Canada · SAILING
Every trip has one free day too few. These 15 sailing trips justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
Review of Halifax’s Tall Ship Silva cruise, with live music, harbor views, sail raising, onboard drinks, practical tips, and honest value advice.
“Not a lot of info about Halifax/harbour. It was a good experience. Staff were friendly. Maybe could have come around more often to ask about drinks etc”
Review of Halifax’s sunset wine and cheese yacht sail, with Nova Scotia wines, harbor views, hands-on sailing, pricing, tips, and booking advice.
“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!”
Sail Halifax Harbour aboard a small yacht, help set the sails, steer the boat, and enjoy Nova Scotia views for 90 memorable minutes.
“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”
Sail Vancouver Harbour aboard a small-group yacht with city views, snacks, drinks, sailing lessons, and friendly local hosts.
“Incredible way to see the harbor and get some fresh air. Chris and Michal are fantastic and personable hosts and worked hard to make sure we were all having a great time. Frederick the cat was a highlight for our animal loving girls”
Review of Halifax’s Tall Ship Silva cruise, with live music, harbor views, sail raising, practical tips, value, and what to expect.
“The Harbor Cruise on The Silva was fabulous !! Very smooth with a great MC/Musician playing along the way. The boat was comfortable and thoughtly enjoyable. The sights along the journey were outstanding. Only advice I can offer is be prepared for full sun for 2 hours !!”
Review of Halifax’s 90-minute moonlight yacht cruise, with waterfront views, small groups, drinks, sailing tips, pricing, and practical advice.
“A very enjoyable evening! Would highly recommend! Halifax at moonlight is delightful! We met some very interesting people. And our tour guides were very informative.☺️”
Review the Okanagan Lake sailing tour from Naramata, with sailing lessons, paddleboards, swim stops, pricing, tips, and practical advice.
“What a experience! So enjoyable, I'll be back - if I can manage to book a spot next year. I booked quite a few excursions in BC but this was my favorite by a long shot. Dan and Robyne were the hosts everyone hopes for. Engaging in sailing lingo when guests inquired and allowing them to man the helm and raise the jenny. What fun! I didn't know what to expect, but it was very comfortable with 9 people aboard the 46 foot vessel and as a non-swimmer I never felt anxious or concerned no matter where I chose to enjoy time on the boat as Dan inquired immediately about…”
Sail Okanagan Lake privately from Kelowna with skipper Brad, wildlife views, local stories, and hands-on sailing in a relaxed two-hour cruise.
“Great cruise out on the lake! Very chill, captain was a fantastic host. Would recommend for anyone coming through Kelowna.”
Learn to sail, steer a keelboat, and watch for whales on a four-hour private or semi-private cruise from Sooke.
“Gord was a great captain. If you are interested in sailing, this is an excellent way to spend the day.”
Sail Toronto Harbour in a small group, take the helm or relax on beanbags, and enjoy CN Tower views with a licensed captain.
“Captain ROB and His Helper ROB were excellent part of this trip!! it was a wonderful afternoon sailing the Ontario Lake with beautiful view of Toronto Skyline.”
Sail Halifax at sunset aboard a private yacht with Nova Scotia wine, cheese, skyline views, and a flexible itinerary.
“We had a wonderful cruise. Enjoyed the small group we were with.”
Review of Toronto’s one-hour luxury yacht cruise with Prosecco, skyline views, Toronto Islands, music, sunset options, and practical booking tips.
“My fiancée and had a wonderful tour. Such a great experience with an incredible view of the Toronto skyline. Captain Paul was extremely nice and took some amazing photos for us!”
Sail Toronto Harbor on a 41-foot yacht, with skyline views, Toronto Islands, friendly crew, and optional Lake Ontario swimming.
“Exceptional Captains and Crew! Best experience we had while in Toronto on a long weekend. Highly recommended!!”
Review of Voiles en Voiles in Montreal, a pirate-themed aerial park with ropes courses, climbing, inflatables, and family-friendly challenges.
“Although the facility itself was impressive, the mostly teenage staff was grumpy and really didn’t make an effort to communicate clearly. Lineups were chaotic as it was fairly unclear which line was for which course. My seven-year-old Read more”
Sail Toronto’s islands for three hours, steer the yacht or relax on beanbags, and enjoy CN Tower, lighthouse, beach, and harbour views.
“By far one of the most incredible experiences I have ever had. Bucket List activity/outing crossed off the list. Crew were the best!”
Every kind of Canadian day out, and the best of each.
