Top 15 Sailing Trips in Canada

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

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

Sail Halifax Harbour aboard the tall ship Silva with live music, harbour views, a chance to raise the sails, and a full bar on deck.

“The boat and staff were great, but being this was our first experience in Halifax, I would have hoped the entertainer played some East Coast music. However, he only played contemporary music despite the fact that many people would have preferred a decent representation of Halifax.”

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2.JFarwell Sunset Wine and Cheese Yacht Sailing

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

Sail Halifax Harbour at sunset with four Nova Scotia wines, local cheese, and a small crew aboard the JFarwell yacht.

“Ryan the captain and Mitch his first mate were excellent. The experience from beginning to end was exceptional. If you go to Halifax, I urge you to book this trip.”

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3.JFarwell Adventure Yacht Sailing in the Halifax Harbour

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

Sail Halifax Harbour aboard a small yacht, help raise the sails, take the helm, and enjoy views toward Georges Island.

“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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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 with live music, landmark views, and a chance to help raise the sails.

“What a beautiful time on the water. Garry, was an amazing entertainer. We really enjoyed our time on the water. Everyone was so friendly. I was pleasantly surprised of the bathrooms. They were clean and well maintained. I would recommend as a great way to see Halifax.”

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5.JFarwell Moonlight Yacht Cruise from Halifax Waterfront

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

Cruise Halifax Harbour after dark on a small 19+ yacht, with skyline views, drinks for purchase, blankets, and a relaxed 90-minute sail.

“It was the perfect way to celebrate your wedding anniversary. Is was so great and lovely from start to finish!”

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6.Okanagan Lake Sailing Tour from Penticton & Naramata BC

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

Sail Okanagan Lake from Naramata on a 46-foot yacht with hands-on instruction, paddleboards, swimming, and a relaxed four-hour outing.

“What a day! Our 4-hour sailing excursion with Dan and Robyn was everything we didn’t know we needed. These two are the dream team—friendly, informative, and able to read the vibe better than a seasoned bartender. Want to learn the ropes (literally)? They’ve got you. Prefer to just lounge and pretend you're in a yacht commercial? Also covered. The boat was gorgeous—clean, comfortable, and clearly loved. We laughed, we relaxed, we maybe pretended it was our boat for a hot minute. It was such a fantastic experience, we’re already planning our next “spontaneous” sail. Highly, highly recommend!”

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7.Private Kelowna Sailing Cruise on Okanagan Lake

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

Sail Okanagan Lake from Kelowna with skipper Brad, local stories, wildlife views, and a hands-on private cruise for a calm two-hour outing.

“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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8.JFarwell Private Yacht Wine & Cheese Sunset Sail

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

Sail Halifax’s coastline at sunset with Nova Scotia wine, cheese, skyline views, and a flexible private-yacht experience.

“Cullen and Finn - these two lads made the voyage amazing - not just for us - but all 12 passengers. Great stories, great energy, great skill - I mean the sailboat was incredible and so was the wine and cheese - but any brand would be lucky to have two young pros like this representing there brand on Land & Sea.”

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9.Sailing Yacht Cruise of Toronto Harbor and Islands

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

Sail Toronto Harbor and the Islands aboard a 41-foot yacht, with skyline views, fresh air, optional swimming, and a choice of day or sunset cruises.

“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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10.Sailing Aerial Adventure

★★★★★★★★★★4.5 · 12 reviews · from $48

Review of Voiles en Voiles in Montreal, a four-hour pirate-themed aerial park with rope courses, climbing, inflatables, and family-friendly thrills.

“Fun experience. For all ages. Nice trails for beginners and advanced. Also the wall is excellent for kids.”

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

★★★★★★★★★★4.4 · 8 reviews · from $90

Cruise Ottawa’s river at sunset on a sleek 12-person yacht with music, drinks, Parliament views, and a relaxed 75-minute evening ride.

“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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12.Private Luxury Yacht Sightseeing Cruise & Prosecco

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

Cruise Toronto Harbour on a private luxury yacht with prosecco, skyline views, Toronto Islands, and Gibraltar Point Lighthouse.

“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

Sail Halifax at sunset with four Nova Scotia wines, local cheese, hands-on sailing, and views of George's Island and 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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14.Penticton Okanagan Lake: Sailing Tour

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

Spend four hours sailing Okanagan Lake from Naramata, with hands-on instruction, swimming, paddleboarding, and views of the Naramata Bench.

“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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15.Tiki Party Yacht Rental

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

Review the Kelowna Tiki Party Yacht, with BBQ, bar, USB ports, private groups, pricing, fuel costs, and booking tips.

“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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