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All listings in Ontario

Incredible sailboat rentals in Ontario, Canada.

4.9
(82 Reviews)

Page 1 of 19 listings

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
$320/hour
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$267/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

Sailing Reviews in Ontario

  1. 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!

  2. 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.

  3. 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!!

  4. 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!

  5. NN

    Natalie

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

    Thank you for an awesome Ride. 12 ladies who just needed a quick break. Dave was easy to connect and communicate with. It was a very easy and comfortable sail. We had our own little celebration and he fit right into our group. Highly recommended and will definitely be booking with him again. Thanks Dave

  6. 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.