The 4 Best Sailing Trips in Canada

1.Toronto Tall Ship Boat Cruise

★★★★★★★★★★4.5 · 676 reviews · 2 hours (approx.) · from $38Our pick

Sail Toronto Harbour aboard the historic Tall Ship Kajama, a three-masted 1930s schooner. Allow 30 minutes for boarding, then help raise the sails, hear sea shanties, watch the cannon fire, and enjoy 90 minutes on Lake Ontario with skyline and Toronto Islands views. Food and drinks are extra.

“It was good and the only thing that could be improved would making the trip longer. I would limit the volume on purchasing booze. The whole boat knew their life stories of 2 girls and 2 guys”

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2.Tall Ship Silva Sailing Cruise Ft. a Live Musician

★★★★★★★★★★4.0 · 289 reviews · 2 hours (approx.) · from $40

Spend about two hours aboard the Tall Ship Silva, sailing from Halifax’s waterfront past the Harbour Bridge, Cable Wharf, Georges Island, Fort George, and McNab’s Island. A live musician performs onboard, drinks are available for purchase, and you may help raise the sails. Dress warmly, arrive early, and expect a relaxed harbour cruise with occasional engine use.

“If you don't do this cruise you will miss out on a great experience. High lite of our Halifax visit.”

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3.JFarwell Sunset Wine and Cheese Yacht Sailing

★★★★★★★★★★5.0 · 149 reviews · 2 hours 30 minutes (approx.) · from $150Top rated

Spend 2.5 hours aboard the JFarwell sailboat with captains and crew such as Ryan, Finn, Andrew, and Ali. Taste four Nova Scotia wines, including Tidal Bay, with local charcuterie while sailing from Halifax Waterfront toward George’s Island, McNabs Island, and the Northwest Arm.

“I had an amazing time on this sailing trip.It was a georgous summer day with a spectacular sunset!Brendon,Maryam and Avery did a fantastic job in hosting the sailing tour.Brendon and Maryam explained very well the area and Avery did a great job in explaining all the diffrent wines which were served on the tour together with cheese and snacks.I highly recommend this tour to everyone who visits Halifax!Thanks for a great sailing experience!”

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4.JFarwell Adventure Yacht Sailing in the Halifax Harbour

★★★★★★★★★★5.0 · 147 reviews · 1 hour 30 minutes (approx.) · from $82

Spend about 90 minutes sailing Halifax Harbour aboard a yacht limited to 12 people. The crew, including captains such as Ryan, Jeff, and Frankie, invites you to help raise sails, steer, and assist with tacks. You’ll see Georges Island and the waterfront from the water, with Nova Scotia drinks available to purchase onboard.

“Brandon and Margaret were great hosts. Great way to spend a couple hours. Actually met another couple on a boat which led to dinner and drinks . Great way of meeting people”

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