The 9 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.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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3.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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4.Downtown Yacht Cruise – Wed-Sun @ 6PM – 75 Minutes

★★★★★★★★★★4.4 · 8 reviews · from $90

Join Ottawa Yacht Tours at 6PM for a 75-minute cruise from Pirate Marina. You’ll pass Parliament, the Rideau Locks, and the Alexandra Bridge aboard a clean, stable yacht limited to 12 people, with music, drinks, a sundeck, and no live narration.

“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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5.Private Luxury Yacht Sightseeing Cruise & Prosecco

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

Spend one hour aboard a private Toronto Yachts vessel with a licensed captain, passing the CN Tower, Toronto Islands, Gibraltar Point Lighthouse, Harbourfront, and Hanlan’s Point. You get interior and exterior seating plus one glass of prosecco, or a soft drink if preferred.

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

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6.Sunset Wine and Cheese Sailboat Cruise

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

Join J Farwell Sailing Tours for a 2.5-hour sunset sail from the Halifax Waterfront. With skipper Finn, host Emerson, or another English-speaking crew team, you can help with the sails, taste four Nova Scotia wines, and cruise past George’s Island toward 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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7.Penticton Okanagan Lake: Sailing Tour

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

Join Robyn and Dan aboard the roomy Anam Cara for a four-hour sail from Naramata Marina. Learn basic sailing, take the helm if you like, then swim or paddleboard in warm Okanagan Lake while enjoying views of the Naramata Bench.

“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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8.Tiki Party Yacht Rental

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

Rent a private Tiki-themed yacht in Kelowna for 2 to 4 hours with up to 15 people. You get life jackets, USB ports, a BBQ, and a bar. No boating license is needed, but fuel, a captain, and a $1,000 damage deposit require extra planning.

“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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9.Skippered Sailing Charter

★★★★★★★★★★4.7 · 4 reviews · 1 hour

Join Captain Andrew and the Ahoy Rentals team for a private one-hour sail from Kingston’s waterfront. Your group of up to five can learn sailing basics, watch historic landmarks from the water, or sit quietly as the wind carries you across clear Lake Ontario waters.

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