Guided sailing departures from Waupoos Marina for couples, families, and groups seeking a relaxed day on the water.
Short cruises and private charters designed for sightseeing, swimming, and memorable outings.
boat-charters · Picton
Discover the beauty of Lake Ontario with a private boat tour in Picton, Ontario. Enjoy personalized experiences, stunning scenery, and wildlife encounters on this relaxing half-day adventure.
County Sailing Adventures is a Prince Edward, Ontario–based sailing provider offering guided and private cruises on Prince Edward Bay. Operating from Waupoos Marina, the company runs short public sails and private charters that showcase the region’s shoreline, calm waters, and seasonal wildlife.
Trips include a 2 hr Sailing Cruise for couples, families, and friends; a Half Day Private Charter that provides a four-hour customizable outing for celebrations, corporate groups, or relaxed days on the water; and a 3 Hour Sailing Adventure designed for small groups seeking swimming, paddleboarding, and intimate time afloat. Experienced crew members handle navigation, safety briefings, and sail operations so guests can focus on scenery and comfort.
Vessels depart from Waupoos Marina, with routes planned to maximize sheltered sailing in Prince Edward Bay and opportunities to anchor for swimming and paddleboarding when conditions allow. Refreshments and light snacks are available on private charters, and passengers are encouraged to bring sunscreen and bathing suits. County Sailing Adventures emphasizes safe, enjoyable experiences with attention to weather, local navigation, and guest needs.
The business caters to a range of occasions, including date outings, family excursions, and team events, and offers private bookings for more control over schedule and activities. Reservations are recommended, especially for private charters and weekend dates. For accurate availability and booking details, prospective guests should consult the business directly or visit the listing on The Adventure Collective. Timely communication and transparent pricing are provided through the listing to help guests plan their sailing experience and confirm availability.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Departs Waupoos Marina
Short sails and half-day charters
Ideal for groups and events
Scenic sails and swim stops
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current County Sailing Adventures listing.
County Sailing Adventures offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Choose a 2 hr Sailing Cruise, a 4-hour Half Day Private Charter, or the 3 Hour Sailing Adventure — check availability on the listing and book today.
boat-charters · Picton
Discover the beauty of Lake Ontario with a private 3-hour sailing cruise from Picton. Perfect for relaxing, sightseeing, and wildlife watching, this adventure offers an unforgettable day on the water.
boat-charters · Picton
Set sail on a private 2-hour sailing cruise in Picton, Ontario, with County Sailing Adventures. Enjoy stunning views, wildlife sightings, and a personalized sailing experience perfect for any occasion.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.