Captained Charters
Pick your adventure!!
Owner and veteran operated, Sail Ontario is one of the few sailing charter opportunities on Lake Ontario. Now in our sixth year and with over 150 charters, we know exactly how to deliver the sailing moments you deserve and expect! You’ll start your journey at the Madison Barracks Marina, named for President Madison and host to then 2nd Lieutenant Ulyses S. Grant. You’ll spend plenty of time on Lake Ontario, sail past the historic battlefield that saw action in 1812 and 1813, and have plenty of wind. 

At Sail Ontario, everything is included in our up-front pricing.
  • No per person charge
  • Paddleboard, kayak, snorkel gear are always available
  • Customer determined sail plan (with recommendations :)
  • Cold ice box with water and room for your stuff
  • Provisioned lunch (this option does have an additional cost) 

Sail Ontario is proud to honor our service men and women, past and present, and all first responders and law enforcement, with an automatic 10% discount on all services.

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  1. Half Day (~5hrs)
    Madison Barracks to Henderson Bay and/or out to the islands with time for a short stop for swimming and general frolicking about. With departure times at 9 a.m and 2 p.m., pick the morning or afternoon trip - $275
  2. Full Day (~10hrs)
    Enjoy more time under sail more time at anchor, and more time exploring. Cape Vincent and Stony Island are easily in reach. Normal departure time is 10 a.m. - $475
  3. Custom Sail (by the hour)
    Want to try sailing and only feel comfortable with a couple of hours? This is a "you design it" sail where you can sail as long as you want and return when you want. - $65/hr
  4. Sunset (~2 - 2.5hrs)
    Departing at 6:30 p.m. (6 in September), watch the lake's majestic beauty at sunset under sail, lingering in Black River Bay near Horse Island and the historic battlefield. - $135
  5. Moonlight or Starlight (~2hrs)
    This is a unique night cruise, most spectacular around the full moon and new moon times. Departing at 9 p.m. (8 in September), this cruise sails out toward the lake, away from shore lights, to experience a spectacular sky. - $150
  6. Overnighter
    Departing Madison Barracks at 3 p.m. on day one, choose your destination (island anchorages, nearby villages dockside) and enjoy sailing, staying on the boat, fresh cooked meals and local flair. Wake up to the sounds of the lake, enjoy breakfast on board, and return at 2 p.m. on day two. - $500
  7. International Trip
    Two full days, 8 a.m. on day one until 7 p.m. on day two. Enjoy European flavor with shopping and dining in Kingston, ON. - $875
  8. Multi-Day
    Want to spend more than a day at sea? Want to visit several local spots for a night? Care to venture up the St. Lawrence River? Enjoy a private, captained journey to places YOU choose and want to see, or as long as you want. -$400/day plus provisions.

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