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All listings in Ontario

Incredible sailboat rentals in Ontario, Canada.

5.0
(70 Reviews)

Page 1 of 14 listings

Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$118/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
$317/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$154+/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. 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!

  2. 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!

  3. 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!

  4. AD

    Angela

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

    Dave was an incredible host. He was pleasurable, outgoing and fun. Kim, his deck hand, was also extremely helpful and friendly. My friends and I had an amazing time celebrating my birthday. The boat is beautiful and Dave offered us some of the best views of the city. I’m extremely thankful for this positive experience. Thank you very much for the hospitality.

  5. TB

    Tyanna

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

    I booked David’s boat on Saturday for my birthday celebration! The boat is phenomenal and had a lot of space! Both Kim and David were excellent hosts, they assisted us throughout the whole trip! Would highly recommend booking with David! I would most definitely book another yacht trip with David and Kim!!

  6. SG

    Samantha

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

    Had an amazing time with Captain David for my birthday on the water! Everything was extremely easy from booking the boat to getting there I would highly recommend this for those of you looking for an experienced captain and team. Thanks for making my birthday so memorable!