CanadaOntario

Incredible sailboat rentals in Ontario, Canada.

Average of 113 reviews in this area.
1 - 18 of 32 listings
32 results

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. JB
    Jacki
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    We had a wonderful time sailing with Nijole and her husband Remus (I probably spelled that wrong, apologies!). Lake Michigan and views of Chicago are stunning, we had perfect weather, and the boat and her crew were wonderful. Highly recommended, especially as a somewhat "physically distanced" option in these times.

  2. SC
    Sheana
    Monday - Thursday Charters (excluding Holidays) $1200 for 3 hours saving you $300! Friday - Sunday $1500 per 3 hours. .

    David was a GREAT host, and the boat is incredible. Between himself and the Stewardess, Kim (who is incredibly kind, fun, and helpful!) it was the perfect luxury boat day. There was more than enough space for 12 people, and we had such a great time we extended the trip for 2 hours. You will undoubtedly have an AMAZING time******

  3. Mk
    Matthew
    Monday - Thursday Charters (excluding Holidays) $1200 for 3 hours saving you $300! Friday - Sunday $1500 per 3 hours. .

    David, was an excellent captain and sailed us around the Toronto bay, and anchored near Hanlan's beach .We had a perfect day. We were a party of 6, and there was ample space for at least 10. I would highly suggest David, for any boat rental in the future and look forward to our next charter with him.

  4. ND
    Nancy
    Charter a 31' Pearson Cruising Sloop, Chicago

    We had a wonderful time with Captain Joey! The weather was perfect for cruising around and sailing. The Captain showed us beautiful views of the city skyline and there was never a dull moment on board. I would definitely book again with Captain Joey and recommend others to do so too.

  5. JS
    Jasmine
    Monday - Thursday Charters (excluding Holidays) $1200 for 3 hours saving you $300! Friday - Sunday $1500 per 3 hours. .

    Had a great experience on David’s boat! It was the perfect size to accommodate our larger group and we felt very comfortable on it. David listener to our requests and took us on a great route along centre island and harbour front. Would highly recommended for anyone interested!!

  6. MM
    Milad
    Monday - Thursday Charters (excluding Holidays) $1200 for 3 hours saving you $300! Friday - Sunday $1500 per 3 hours. .

    I booked this trip for my Wife's birthday and it was a fantastic experience even in these difficult times when activities are rare to come by. David was kind, friendly and accommodating to our request as well as a gracious host. His boat was clean and well-maintained with having some comfortable pillows to lounge on the mesh laying area. David started singing with his piano for us and the whole group sang along and had a great time. What a wonderful experience, we will definitely be booking with him again.