Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in Toronto

Great sailboat rentals near Toronto, Ontario.

5.0
(29 Reviews)

Page 1 of 18 listings

27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$91+/hour
Discover Sailing 3hr Introductory Sail
Sailing in Toronto · 4 guests

Discover Sailing 3hr Introductory Sail

5.0
$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
$135/hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$69/hour
2hr Shared Champagne Sail
Sailing in Toronto · 12 guests

2hr Shared Champagne Sail

New
$85/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

New
$109+/hour
Instant Book
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 23 Aug 2025

Top Destinations Nearby

Sailing Reviews in Toronto

  1. es

    elomar

    Discover Sailing 3hr Introductory Sail

    It was great to have Gone Sailing with capt Howie! he was extremely knowledgeable about sailing and a patient teacher; strongly recommend and will go direct to him next time I’m in town.

  2. 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!

  3. 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!

  4. GR

    Gordana

    27 Foot Sailboat for a Day of Fun in the Sun in Toronto

    Lee made it an interactive experience for us (family of 4 with two young kids). He was a wonderful host who truly enjoys what he does. My husband wanted to learn, and he shared lots of information making it a cool bday gift for hubby.

  5. Haley

    Haley

    27 Foot Sailboat for a Day of Fun in the Sun in Toronto

    Captain Lee was amazing! I celebrated my 27th birthday with 4 of my friends and had so much fun. A very seamless and fun experience, I will most definitely be recommending to my friends and family.

  6. IP

    Inge

    Sail in downtown Toronto

    Dom is an amazing host! He takes great care of all his passengers with attention to detail from the moment we arrive until the very end. We will book with Dom again for sure!