Visit The County
Sailing and the County Experience
Partnership Proposal — 2026 Season
Visit The County
Certified sailing on Picton Harbour — an on-the-water experience that gives visitors a reason to stay longer, explore more, and come back.
The County has always been shaped by the water. As we build on what Happy Sailing already offers here, we see an opportunity to make sailing a more visible part of the visitor experience — and to align with where VTC and the region are heading.
Sailing is a hands-on, bookable experience — a natural fit for both the new Experiences page and Lindsay's Water Activities page. It adds a premium, certified tier to the County's on-the-water offerings alongside kayaking, paddleboarding, and swimming.
Our programming aligns with the RTO9 framework around wellness, fitness, and active families. Sailing is an outdoor, nature-based experience that fits the County's identity as a destination for travellers seeking restoration and adventure.
The County's 10-Year Community Plan calls for celebrating its heritage and cultural assets. Sailing is part of PEC's historical tapestry — the waters here have shaped the community since its earliest days through fishing, shipbuilding, and seafaring.
Visitors already come for wine, food, art, and beaches. Sailing can become a more central part of the County experience — connecting newcomers and visitors to the water that has always defined this place.
Visitors are increasingly choosing destinations that offer active, nature-based experiences. The County is well positioned — and sailing can play a bigger role in that story.
Happy Sailing's programming aligns directly with the RTO9 strategic focus on wellness tourism, fitness, and active families — a sector the region is investing in and one that sailing naturally serves.
The Globe and Mail recently noted that PEC visitors are increasingly looking beyond the glass — seeking active, on-the-water, and wellness-focused experiences. Certified sailing is a natural fit for that shift.
Picton Harbour is the County's front door for many visitors. Sailing brings new energy and activity to the harbour, supporting broader efforts to promote it as a destination within the destination.
As the County's tourism story evolves beyond wine and dining, sailing offers visitors a way to experience the water that has always defined this place. It's the kind of activity that extends stays, generates content, and brings people back.
Happy Sailing is a certified sailing academy based in Picton Harbour, offering hands-on cruising education on Lake Ontario.
We teach people to sail — properly. Our courses are certified by Sail Canada, the national governing body for sailing education. Every course is capped at four students for truly hands-on instruction, aboard a comfortable Bavaria 36 cruising yacht.
We also run scenic half-day sails for visitors with no experience — a relaxed morning or afternoon on the water with swim stops, local provisions, and stunning County shoreline views. No sailing background needed.
We've been building relationships across the County that we think support the case for giving sailing a more visible presence in visitor-facing content.
A curated sailing experience for Claramount guests — steps from their boardwalk on Picton Harbour. Couples escapes, corporate retreats, and concierge-recommended add-ons.
We are finalizing a partnership with a large, nationally recognized yacht club in Toronto to bring their members to PEC for liveaboard cruising courses — bringing new visitors directly to the County.
Happy Sailing was mentioned in Condé Nast Traveler's feature naming PEC a top North American destination for 2026, and in The Globe and Mail's piece on Canadian wine regions embracing beyond-the-glass tourism. Visibility is building.
Each of these partnerships creates visitor traffic, content opportunities, and reasons for people to choose the County over competing destinations. Featuring sailing on Visit The County amplifies all of it.
From a casual half-day sail to a multi-day certification course — there's an experience for every type of County visitor.
A relaxed half-day on Lake Ontario aboard our Bavaria 36 yacht. Morning or afternoon departures from Picton Harbour. Swim stops, local provisions, and stunning County shoreline views.
No experience necessary. Perfect for couples, families, or anyone looking for something memorable beyond wine and dining.
Half day · 4-6 guests · No experience neededA hands-on, multi-day Sail Canada certified course. Guests learn to helm, trim sails, navigate, and handle a cruising yacht — a transformative experience that extends their County visit by 3 to 5 nights.
This is what sets us apart from most marine tourism providers. Multi-day courses mean visitors need accommodation, dining, and activities for the full stay — driving real spend across the local economy.
3-5 days · 4 students max · Sail Canada certifiedRomantic half-day sail as part of a County getaway
A hands-on adventure kids and parents do together
Restorative time on the water — blue space therapy
Learn a new skill in a beautiful setting
Practical ways to feature sailing on Visit The County — all designed to fit your new platform and editorial calendar.
We're already listed on Visit The County and would like to build on that foundation. Updated sailing photography, refreshed copy, and direct links to our website and booking page would help visitors find and book us more easily. Longer term, we'd also welcome a presence on the Experiences page as it develops.
Lindsay's Water Activities page is a natural home for certified sailing alongside kayaking, paddleboarding, and swimming. We'd love to contribute content, photography, and copy to help represent sailing as part of the County's on-the-water offerings.
We'd love to explore ways to reach visitors on the ground — whether that's inclusion in the VTC Visitor Centre, rack cards at key locations, placement in seasonal visitor guides and maps, or signage at the harbour and along Main Street.
We'd love to explore ways to reach visitors at the street level in Picton — creative signage, harbour wayfinding, or other ideas that help drive foot traffic from Main Street down to the water. Many visitors don't realize certified sailing is available steps from downtown.
We can provide talking points and quick-reference materials for VTC's new ambassadors — giving them the language to confidently recommend sailing to visitors, explain what we offer, and direct guests to the harbour.
We're happy to supply high-quality content to support your editorial and print needs:
The water has always been part of the County's identity. Making sailing more visible gives visitors another dimension to explore — and another reason to stay.
Sailing connects visitors to the water and maritime heritage that have shaped this place. It gives newcomers and returning guests alike a way to experience the County beyond the shoreline.
Unlike most marine tourism, our courses run 3 to 5 days. That means visitors need accommodation, dining, and activities for the full stay — driving spend across the local economy in a way that single-day experiences don't.
Sailing produces the kind of visually stunning, shareable content that performs well across social media and editorial — golden-hour water shots, harbour scenes, smiling guests at the helm.
Sailing season runs June through October, extending the peak tourism window. Off-season, sailing content and planning keep PEC visible in the minds of prospective visitors.
Regular sailing departures bring energy and activity to Picton Harbour — supporting broader efforts to position the harbour as a vibrant destination for visitors.
With The Claramount Club and a major Toronto yacht club already building sailing-related packages, the ecosystem is forming. VTC promotion ties it all together.
We're ready to support however works best for VTC. Here's what we'd suggest as a starting point.
Reconnect once the new web tools are live to discuss listing criteria and placement
Schedule an early-season on-the-water session to capture sailing footage and photography
We're already on the site — let's explore new possibilities for placement, updated content, and deeper integration as the platform evolves
Content sharing, harbour promotion, and cross-referral throughout the 2026 season and beyond