Sailing Trips in Canada: 15 That Use a Whole Day Well

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, leaving from Halifax Waterfront for views of the Harbour Bridge, Cable Wharf, Georges Island, McNab’s Island, and Fort George. A live musician provides the soundtrack, while the crew may invite you to help raise the sails. Drinks and snacks are available for purchase.

“Pleasant time sailing in the Halifax Harbor. The scenery is pretty, the crew was exceptional and the musician was very good.”

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2.JFarwell Sunset Wine and Cheese Yacht Sailing

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

Spend 2.5 hours sailing from Halifax Waterfront past George’s Island and McNabs Island into the Northwest Arm. You’ll taste four Nova Scotia wines with local charcuterie, hear local stories, and may help with the sails. Captains and crew such as Ryan, Finn, Andrew, and Ali are praised for their sailing, wine, and Halifax knowledge.

“What a lovely sunset sail experience. Ryan and Finn were professional and attentive yet so down to earth and knowledgeable with both historical and modern day factoids. Well orchestrated from Start to Finish. Highly recommend!”

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3.JFarwell Adventure Yacht Sailing in the Halifax Harbour

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

Join J Farwell Sailing Tours for a 90-minute, small-group sail from Halifax’s waterfront. Captains such as Ryan, Jeff, and Frankie invite you to raise sails, assist with tacks, and sometimes steer. Enjoy harbour views, local drinks for purchase, and the fun bow-side pancake when the sail swings across.

“There wasn’t much wind for sailing, so we motored around the harbor. But it was a beautiful day and the crew did the best they could under the circumstances.”

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4.Tall Ship Harbor Sailing Cruise with Live Music

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

Sail Halifax Harbour aboard the 130-foot Tall Ship Silva for two hours of waterfront views, live music, commentary, and possible hands-on sail raising. Performers such as Gary and Tommy have entertained past departures. Board at Cable Wharf, arrive 15 minutes early, and bring comfortable shoes.

“The Harbor Cruise on The Silva was fabulous !! Very smooth with a great MC/Musician playing along the way. The boat was comfortable and thoughtly enjoyable. The sights along the journey were outstanding. Only advice I can offer is be prepared for full sun for 2 hours !!”

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5.JFarwell Moonlight Yacht Cruise from Halifax Waterfront

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

Board at 9:30 p.m. on Halifax’s waterfront for a 90-minute, 19+ moonlight cruise with a maximum of 12 people. The crew sets sail when conditions allow, while captains such as Andrew, Frankie, Ray, and Ryan have shared local stories on past departures. Bring a sweater, step onto the bow, and watch the harbour lights from the water.

“Totally wonderful. Excellent staff and exceptional views. A highlight of our NS adventure. Highly recommend.”

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6.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 about four hours on Okanagan Lake. You can learn to steer, help raise the sails, swim, paddleboard, or simply relax with your own food and drinks. The tour starts at noon from Naramata Marina and is listed for a maximum of six people.

“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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7.Private Kelowna Sailing Cruise on Okanagan Lake

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

Join skipper Brad of Holy Doodle Sailing Charters for a private two-hour sail from the Kelowna Yacht Club. You will pass Hot Sands Beach, City Park, downtown Kelowna, the Floating Bridge, and waterfront homes while watching for birds and wildlife. Brad may also let you take the helm, with guidance.

“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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8.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 with Nova Scotia wines, cheese, and sunset views. Your crew may include captains and hosts such as Finn, Ryan, Paul, or Caleigh, who share local waterfront stories while you cruise Halifax Harbour and the Northwest Arm.

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

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9.Toronto: Sailing Yacht Cruise of Toronto Harbor and Islands

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

Board a 41-foot yacht at Gone Sailing Adventures for a 2 or 3-hour day or sunset cruise around Toronto Harbor, the Toronto Islands, and Tommy Thompson Park. Captain JC, Howie, and other English-speaking crew members handle the sailing, or teach you the basics if you want to take the helm. Choose a shared or private outing.

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

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10.Sailing Aerial Adventure

★★★★★★★★★★4.5 · 12 reviews · from $48

At Voiles en Voiles in Montreal’s Old Port, you get up to four hours on aerial obstacle courses for children and adults, a climbing wall, collision course, inflatables, and a classic carousel. Expect a physical outing with different difficulty levels, helpful staff, and pirate-ship scenery. A moderate fitness level 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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11.Downtown Yacht Cruise – Wed-Sun @ 6PM – 75 Minutes

★★★★★★★★★★4.4 · 8 reviews · from $90

Join Ottawa Yacht Tours for a 75-minute, 6 PM cruise from Pirate Marina. You will pass Parliament, the Rideau Locks, and the Alexandra Bridge aboard a licensed yacht for up to 12 people. There is no narration, but there is music, a sundeck, onboard service, a washroom, and time to enjoy drinks as the evening light fades.

“The yacht was clean, beautiful and comfortable and the staff was amazing! 10/10 would recommend and would do it again!”

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12.Toronto: 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, cruising Toronto Harbour past the CN Tower, Harbourfront, Toronto Islands, Hanlan’s Point, and Gibraltar Point Lighthouse. You get exterior and interior seating plus one glass of prosecco or a soft drink. Captain Paul has earned special praise for friendly service.

“Captain Paul and hostess were very nice and made it a fun excursion. Price was quite high for what this experience is-- essentially taking a boat out for 1 hour to take a photo or two. We were given a water bottle. No prosecco available or provided despite this being part of the name of the activity and a major feature on the website for this activity. No partial refund provided when we raised this issue. We had to bring up the prosecco ourselves and were told they had planned not to mention it since it was not available-- not great customer service. Offered 20% off a future booking but…”

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13.Sunset Wine and Cheese Sailboat Cruise

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

Spend 2.5 hours sailing from Halifax with a hosted tasting of four Nova Scotia wines and a local cheese board. You can help hoist the sails, assist with tacks, take the helm, or relax as Finn, Emerson, Ali, or Derek share stories about the wines, waterfront, and Northwest Arm.

“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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14.Penticton Okanagan Lake: Sailing Tour

★★★★★★★★★★5.0 · 5 reviews · 4 hours · from $182

Join Robyn and Dan aboard Anam Cara for a four-hour sail from Naramata Marina. You can take the wheel, learn basic sailing, swim in warm Okanagan Lake, and use the paddleboards. The boat carries up to six people, with shaded seating, a cabin, bathrooms, and room for your own picnic and drinks.

“We had a lovely afternoon with Robyn and Dan! We learned a lot about sailing (with not having to do the work - our choice) and tried out paddle boarding. Truly a way to experience the Penticton / Naramata area from a different perspective. It was like spending an afternoon with friends! Highly recommended!!”

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15.Tiki Party Yacht Rental

★★★★★★★★★★3.8 · 4 reviews · 2 - 4 hours

Rent a private Tiki Party Yacht in Kelowna for 2 to 4 hours with up to 15 people. You get life jackets, USB ports, an onboard bar, and a BBQ, though fuel, a $1,000 damage deposit, and a captain cost extra. No boating license is needed, and the meeting point depends on your booking.

“It was nice and easy going! We had a wonderful time.. the boat had everything we needed!”

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