The 15 Best Sailing Trips in Canada

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

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

Join the Tall Ship Silva from Halifax’s waterfront for a two-hour harbor cruise with live acoustic music, views of Georges Island, McNab’s Island, the bridges, and downtown. You may help raise the sails, and musicians such as Gary and Jackson add requests, humor, and songs to the trip.

“Amazing trip. Got there late and we were the only people who had to stand so we just landed against the main mast. After 15 minutes, at least half the people were standing to get the best view. By the end, most were standing because the views were incredible. I thought the music (solo acoustic) would take away from the experience but it was really good. He was quite talented and funny. Half way through they raised the sails and let passengers participate. 100% worth it for us.”

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2.JFarwell Sunset Wine and Cheese Yacht Sailing

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

Set sail from Halifax Waterfront with JFarwell Sailing Tours for a 2.5-hour sunset tasting. Sample sparkling wine, Tidal Bay, rosé, and red wine with local charcuterie while the crew shares sailing tips, Halifax stories, and views toward McNabs Island and the Northwest Arm.

“The crew are friendly and very professional. At all times I felt at ease. The wines were delicious as was the charcuterie selections. This is a small group that you’re in close quarters with for the trip. I appreciated how respectful and helpful they were to all passengers.”

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3.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 small yacht with up to 12 people. Crew members such as Ryan, Jeff, Frankie, Finn, and Margaret invite you to help with sails, tacks, and steering while sharing local stories. Wine, beer, and spirits are available to buy onboard.

“The whole experience was great. The crew was knowledgeable and kind and did a great job. It was a relaxing afternoon.”

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4.Vancouver Sailing Experience on a 50 foot Sailboat

★★★★★★★★★★5.0 · 100 reviews · 2 hours 30 minutes (approx.) · from $112

Join Chris, Michelle, and their crew for about 2.5 hours aboard a well-kept Beneteau sailboat. From Mosquito Creek, you pass Coal Harbour, Stanley Park, and Lions Gate Bridge, then set sail toward English Bay. Snacks, drinks, sailing instruction, and the occasional boat cat make this a personal way to see Vancouver.

“We had a lovely afternoon sail with Chris. Chris was great with sailing teen. A memorable family event.”

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5.Tall Ship Harbor Sailing Cruise with Live Music

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

Spend two hours aboard the three-masted Tall Ship Silva, cruising from downtown Halifax past Georges Island, the waterfront, Historic Properties, and the Northwest Arm. Live performers such as Gary and Tommy provide music, while the crew may invite you to help raise the ship’s large sails when conditions allow.

“Ship is a real beauty. Get there early for choice seats not too close to the live music. Crew were excellent and helped the many kids on board to raise the sails.”

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6.JFarwell Moonlight Yacht Cruise from Halifax Waterfront

★★★★★★★★★★5.0 · 48 reviews · 1 hour 30 minutes (approx.) · from $75

Board at Halifax Waterfront at 9:30 p.m. for a 90-minute, adults-only yacht cruise with up to 12 people. Captain Andrew, Frankie, Ray, Ryan, and other crew members have been praised for friendly hosting and sailing know-how. Expect harbour lights, blankets, drinks for purchase, and a calm evening ride.

“We thoroughly enjoyed our moonlight cruise. Frankie and Finn treated us to to an amazing evening on the water. Frankie the Captain was very professional and gave us an informative tour. Finn the deckhand looked after our every need. We would definitely book with them again.”

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7.Okanagan Lake Sailing Tour from Penticton & Naramata BC

★★★★★★★★★★5.0 · 48 reviews · 4 hours (approx.) · from $187

Join Dan and Robyn aboard Anam Cara, a 46-foot Hunter 460, for four hours on Okanagan Lake. You can take the helm, learn sailing basics, swim, use a paddleboard, or relax with your own snacks and drinks. The tour leaves Naramata Marina at noon and returns there.

“We had an amazing afternoon With Dan and Robyn sailing on Okanagan Lake to celebrate my husbands big birthday ! It was an amazing experience. Dan and Robyn are so knowledgable about every aspect of sailing . My son and brother-in-law had a wonderful opportunity to help sail the boat and they thoroughly enjoyed that experience. If you ever need a deckhand, please let our Daniel know. He said he enjoyed what you taught him yesterday so much. The day was perfect weather-wise and company wise, and we would certainly use them again to treat our guests to a wonderful Okanagan experience.”

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8.Private Kelowna Sailing Cruise on Okanagan Lake

★★★★★★★★★★5.0 · 42 reviews · 2 hours (approx.) · from $123

Join Brad of Holy Doodle Sailing Charters for a private two-hour sail from the Kelowna Yacht Club. You’ll pass Hot Sands Beach, City Park, downtown, waterfront homes, and the Floating Bridge, with time to learn basic sailing and watch for birds and wildlife.

“100% would recommend this experience. It was probably the best thing we did this summer. So calm, peaceful and beautiful. Brad was a super host and just wanted to create a genuine experience.”

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9.4-Hour Sailing Adventure on The Strait of Juan de Fuca

★★★★★★★★★★4.5 · 27 reviews · 4 hours (approx.) · from $134

From Sooke, captain Gord, Dallas, or Mitchell guides you across the Strait of Juan de Fuca in a small sailboat limited to five people. You can take the helm, learn sailing basics, listen for whales, or simply enjoy the coast. Bring snacks and warm layers.

“Outstanding!! Gord was kind, knowledgeable, friendly, and an easy laugh. For those who wanted to, the sailing was very hands on under Gord's thoughtful guidance. We sailed the Strait of Juan de Fuca approaching international waters. Perfect conditions and a fantastic 32' keelboat in excellent shape. Exhilarating!”

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10.2hr Shared Sailing Experience in Toronto

★★★★★★★★★★5.0 · 23 reviews · 2 hours (approx.) · from $149

Spend about two hours aboard a small sailing vessel with a licensed captain and up to 12 people. Sail Toronto Harbour and past the CN Tower, take the helm if you wish, or stretch out on foredeck beanbags with a blanket. The trip returns to 415 Queens Quay W.

“Amazing experience.. Team was so welcoming and incredibly courteous, professional and warm. Everything was well organised. Not to forget, the views were breathtaking.”

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11.JFarwell Private Yacht Wine & Cheese Sunset Sail

★★★★★★★★★★5.0 · 18 reviews · 2 hours 30 minutes (approx.) · from $149

Join J Farwell Sailing Tours from Halifax’s Lower Water Street for a 2.5-hour private yacht sail with Nova Scotia wine, cheese, and sunset views. Your crew may include captains such as Finn or Caleigh and hosts such as Paul or Simone, with time along the waterfront and into the Northwest Arm.

“Ryan and Ali were incredible hosts, the wine and views were fantastic great night on the water highly recommend. Great group”

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12.60-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise!

★★★★★★★★★★5.0 · 17 reviews · 1 hour (approx.) · from $108

Board at 5 Queens Quay W for a private one-hour yacht cruise through Toronto Harbour, past the CN Tower, Rogers Centre, Yacht Club, and Toronto Islands. Captain Paul and crew members such as Pete, Julie, Sam, Nicole, and Bailey have helped make this a polished choice for sunset views, photos, music, and prosecco.

“Great captain and company. Would have liked a little more information about the city as we toured around. Clean, friendly, enjoyable.”

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13.Sailing Yacht Cruise of Toronto Harbor and Islands

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

Join Gone Sailing Adventures for a 2 or 3 hour day or sunset cruise around Toronto Harbor, the Toronto Islands, and Tommy Thompson Park. Captain Howie, JC, or another English-speaking crew member handles the yacht while you relax, learn sailing basics, or take the helm on a private cruise.

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

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14.Sailing Aerial Adventure

★★★★★★★★★★4.5 · 12 reviews · from $48

Spend up to four hours at Voiles en Voiles in Montreal’s Old Port, tackling more than 100 aerial obstacles across several difficulty levels. Your Grand Adventure ticket also covers climbing walls, a collision course, inflatable games, and a classic carousel. Moderate fitness is needed.

“This was really great, the kids loved it, many different pats for all. The oldest ones (parents) went higher we had a great time we really enjoyed it. I strongly suggest it, be ready to have a roller coaster of emotions hahaha, a lot of fun!”

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15.3hr Shared Sailing Adventure

★★★★★★★★★★5.0 · 10 reviews · from $177

Spend three hours on a shared yacht from Toronto’s Queens Quay, cruising the island lagoons, Humber Bay, and Lake Ontario. You need no sailing experience. Take the helm with the licensed crew or relax on the foredeck beanbags while the city, CN Tower, Sugar Beach, and Gibraltar Point Lighthouse pass by.

“By far one of the most incredible experiences I have ever had. Bucket List activity/outing crossed off the list. Crew were the best!”

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