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All listings in Toronto

Great sailboat rentals near Toronto, Ontario.

5.0(Average of 94 reviews in this area)
9 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
$56person
35ft C&C 35 Sailboat in Toronto
Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0
$185hour
Sailing Charter in Toronto
Sailing in Toronto · 6 guests

Sailing Charter in Toronto

5.0
Snoozed - Active 17 Apr 2024
A Tropical Experience on a Massive Sailing Trimaran
Sailing in Toronto · 12 guests

A Tropical Experience on a Massive Sailing Trimaran

4.9
$333hour
Beautiful Trimaran for 10 People in Toronto
Sailing in Toronto · 12 guests

Beautiful Trimaran for 10 People in Toronto

5.0
$296hour
Fountain Pajot Astrea Luxury 42' Catamaran for Charter
Sailing in Toronto · 18 guests

Fountain Pajot Astrea Luxury 42' Catamaran for Charter

5.0
$1,000-$1,300hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$400hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$235hour
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
$435hour

Sailing Reviews in Toronto

  1. James
    James
    35ft C&C 35 Sailboat in Toronto

    Peter is a great skipper and host. We thoroughly enjoyed the trip. His boat was spotless and well maintained. He was very knowledgeable about the area and his sailing skills were superb. Certainly would recommend this to anyone especially people never having sailed before.

  2. ES
    Emily
    Sailing Charter in 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
    Sailing Charter in 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. BB
    Barbara
    A Tropical Experience on a Massive Sailing Trimaran

    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!

  5. AD
    Angela
    A Tropical Experience on a Massive Sailing Trimaran

    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.

  6. TB
    Tyanna
    A Tropical Experience on a Massive Sailing Trimaran

    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!!