Top 13 Sailing Trips in Canada

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

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

Tall Ship Silva sails from Halifax Waterfront for about 2 hours with live commentary, live music, and a chance to help hoist the sails.

“Though the conditions were perfectly fine, this boat spent three quarters of the 2 hours motoring about. When they finally raised the sails, it was only for show because the engines were never turned off and the boat really didn't go sailing. To make matters a little worse, the live music which was selected to "entertain" the guests wasnt nautical and far too loud. We were all glad not to hear it when we got off the boat.”

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2.JFarwell Sunset Wine and Cheese Yacht Sailing

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

A small-group Halifax sunset cruise with guided Nova Scotia wine and cheese, plus hands-on sailing past George’s and McNabs Islands.

“The crew were amazing! Simone, Megan and Brandon were a lively bunch, and made the experience fun and enjoyable. We had luck with the weather, and got a gorgeous sunset paired with good wine and charcuterie. Many thanks for such a wonderful experience!”

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3.JFarwell Adventure Yacht Sailing in the Halifax Harbour

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

A hands-on, wind-powered Halifax Harbour yacht sail with up to 12 guests, sweeping views, helm time, and Georges Island scenery.

“Ryan and Margaret made it spectacular! Made us feel like welcome, gave us a little history of the area.”

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4.Tall Ship Harbor Sailing Cruise with Live Music

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

Sail Halifax Harbour on the Tall Ship Silva, enjoy live music, and if wind cooperates, help raise the sails on this 2-hour cruise.

“It was a really nice boat trip with great music played by Tommy.”

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5.Okanagan Lake Sailing Tour from Penticton & Naramata BC

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

Small-group Okanagan Lake sail from Naramata and Penticton on the Anam Cara. Learn sailing, paddleboard, swim, bring snacks.

“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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6.Private Kelowna Sailing Cruise on Okanagan Lake

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

Private 2-hour sailing cruise from Kelowna Yacht Club on Okanagan Lake, with wildlife spotting and hands-on sailing guidance.

“I had a wonderful boating experience with Brad! I went with my sister and Brad was punctual, friendly, and kind. He made us feel welcome and was very knowledgeable, which made the whole trip smooth and enjoyable. It was such a pleasant experience - we’d love to go again!”

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7.Sailing Yacht Cruise of Toronto Harbor and Islands

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

Cruise Toronto Harbor and the Islands on a 41-foot sailboat, with skyline views, optional sunset timing, and easy, crew-led sailing.

“Another great tour with Captain JC (this time I got the name right). Perfect conditions for a fantastic Sunday afternoon sailing experience. Fastest boat on the lake … 🥳”

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

★★★★★★★★★★4.4 · 8 reviews · from $90

Ottawa River sunset yacht cruise with a small group, no narration, and skyline views of Parliament, the Rideau Locks, and Alexandra Bridge.

“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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9.Private Luxury Yacht Sightseeing Cruise & Prosecco

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

Cruise Toronto Harbour in a private luxury yacht for 1 hour, with prosecco, skyline views, and a fully licensed captain.

“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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10.Sunset Wine and Cheese Sailboat Cruise

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

Sail Halifax’s Northwest Arm at sunset with four Nova Scotia wine pours, cheese pairings, and hands-on sail time.

“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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11.Penticton Okanagan Lake: Sailing Tour

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

Sail Okanagan Lake from Naramata, learn the wind and wheel, then swim and paddleboard with a small, friendly crew for 4 hours.

“A wonderful day out on Lake Okanagan with hosts Dan and Robyn aboard Aman Cara. From stepping into the dingy to going aboard, we were made to feel extremely welcome. My husband (a keen sailor), was able to take the helm and chat to Dan, about his passion for sailing and learn about Aman Cara and about sailing on the lake. We were fortunate that there was a good strong breeze in the afternoon, great sailing weather. Robyn was happy to chat to the rest of her guests, who were happy just to have a day out on the water and learn a little about sailing. We enjoyed a late…”

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12.Tiki Party Yacht Rental

★★★★★★★★★★3.8 · 4 reviews · 2 - 4 hours · from $351

Cruise Kelowna on a Tiki-themed yacht with BBQ and bar onboard. Private rental for up to 15, no license needed, USB ports included.

“We booked a trip for a yacht with 11 guests at 1:00pm. Unfortunately our renter showed up 30-45 minutes late and claimed that he was waiting for us the entire time. We requested for him to accomodate us the lost time since our booking was 2 hours and with setup and taking the boat out, we were close to 1 hour left. The renter informed us that he would let us know and refund us and after multiple attempts have heard nothing back. Aside from all of this, the reason we booked the boat was the bbq and bar. Upon arrival he also informed us that the bbq was out…”

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13.Kingston: Skippered Sailing Charter

★★★★★★★★★★4.7 · 4 reviews · 1 hour · from $117

Private 1-hour skippered sail for up to 5 along Kingston’s waterfront, wind-and-waves views, safety gear, and sailing basics.

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