The 15 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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5.Halifax Sunset Cruise Aboard the Tall Ship Silva

★★★★★★★★★★4.8 · 116 reviews · 1h 30m · from $34Best value

Spend 90 minutes aboard Halifax’s Tall Ship Silva as the sun drops over the harbour. You’ll pass Georges Island, Maugher Beach, McNabs Island lighthouse, and the waterfront skyline, with live music on board. The crew may invite you to help raise the sails when conditions allow. Drinks are available for purchase at the bar.

“exactly as promised. a tall sailing ship that cruises the Harbour unfurling its sails and catching sundown. the music and merry involvement of passengers made it very enjoyable too”

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6.Tall Ship Harbor Sailing Cruise with Live Music

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

Set out from Halifax’s Cable Wharf aboard the three-masted Tall Ship Silva for a two-hour harbor cruise with live music, commentary, and views of Georges Island, Historic Properties, the waterfront, and the Northwest Arm. You may help raise the sails when conditions allow. Performers have included Gary, Garry, Tommy, and Keith.

“More narrative of area. Maybe some halifax explosion facts among other things. Music was awesome Great sail”

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7.JFarwell Moonlight Yacht Cruise from Halifax Waterfront

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

Set out from Halifax Waterfront at 9:30 p.m. for a 90-minute 19+ moonlight cruise aboard a small sailing yacht. The crew may include captains such as Andrew, Frankie, Ray, or Ryan, with stories, harbor views, music, drinks for purchase, and blankets when the evening turns cool. The boat returns to the same waterfront dock.

“A very enjoyable evening! Would highly recommend! Halifax at moonlight is delightful! We met some very interesting people. And our tour guides were very informative.☺️”

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8.Okanagan Lake Sailing Tour from Penticton & Naramata BC

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

Spend about four hours aboard Anam Cara, a 46-foot Hunter 460, sailing from Naramata Marina with Dan and Robyn. You can learn the helm, help with the sails, swim, use the paddleboards, or relax with your own food and drinks. The group is capped at six, and no sailing experience is needed.

“My son and son-in-law had a spectacular day….thanks Dan and Robyn….by all accounts… you were great hosts…..Cheers Charles.”

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9.Private Kelowna Sailing Cruise on Okanagan Lake

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

Spend about two hours aboard a private sailboat with skipper Brad of Holy Doodle Sailing Charters. From Kelowna Yacht Club, you’ll pass Hot Sands Beach, City Park, downtown, the floating bridge, and waterfront homes. Brad offers sailing instruction, local insight, and a calm, personal outing for guests aged 12 and older.

“Brad and Lori were so informative and welcoming! From our first encounter, we knew this was going to be an enjoyable experience! We learned a lot about the area and chatted like old friends!”

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10.JFarwell Private Yacht Wine & Cheese Sunset Sail

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

Set out from 1599 Lower Water Street for a 2.5-hour private yacht sail along Halifax’s waterfront and into the Northwest Arm. You’ll taste Nova Scotia wines, enjoy cheese and charcuterie, and watch the skyline change in the evening light. Crew members such as Finn, Ryan, Paul, and Caleigh have been praised for sailing skill, local stories, and friendly service.

“We had a wonderful cruise. Enjoyed the small group we were with.”

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11.Sailing Yacht Cruise of Toronto Harbor and Islands

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

Board a 41-foot sailing yacht at Gone Sailing Adventures for a 2 or 3-hour Toronto Harbor cruise. Captain JC, Howie, Aden, or another English-speaking crew member may handle the sailing, teach you the basics, or let you take the helm. Choose shared or private sailing, open-air or covered seating, and a possible swim stop on longer trips.

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

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12.Sailing Aerial Adventure

★★★★★★★★★★4.5 · 12 reviews · from $48

At Voiles en Voiles in Montreal’s Old Port, your Grand Adventure ticket covers up to four hours of aerial courses for children and adults, a climbing wall, collision course, inflatable games, and a classic carousel. Expect a physical, height-based outing with routes for beginners and stronger climbers.

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

★★★★★★★★★★4.4 · 8 reviews · from $90

Spend 75 minutes on a sleek Ottawa Yacht Tours boat, leaving Pirate Marina at 6 PM from Wednesday through Sunday. With up to 12 people aboard, you’ll pass Parliament, the Rideau Locks, and Alexandra Bridge while music fills the yacht. There is no narration, so this suits you if you want sunset views, drinks, and an easy social evening rather than a traditional sightseeing tour.

“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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14.Private Luxury Yacht Sightseeing Cruise & Prosecco

★★★★★★★★★★4.6 · 8 reviews · 1 hour · from $109

Spend an hour aboard a private luxury yacht with a licensed captain, taking in the CN Tower, Toronto Islands, Hanlan’s Point, Sugar Beach, and Gibraltar Point Lighthouse. You’ll get interior and exterior seating, one glass of prosecco or a soft drink, and a quiet harbor route from 5 Queens Quay West.

“thank you Paul for an amazing night you made for us ❤️❤️”

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15.Sunset Wine and Cheese Sailboat Cruise

★★★★★★★★★★5.0 · 5 reviews · 2h 30m · from $118

Spend 2.5 hours aboard a sailboat with a hosted tasting of four Nova Scotia wines and a local cheese board. You can help hoist the sails, assist with tacks, or take the helm while guides such as Finn, Emerson, Ali, and Derek share stories about local wine and Halifax’s waterfront. The cruise ends with sunset near Dingle Tower.

“This event was truly excellent. The boat was spotless and comfortable, our skipper Finn and host Emerson were very knowledgeable and fun. I wouldn’t hesitate to recommend this event to others. Well worth the money!”

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