Sail Prince Edward Bay — Scenic Cruises & Private Charters

Guided sailing departures from Waupoos Marina for couples, families, and groups seeking a relaxed day on the water.

Featured Sailing Trips

Short cruises and private charters designed for sightseeing, swimming, and memorable outings.

Half Day Private Charter

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.

Half Day Private Charter

3 Hour Sailing Adventure

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.

3 Hour Sailing Adventure

boat charters

Picton

2 hr Sailing Cruise

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.

2 hr Sailing Cruise

boat charters

About County Sailing Adventures

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.

County Sailing Adventures — Prince Edward Bay Sailing Experiences

County Sailing Adventures operates from Waupoos Marina in Prince Edward, Ontario, offering scenic sailing cruises and private charters across Prince Edward Bay. These experiences are tailored for couples, families, and small groups who want calm-water sailing, swim stops, and shoreline views.

Why book a sailing cruise in Prince Edward Bay

Scenic waterfront routes departing from Waupoos Marina maximize sheltered sailing and shoreline views.
Private charters provide customizable time on the water for celebrations, team outings, or relaxed family days.
Short and half-day options accommodate travelers with limited time as well as guests who prefer longer experiences.

Trips and what to expect

2 hr Sailing Cruise — Experience a captivating 2-hour sailing adventure on the tranquil waters of Prince Edward Bay. Departing from Waupoos Marina, enjoy stunning views and a relaxing atmosphere, perfect for couples, families, or friends. With an expert crew at your side, create unforgettable memories as you sail through this beautiful region.
Half Day Private Charter — Experience a memorable 4-hour private charter on the stunning waters of South Bay. Ideal for special occasions or team outings, this cruise allows you to sail, anchor, and swim while enjoying snacks and refreshments. Bring your sunscreen and bathing suit for a perfect day of relaxation and fun!
3 Hour Sailing Adventure — Embark on a private 2-hour sailing adventure across the breathtaking Prince Edward Bay. Departing from Waupoos Marina, enjoy serene sailing, refreshing swims, and paddleboarding. Perfect for couples and small groups, this intimate cruise promises relaxation and unforgettable memories amidst stunning waters and lush shorelines. Book your escape today!

Practical details

Departure point: Waupoos Marina (Prince Edward Bay).
Typical durations: 2 hours for short cruises and 4 hours for half-day private charters; specific trip names indicate the experience length.
Activities: scenic sailing, anchoring for swims, paddleboarding on select excursions, and light refreshments on private charters.

Tips for planning

Check the listing on The Adventure Collective for booking availability and up-to-date details.
Bring sunscreen, a bathing suit, and weather-appropriate clothing.
Private charters are recommended for celebrations or corporate outings to secure preferred timing and onboard arrangements.

Keywords for search

County Sailing Adventures, Prince Edward Bay sailing, Waupoos Marina sails, private charter Prince Edward, 2 hour sailing cruise, half day private charter, 3 hour sailing adventure, paddleboarding Prince Edward Bay.

Booking a sail with County Sailing Adventures offers a straightforward way to experience Prince Edward Bay from the water. Whether choosing a short scenic cruise or a private half-day charter, passengers can expect guided sailing, opportunities to swim and paddleboard when conditions permit, and departures from Waupoos Marina with crews focused on safe, enjoyable outings.

Reserve a Sailing Cruise in Prince Edward Bay

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.