7 Canada Sailing Trips Worth Booking

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

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

Spend about two hours aboard the tall ship Silva, sailing from Halifax Waterfront past the Harbour Bridge, Georges Island, McNab’s Island, and Cable Wharf. Enjoy live acoustic music, help raise the sails when conditions allow, and buy drinks from the onboard bar. Gary and other musicians may take requests.

“Great live music, friendly and helpful staff, free coffee, and enjoyable route through the harbour. A good way to spend the afternoon with family.”

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2.3-Hour Whale Watching Expedition

★★★★★★★★★★4.4 · 177 reviews · 3 hours · from $130

Set out from downtown Victoria on a stable 40-passenger catamaran with veteran captains and certified naturalists. Over three hours, you may see orcas, humpbacks, seals, sea lions, otters, and marine birds while guides such as Sophie, Gord, Mike, or Andre explain the Salish Sea.

“We were extraordinarily lucky to find a dozen or more humpback whales in one spot and two that swam within feet of the boat. Amazing views of these magnificent animals. Aside from the huge slice of luck, the boat was comfortable, well staffed and not overcrowded. All staff on board were very friendly and imparted their knowledge well.”

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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 J Farwell’s yacht with a small group, tasting four Nova Scotia wines while sailing from Halifax Harbour toward McNabs Island and the Northwest Arm. Crew members such as Ryan, Finn, Andrew, and Ali add local history, sailing tips, and wine guidance as the evening unfolds.

“Sharing stories about boating and local history and properties. Loved the calm waters and knowledgeable staff !”

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4.JFarwell Adventure Yacht Sailing in the Halifax Harbour

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

Join JFarwell Sailing Tours at 1655 Lower Water St for a 90-minute Halifax Harbour sail aboard a yacht limited to 12 people. Crew members such as Ryan, Jeff, Frankie, Finn, and Margaret invite you to help with sails, try the helm, and enjoy views toward Georges Island. Drinks are available for purchase.

“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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5.Tall Ship Harbor Sailing Cruise with Live Music

★★★★★★★★★★4.5 · 75 reviews · 2 hours · from $42

Step aboard the three-masted Tall Ship Silva at Halifax’s Cable Wharf for a two-hour harbor cruise with live music, commentary, and views of Georges Island, Historic Properties, the waterfront, and the Northwest Arm. If conditions allow, you can help raise the sails.

“Gary, the performer and guide, was very knowledgeable, witty and an incredible performer! It was a great way for my best friend and I to recover from the night before at the Lower Deck.”

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6.Sailing Yacht Cruise of Toronto Harbor and Islands

★★★★★★★★★★4.7 · 12 reviews · 2 - 3 hours · from $138

Set out from Gone Sailing Adventures on a shared or private 2 or 3 hour sail with an English-speaking captain and crew. Cruise past the Toronto Islands and Tommy Thompson Park, learn basic sailing if you wish, or relax on deck. Sunset departures and occasional lake swims add extra appeal.

“Exceptional Captains and Crew! Best experience we had while in Toronto on a long weekend. Highly recommended!!”

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7.Downtown Yacht Cruise – Wed-Sun @ 6PM – 75 Minutes

★★★★★★★★★★4.4 · 8 reviews · from $90

Spend 75 minutes aboard a stable yacht with up to 12 people, cruising from Pirate Marina at 6PM. Expect music instead of narration, views of Parliament, the Rideau Locks, and Alexandra Bridge, plus drinks, a washroom, a sundeck, and a friendly crew.

“It was a great time. Well priced overall. We were lucky as we had perfect weather and only six of us on the bow. The crew was very attentive and just wanted everyone to enjoy themselves. Definitely recommend at least once.”

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