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CanadaOntario

Incredible sailboat rentals in Ontario, Canada.

Average of 139 reviews in this area.
1 - 18 of 55 listings

Rent or charter a sailboat for a memorable experience in Ontario.

Are you ready for a fun adventure out on the open water onboard a sailboat in Ontario? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Ontario is a wonderful sailboat rental destination.

Using GetMyBoat to book your next sailing experience.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sailing in Ontario.

  1. CD
    Chaitali
    40' Trimaran Sailing Charter In Toronto with Captain David Playing A Piano Onboard!

    I would definitely recommend to sail with David atleast once. He was funny, warm, great to talk to, and made the whole experience a memorable one.. We went to celebrate my best friend's birthday and boy it was amazingggg!Thank you David for being so kind and fun.. I hope we can do it again..😊😊😊

  2. WD
    William
    40' Trimaran Sailing Charter In Toronto with Captain David Playing A Piano Onboard!

    I would highly recommend David and his boat for anyone looking to enjoy a nice day on the water, work event or celebrate a special occasion. His boat is absolutely beautiful and well maintained. David is very friendly, funny and knowledgeable. Lastly, he played great music and took amazing pictures that captured our special moments on the water. He truly made it a day to remember. 5/5 stars without hesitation!

  3. OB
    Olivia
    40' Trimaran Sailing Charter In Toronto with Captain David Playing A Piano Onboard!

    We celebrated my birthday on David's boat and I must say, it was the best experience ever. My friends and I were fully entertained for the full 4hrs. David did a great job showing us around the harbor, city views, played some songs on his piano and even sang me happy birthday. The boat is very spacious, lots of tanning space ladies. I highly recommend a boat day with him, we will definitely be back next year. Enjoy!!!

  4. JS
    Jasmine
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    Nijole and her husband were just amazing! Even though we were a little late, they welcomed us with enthusiasm and ensured that our time onboard was comfortable and enjoyable. Nijole took great care of us and gave us blankets and pillows to make us comfortable and keep us warm. The couple are super nice and hospitable, very warm and welcoming and made us feel like family. We were celebrating my sister’s birthday and Nijole encouraged her to take a swim in the after too, which she enjoyed immensely. Overall, I would recommend Nijole to host anyone on Harmony! Super fun experience!

  5. SD
    Stuart
    40' Trimaran Sailing Charter In Toronto with Captain David Playing A Piano Onboard!

    David was a great captain - I highly recommend him and his boat. The space on the boat was perfect to relax - he made sure that the scenery was perfect for when we docked to set up a bbq. My team and I confirmed that it was one of the best summer events we have had in a while and we definitely look forward to the next time we get to enjoy an afternoon on the Lake with David!

  6. OY
    Oz
    40' Trimaran Sailing Charter In Toronto with Captain David Playing A Piano Onboard!

    I would wholeheartedly recommend booking your next trip with David. We took a 3 hours cruise on his 40’ trimaran charter and were so happy with the experience. David was professional, responsive to questions, flexible, accommodating, personable and overall a pleasure to work with. He made organizing the cruise such a breeze! The boat was in excellent condition and David’s itinerary took us through parts of the island I hadn’t seen before. Overall, this was an experience we’ll never forget and we’re considering making it an annual event!