Sailing

CANADA

15 Best Sailing Tours In Canada

The Canadian classics.

The 15 most popular sailing tours, with what each one actually includes, who runs it, and what you will pay.

15 Best Sailing Tours In Canada

Tall Ship Silva Sailing Cruise Ft. a Live Musician

Tall Ship Silva Sailing Cruise Ft. a Live Musician - Price and value: what $40.89 buys you on the water

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

Most Popular★ 4.0

Sail the Tall Ship Silva on Halifax Harbour in about 2 hours, with live music, big waterfront views, and a chance to help hoist 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…”

289 reviews2 hours (approx.)From $40.89by Murphys Sailing Tours Ltd

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JFarwell Sunset Wine and Cheese Yacht Sailing

JFarwell Sunset Wine and Cheese Yacht Sailing - Halifax Harbour Views: George’s Island and McNabs Island

2.JFarwell Sunset Wine and Cheese Yacht Sailing

★ 5.0

Halifax sunset cruise with a small crew, four Nova Scotia wines, cheese board, and hands-on sailing past George’s Island to Northwest Arm.

“Truly the best time. It was my dad's 75th birthday, and the captain and crew went out of their way to make sure it was a memorable evening. Excellent sail, excellent service and a great way to see Halifax. A must do.”

149 reviews2 hours 30 minutes (approx.)From $150.21by J Farwell Sailing Tours

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JFarwell Adventure Yacht Sailing in the Halifax Harbour

JFarwell Adventure Yacht Sailing in the Halifax Harbour - Stop 2: Sailing Past Halifax and Getting Involved With Tacks

Vancouver Sailing Experience on a 50 foot Sailboat

Vancouver Sailing Experience on a 50 foot Sailboat - Stanley Park From the Seawall Side: Why This Coast Hits Different

4.Vancouver Sailing Experience on a 50 foot Sailboat

★ 5.0

Small-group sailing on a 44-foot Beneteau from North Vancouver, with snacks, drinks, and big views of Stanley Park and beyond.

“Fantastic day on the water. Great way to see Vancouver from the water. Our hosts were so gracious and knowledgeable and their cat, Fredrick was a fun addition to the crew! This is a must do for anyone visiting Vancouver!”

100 reviews2 hours 30 minutes (approx.)From $112.66

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Halifax: Tall Ship Harbor Sailing Cruise with Live Music

Halifax: Tall Ship Harbor Sailing Cruise with Live Music - Getting started at Cable Wharf (1751 Lower Water St) and finding your best seats

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

JFarwell Moonlight Yacht Cruise from Halifax Waterfront - Meeting at 1599 Lower Water St: Quick Start, Easy Come-and-Go

6.JFarwell Moonlight Yacht Cruise from Halifax Waterfront

★ 5.0

A small 19+ moonlight yacht cruise from Halifax Waterfront with starry-sky views, blankets, and a knowledgeable crew. Drinks sold aboard.

“It can be chilly at night. Bring a sweater. They do provide light blankets on board. Some music or narration would have been nice. I was a little worried when a guest was allowed to drive the boat given that he was drinking. He drove too fast for my liking and made an erratic sharp…”

48 reviews1 hour 30 minutes (approx.)From $75.06by J Farwell Sailing Tours

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Okanagan Lake Sailing Tour from Penticton & Naramata BC

Okanagan Lake Sailing Tour from Penticton & Naramata BC - Dan and Robyn’s Helm Lessons (Even If You’ve Never Sailed)

7.Okanagan Lake Sailing Tour from Penticton & Naramata BC

★ 5.0

Small-group sailing on Okanagan Lake aboard a 46' yacht. Hands-on instruction, paddleboards, and a swim stop for about 4 hours.

“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…”

48 reviews4 hours (approx.)From $187.65by Winds of Change Experiences

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Private Kelowna Sailing Cruise on Okanagan Lake

Private Kelowna Sailing Cruise on Okanagan Lake - Hot Sands Beach to the Floating Bridge: what you’ll actually see while sailing

8.Private Kelowna Sailing Cruise on Okanagan Lake

★ 5.0

Private 2-hour sailing on Okanagan Lake from Kelowna Yacht Club with wildlife spotting, skipper tips, and a personalized cruise.

“Brad was terrific. The weather on the day of our original booking was questionable, so he reached out to give us some other options. We ended up going two days later and had a wonderful time. He’s very knowledgeable about the area and gave us a terrific suggestion for dinner (Block One). Strongly recommend this…”

42 reviews2 hours (approx.)From $123.85by Holy Doodle Sailing Charters

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Vancouver: Mosquito Creek and English Bay Sailboat Cruise

Vancouver: Mosquito Creek and English Bay Sailboat Cruise - From Coal Harbour to Lions Gate Bridge: the scenic warm-up

4-Hour Sailing Adventure on The Strait of Juan de Fuca

4-Hour Sailing Adventure on The Strait of Juan de Fuca - 6585 Goodmere Rd in Sooke: the meeting point and why the right harbor matters

10.4-Hour Sailing Adventure on The Strait of Juan de Fuca

★ 4.5

4-hour sailing from Sooke on the Strait of Juan de Fuca. Small-group sailing lessons, whale-watching chances, and PFDs included.

“Our entire family had an exceptional time! It was the ideal gift for my husband‘s birthday! Gord was incredible at coaching us any giving instructions on how to sail. Neither of us had ever sailed before and we had an exceptional time! I highly recommend this tour for anyone remotely interested in sailing. Gord was…”

27 reviews4 hours (approx.)From $134.88by Starlight Sailing Adventures

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Vancouver: Catamaran Whale Watching Tour, Granville Island

Vancouver: Catamaran Whale Watching Tour, Granville Island - Key things you’ll notice right away

11.Vancouver: Catamaran Whale Watching Tour, Granville Island

★ 4.9

Semi-covered Jing Yu catamaran whale watching from Granville Island, guided by a naturalist. Look for orcas, humpbacks, dolphins.

“We enjoyed the whale watching from Granville island with captain Kevin and guide Marcos. We saw orcas and humpbacks in fairly close proximity. The trip lasted about 5 hours and it was just great! Marcos was very informative and passionate about the animals”

27 reviews5 hoursFrom $165by Wild whales eco tours

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2hr Shared Sailing Experience in Toronto

2hr Shared Sailing Experience in Toronto - Small-Group Sailing Means Better Views and Less Stress

12.2hr Shared Sailing Experience in Toronto

★ 5.0

2-hour small-group sailing in Toronto with beanbags and a licensed captain, sailing past the CN Tower on Lake Ontario. From $149.

“The crew was super kind and the view was amazing. The best part was when we sat sit in front of the boat with comfy blankets, playing our own music with the bluetooth speaker as we watched the sunset - truly unforgettable and a must-do in Toronto. I wish we had a bit more privacy/space…”

23 reviews2 hours (approx.)From $149.11by Gone Sailing Adventures

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JFarwell Private Yacht Wine & Cheese Sunset Sail

JFarwell Private Yacht Wine & Cheese Sunset Sail - What you taste: Nova Scotia wines with cheese and charcuterie

60-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise!

60-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise! - Prosecco on Board: Included Drinks and the 19+ Rule

14.60-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise!

★ 5.0

A 60-minute Toronto Harbour luxury yacht cruise with included Prosecco, skyline views, and photo-ready stops—private, smooth, and easy.

“Our 1 hour tour was fantastic. Our driver Paul was great and the photo opportunities he suggested for us were wonderful, with the Toronto skyline in the background.”

17 reviews1 hour (approx.)From $108.65by Toronto Yachts

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Sailing Aerial Adventure

Sailing Aerial Adventure - Climbing walls and aerial obstacle courses: challenge levels that fit families

15.Sailing Aerial Adventure

★ 4.5

Aerial obstacle courses, zip lines, inflatables, and a climbing wall in Montreal’s Old Port. Grand Adventure lasts up to 4 hours.

“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!”

12 reviewsFrom $48.24by Voiles en Voiles

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