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All listings in Ontario

Incredible sailboat rentals in Ontario, Canada.

5.0
(93 Reviews)

Page 1 of 15 listings

Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$108/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$324/hour
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests

5.0
$198+/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$158+/hour
Sail the 30,000 islands in Georgian Bay aboard 40' Beneteau Sailboat
Sailing in Parry Sound · 6 guests

Sail the 30,000 islands in Georgian Bay aboard 40' Beneteau Sailboat

New
$141/hour

Sailing Reviews in Ontario

  1. AB

    Alan

    Sail in downtown Toronto

    Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.

  2. KD

    Katherine

    Sail in downtown Toronto

    We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!

  3. GK

    Galina

    Sail in downtown Toronto

    Dom is a great and hospitable captain. He was very kind, he offered drinks, always checked with what we would like to see and was ready to offer alternatives. I would highly recommend his services!

  4. Kim

    Kim

    Sail in downtown Toronto

    Dominic was incredible! He was so chill and so kind with our family. It was a perfect day out sailing on the water. He taught us so much, shared stories, local history and was genuinely so sweet with our family, taking pictures and showing us points of interest! A PERFECT EXPERIENCE AND A PERFECT DAY!

  5. HD

    Harry

    Sail in downtown Toronto

    Dom was amazing he takes great pictures was Betty accommodating and gave us lots of fun facts! Was a beautiful experience overall!

  6. CP

    Colleen

    Sail in downtown Toronto

    We had a fabulous afternoon sailing with Captain Dom. He was very welcoming, friendly and knowledgeable. We immediately felt safe and comfortable sailing with him. The boat was clean and very comfortable and the vibe was relaxing and chill. We enjoyed being out on the lake with the great views of the skyline. It’s a great way to unwind and spend some quality time with some family or friends. I would definitely recommend this experience and I will be booking again to sail with Captain Dom.