Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in Ontario

Incredible sailboat rentals in Ontario, Canada.

4.8
(71 Reviews)

Page 1 of 18 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
$324/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
$50/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$158+/hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$300/hour
90min Champagne Sail
Sailing in Toronto · 12 guests

90min Champagne Sail

New
$75/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. PM

    Prince

    Affordable Yacht 27' Doral in Toronto

    Had an amazing experience on the yacht — but honestly, the real highlight was the captain. Super friendly, very patient, and knew exactly where to go for the best views and photos. Even when we were running late, he didn’t rush us at all and made sure we still got the full experience. You can tell he genuinely cares about giving people a good time, not just finishing the trip. If you’re booking this, you’re in safe hands. Highly recommend.

  2. 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!

  3. 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.

  4. 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!!

  5. 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!

  6. 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