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All listings in Ontario

Incredible sailboat rentals in Ontario, Canada.

4.9
(82 Reviews)

Page 1 of 19 listings

Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$268/hour
Discover Sailing 3hr Introductory Sail
Sailing in Toronto · 4 guests

Discover Sailing 3hr Introductory Sail

4.5
$69/hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$450/hour
41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
Sailing in Toronto · 12 guests

41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

New
$45/hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$300/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$107+/hour
Instant Book
2hr Shared Champagne Sail
Sailing in Toronto · 12 guests

2hr Shared Champagne Sail

New
$85/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 Apr 2026
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
Snoozed - Active 02 Nov 2025

Sailing Reviews in Ontario

  1. BG

    Ben

    Affordable Yacht 27' Doral in Toronto

    Gino and his dad took us out on their boat to the island off the city, where they anchored and we could swim into the beach. We got amazing views of the skyline on the way, and then on the way back they took us even closer to the city before looping back to the dock. Great experience!

  2. RE

    REGINALD

    Hunter 43 Sailing Yacht in Oakville, Ontario

    I will definitely be a repeat customer. Beautiful experience with the wind in the sails and the silence on the water. If you want to enjoy the scenic views of nature then there is nothing better than riding over the water using only the wind. David made it easy for the whole family.

  3. 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!

  4. 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!

  5. 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!

  6. 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.