Top Toronto Sailing Trips

We had a great sail on a 22' Beneteau. The captain was knowledgeable and comfortable to be with. Our only critique is that the section of lifeline where we board the craft should be detachable so as to provide easier access when boarding as the dock and vessel both float and move with waves.

We didn’t actually leave at 7:30pm so that’s something to note if you’re doing this. Otherwise, it was a very lovely cruise. We loved it

Romantic evening, good sightseeing, friendly staff, happy that the sails went up and good service at the bar! ☺️

We had a lovely time, the captain Howe was fun and he was sharing interesting facts about what we were seeing as well as what the wine and cheeses we were tasting . Emily made beautiful food trays presentations. The extra fun was to sit on the bean bags at the front of the boat to enjoy the view .

Captain Oliver is a capable and friendly l are, and first mate Tamara made everyone feel welcome. Great relaxing way to experience Toronto and the islands.

Yesterday my husband and I celebrated our 11th wedding anniversary here, and it was truly a wonderful evening. This was actually our second experience with Gone Sailing Adventures, and once again we absolutely loved it. The atmosphere on the sailboat is so peaceful and romantic, with beautiful views of Toronto and such a friendly, welcoming crew. It’s the perfect way to escape the busy routine, slow down, and simply enjoy quality time together. Thank you for creating such a memorable experience and beautiful memories for us. We’ll definitely be back and will happily recommend you to our friends. ❤️

This was a beautiful tour around the Toronto islands. The skyline views of Toronto were stunning, the weather was perfect and the crew were entertaining and helped us enjoy the overall experience!

Great time and we loved the two songs that they sang for us!!!

Great experience. Captain very knowledgeable and entertaining. Boat in immaculate condition. Food superb. Highly recommend.

What a great experience! Captain gave good coaching and made everyone comfortable. I’ve sailed my hobie wave a lot but felt somewhat intimidated by “real”sailing on a larger boat. It was a great environment to gain confidence with spectacular views.

I cannot recommend Gone Sailing Adventures highly enough.After a busy week in Toronto filled with meetings, events, and business activities, sailing with Captain Howie was the perfect way to unwind and experience the city from an entirely different perspective.From the moment we stepped aboard, we felt welcomed, safe, comfortable, and relaxed. Captain Howie is knowledgeable, professional, and clearly passionate about both sailing and sharing the stories of Toronto's waterfront. His commentary added depth to the experience, bringing the city's history, landmarks, and skyline to life.What stood out most was the atmosphere he created. The sail felt elegant yet comfortable, social without being crowded, and relaxing without ever being boring. The conversations with fellow passengers were wonderful, and there was something magical about watching the city skyline at sunset while feeling the breeze off the water.This was far more than a boat tour. It was an experience that allowed us to slow down, connect with nature, connect with people, and appreciate the beauty of Toronto from a completely different perspective.If you're visiting Toronto, celebrating a special occasion, entertaining clients, or simply looking for a memorable experience, book the sail.You won't regret it.

Captain ROB and His Helper ROB were excellent part of this trip!! it was a wonderful afternoon sailing the Ontario Lake with beautiful view of Toronto Skyline.

We had the evening tour and the views were absolutely beautiful near the shore. I recommend this tour.

Interesting ship, great views of Toronto and the islands, pleasant crew and office staff. We needed to changie our time and had no problems at all 😊. Great Lakes schooner Company emailed to me excellent directions and a great map of their location! This additional information was very important as the information on the Cool Destinations site appears to be incorrect. Cool Destinations directions brought us to the backside of their office rather than the kiosk for check-in. As mentioned the views were great, and being on the lake was a delight We would’ve welcomed some commentary about what we were seeing in terms of landmarks - however, there was none. Overall, worth the time and resources

Great activity under the sun. Onboard entertainment and good service. It would have been interesting to tour the islands!

Information on sites passing would be helpful as in the history of the sites. The sail was relaxing but the food was expensive and lacking.