. Evan greeted us with a smile and continued to provide a beautiful experience for us throughout the entire experience." — Google Review
Eastern Lake Ontario is some of the best freshwater sailing in the world — big winds, clear water, dramatic skies. Most people don't realize what's out here until they're on it.
Named in Condé Nast Traveler's Best Places to Go in 2026 feature on Prince Edward County.
We acknowledge that Prince Edward County rests within the ancestral lands and waters stewarded by the Michi Saagiig Nishnaabeg (Mississauga), Huron Wendat, and Haudenosaunee. This is a place shaped by their presence, languages, and care since time immemorial. To acknowledge this land is to recognize our responsibility to live as good relatives with each other, with the earth, and with the generations yet to come.