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

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.”

Check availability →Read our full review

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!”

Check availability →Read our full review

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.”

Check availability →Read our full review

4.Vancouver Sailing Experience on a 50 foot Sailboat

★★★★★★★★★★5.0 · 100 reviews · 2 hours 30 minutes (approx.) · from $112

Small-group sail from North Vancouver to Stanley Park, Lions Gate, and the islands, with snacks, drinks, and hands-on sailing.

“Great hosts; experienced on the sea Would recommend to others. Loved Frederick the cat - great entertainer”

Check availability →Read our full review

5.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.”

Check availability →Read our full review

6.JFarwell Moonlight Yacht Cruise from Halifax Waterfront

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

9:30 pm moonlight yacht cruise from Halifax Waterfront, small group, blankets, drinks for purchase, 1.5 hours, $75.06.

“Beautiful time on the water with incredible staff leading the way. An unforgettable experience. Book it now!!!”

Check availability →Read our full review

7.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.”

Check availability →Read our full review

8.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!”

Check availability →Read our full review

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

★★★★★★★★★★4.5 · 27 reviews · 4 hours (approx.) · from $134

Learn to sail in the Strait of Juan de Fuca from Sooke. Hands-on helm time, whale-watching vibes, PFDs included.

“Most memorable parts was getting to steer the sailboat and enjoy the water. Not much wind and not seeing much wildlife was a bummer. No whales. Rain was miserable. Very small boat. Doesn’t look like picture.”

Check availability →Read our full review

10.2hr Shared Sailing Experience in Toronto

★★★★★★★★★★5.0 · 23 reviews · 2 hours (approx.) · from $149

A relaxed 2-hour shared sail on Lake Ontario from Toronto, with small-group views of the CN Tower, beanbags, and a helm option.

“There were awesome views of the water and skyline. JC and Donna were the crew, these folks made you feel like family that you like to share time with. I cannot say anything negative, the whole experience was enjoyable and worth the money.”

Check availability →Read our full review

11.JFarwell Private Yacht Wine & Cheese Sunset Sail

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

Sail Halifax at sunset on a private yacht with Nova Scotia wine and cheese, plus harbour stories as you cruise the Northwest Arm.

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

Check availability →Read our full review

12.60-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise!

★★★★★★★★★★5.0 · 17 reviews · 1 hour (approx.) · from $108

1-hour luxury yacht cruise in Toronto Harbour with Prosecco, skyline views, and Toronto Islands. Private group with captain-led fun.

“I was so happy with my boat tour, the captain was so great and provided everything we asked for 😊🥳”

Check availability →Read our full review

13.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 … 🥳”

Check availability →Read our full review

14.Sailing Aerial Adventure

★★★★★★★★★★4.5 · 12 reviews · from $48

Voiles en Voiles in Montreal’s Old Port is a 4-hour family aerial adventure with pirate-themed obstacle routes, inflatables, and a climbing wall.

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

Check availability →Read our full review

15.3hr Shared Sailing Adventure

★★★★★★★★★★5.0 · 10 reviews · from $177

3-hour shared sailing on Lake Ontario from Toronto, cruising island lagoons and landmarks, with beanbags onboard and a chance to steer.

“By far one of the most incredible experiences I have ever had. Bucket List activity/outing crossed off the list. Crew were the best!”

Check availability →Read our full review