Under sail · CANADA SAILING TOURS

Sailing in Canada: the 5 Best Trips

5 sailing trips  ·  seats from $34 each

The coast of Canada from the water: 5 sailing trips with their prices, how long each is out and what is served on deck.

Toronto Tall Ship Boat Cruise - Helping the crew raise the sails
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Toronto Tall Ship Boat Cruise

1.Toronto Tall Ship Boat Cruise

★★★★★★★★★★4.5 · 676 reviews · 2 hours (approx.) · from $38Top of the fleet

Sail Toronto Harbour aboard the historic Tall Ship Kajama, a 1930s three-masted schooner. Allow 30 minutes to board, then spend about 90 minutes on the water, helping raise the sails, hearing sea shanties, and viewing the skyline, Toronto Islands, and CN Tower. Food, drinks, and souvenir photos cost extra.

“Took my kids for my daughter's birthday. The staff was helpful and knowledgeable. The whole trip was lovely and we enjoyed every moment!”

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Tall Ship Silva Sailing Cruise Ft. a Live Musician - Live Music with a Halifax View
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Tall Ship Silva Sailing Cruise Ft. a Live Musician

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, leaving from Halifax’s waterfront for views of the Harbour Bridge, Georges Island, McNab’s Island, Cable Wharf, and downtown. A live musician, onboard bar, and passenger-assisted sail raising keep the trip lively. Bring layers, arrive early, and expect the engine to be used for part of the route.

“The boat and staff were great, but being this was our first experience in Halifax, I would have hoped the entertainer played some East Coast music. However, he only played contemporary music despite the fact that many people would have preferred a decent representation of Halifax.”

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JFarwell Sunset Wine and Cheese Yacht Sailing - From Halifax Waterfront to the Northwest Arm
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JFarwell Sunset Wine and Cheese Yacht Sailing

3.JFarwell Sunset Wine and Cheese Yacht Sailing

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

Spend 2.5 hours aboard J Farwell’s sailing yacht, sampling four Nova Scotia wines with local charcuterie as the boat passes George’s Island, McNabs Island, and the Northwest Arm. Crew members such as Ryan, Finn, Andrew, and Ali share sailing tips, local stories, and wine notes. Blankets are available, and flat shoes are wise.

“Bryan, Simone and Megan were awesome on this sunset tour of the harbor. Outstanding and friendly service, and terrific conversations about Halifax and greater Nova Scotia. Terrific experience. Highly recommend.”

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JFarwell Adventure Yacht Sailing in the Halifax Harbour - Halifax Waterfront from the water
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JFarwell Adventure Yacht Sailing in the Halifax Harbour

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 may invite you to raise the main and jib, assist with tacks, or take the helm. You will see the waterfront and Georges Island, with Nova Scotia beer, wine, and spirits available to buy onboard.

“This is a fun and different activity. I do not go sailing everyday so for me it was fantastic. You see Halifax from a different viewpoint. I enjoyed helping out with some sailing tasks. Ryan the captain knows what he is doing. Great activity with a fantastic crew. I highly recommend this.”

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Halifax Sunset Cruise Aboard the Tall Ship Silva - A 75-minute view of Halifax Harbour
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Halifax Sunset Cruise Aboard the Tall Ship Silva

5.Halifax Sunset Cruise Aboard the Tall Ship Silva

★★★★★★★★★★4.8 · 116 reviews · 1h 30m · from $34Lowest fare aboard

Sail Halifax Harbour at sunset aboard the Tall Ship Silva from Cable Wharf. You’ll pass Georges Island, Maugher Beach, McNabs Island lighthouse, and the Halifax Waterfront, with live music on board and an onboard bar selling drinks. Raising the sails depends on wind and sea conditions.

“Zuber was the best! Great day!! Great driver. Good conversation and very engaging. Gave lots of good information and accommodating. Highly recommend!!!”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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