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All listings in Ontario

Incredible sailboat rentals in Ontario, Canada.

5.0
(85 Reviews)

Page 1 of 15 listings

Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$106/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
$319/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
$195+/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$155+/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. 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!

  2. 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.

  3. EC

    Ehsan

    Sail in downtown Toronto

    We had a great night with Dom. He was very friendly, kind, and easy to talk to, and made the whole experience enjoyable from start to finish. He also took so many great photos of us, and we’ll always have those memories. We had an amazing time and would definitely recommend this tour to anyone. Thanks again, Dom!

  4. ES

    Emily

    Sail in downtown Toronto

    We had an incredible trip on Dom's boat! We went out for my partner's birthday (2 of us). Dom is an amazing host and made us feel welcome from the start. He let us help with the sails and asked our input on where to go based on the wind. We had such a great experience and would recommend him to anyone!

  5. ZF

    Zachary

    Sail in downtown Toronto

    Captain Dom was an incredible host! If I could give 6/5 stars I would. He communication was excellent, he was welcoming, kind, safe and wanted to ensure we all got we needed when on board. His boat is excellent quality and we definitely got more than we asked for. 100% would recommend to anyone, and definitely will do again. Cheers!

  6. BB

    Barbara

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

    David was a most excellent captain. We were having a special send off for someone extremely important to us and David went above and beyond to make sure we all had a great time. He even got out his accordion and sang a song for the woman of the evening which was very funny and very special. We will absolutely book again. Thanks David and Sara!