Prince Edward County
Your Day on the Water
Step aboard. Leave the shore behind. Discover the County from its most beautiful angle.
Explore ExperiencesNot a Classroom.
An Experience.
Happy Sailing brings together the best of Prince Edward County's coastline with genuine hospitality. Whether you're curious about sailing or just want an unforgettable day out, our experiences are designed around you — your pace, your people, your kind of adventure.
Every trip departs from Historic Picton Harbour aboard our modern 36-foot cruising sailboat. Add on a locally-sourced charcuterie board, lunch, or refreshments when you book — we'll have everything ready when you step aboard.
Choose Your Experience
Three Ways to Get on the Water
3 Hours The Afternoon Sail
A perfect first taste of sailing. Feel the wind, take the helm if you'd like, and see Prince Edward County from a perspective most never do. Ideal for date nights, casual outings, or simply satisfying your curiosity.
5 Hours The Half-Day Escape
More time means more coastline, a swim stop at a hidden cove, and the option to add a locally-sourced lunch aboard. This is the one our guests come back for — unhurried, sun-soaked, and genuinely restorative.
Full Day The Private Day Sail
The whole boat is yours. Up to six guests, a dedicated skipper, and a day tailored entirely around your group. Whether it's a birthday, a proposal, a team outing, or just an incredible day with friends — this is how you do it.
The Details
What to Expect
Every experience includes the essentials. You just show up.
Professional Skipper & Host
Your captain handles everything — you're here to enjoy the ride.
Modern 36ft Sailboat
A well-equipped Bavaria cruiser — comfortable, spacious, and built for these waters.
Provisioning Add-Ons
Charcuterie, lunch, refreshments — add them at booking and we'll have it ready.
Hidden Coves & Swim Stops
We know these waters. Expect anchorages and swim spots most people never find.
Small Groups Only
Maximum six guests per trip. No crowds. Personal attention, always.
Historic Picton Harbour
Easy access, free parking, and the best departure point in the County.
From Our Guests
What People Are Saying
We LOVED our day sailing with Happy Sailing. Evan greeted us with a smile and continued to provide a beautiful experience for us. We mostly enjoyed the serenity of the water, the quiet, the conversation, and that delicious swimming water — and snack!
We had the most amazing sunset sail with Evan. It was spectacular in every way — the swimming, the meal Evan prepared, a beautiful memorable evening.
We had an absolutely amazing experience! Evan was a wonderful host and made us feel completely safe and comfortable. We did the 3-hour sailing tour and anchored at a gorgeous spot and enjoyed a lovely light lunch. Highly recommend!
A birthday surprise from my daughter — a fabulous sail with Evan off Waupoos Island to Little Bluff. Yummy snacks too. It's a special experience on our beautiful Lake Ontario!
Ready for Your
Next Adventure?
Questions about provisioning, group bookings, or special occasions? We'd love to hear from you.
Get in Touch