CANADA
The 15 best canada sailing tours you can book right now, with the price a head, how long each one runs and whether the sails go up. Number one is first for a reason.
Review of Toronto’s Tall Ship Kajama cruise, with skyline views, sail raising, sea shanties, food, timing, value, and practical tips.
“It was good and the only thing that could be improved would making the trip longer. I would limit the volume on purchasing booze. The whole boat knew their life stories of 2 girls and 2 guys”
Sail Halifax Harbour aboard the tall ship Silva with live music, waterfront views, and a chance to help raise the sails.
“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.”
Review of Halifax’s JFarwell sunset wine and cheese sail, with Nova Scotia wines, harbour views, practical tips, pricing, and honest drawbacks.
“Ryan, Ben, & Avery made the experience a highlight of our stay with not only their sailing expertise, but knowledge of history and wine!!”
Sail Halifax Harbour aboard a small yacht, help set the sails, steer the boat, and enjoy Nova Scotia views with a friendly crew.
“This is a fun and different activity. I do not go sailing everyday so for me it was fantastic. You see Halifax from a different viewpoint. I enjoyed helping out with some sailing tasks. Ryan the captain knows what he is doing. Great activity with a fantastic crew. I highly recommend this.”
Cruise Halifax Harbour aboard the Tall Ship Silva at sunset, with city views, live music, sails, and an onboard bar.
“A great evening with friends on the Silva cruising around Halifax harbour. Near the end of the season, so got a bit cool, as to be expected for late September, when the sun went down. Great entertainment from a very talented young singer/songwriter.”
Sail Halifax Harbour aboard the 130-foot Tall Ship Silva with live music, landmark views, and a chance to help raise the sails.
“Loved the music - Gary see you at Madison Square Garden one day. Very fun show. Snacks, drinks, a fun scavenger hunt with certificates signed by the captain. Lovely tour - fun to see the sails raised.”
Review of the Okanagan Lake sailing tour from Naramata, with hands-on sailing, paddleboards, swimming, pricing, tips, and practical details.
“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…”
Review of Holy Doodle’s private Kelowna sailing cruise, with Okanagan Lake views, local wildlife, skipper-led sailing, and practical tips.
“Great experience! Brad is an avid sailor and provides interesting information about the Kelowna area. Also— he was excellent at communicating with us regarding the details of our excursion prior to departure. We had an opportunity to visit with Brad and his lovely wife, Lori, following our sailing—which made the experience that much more memorable.”
Review the Halifax Summer Breeze Sail, a relaxed two-hour cruise with local drinks, harbor views, a small group, and flexible cancellation.
“It was really lovely. The Captain & 1st Mate were friendly & engaging. A bit of history of the harbour area thrown in , & an overall great experience”
Review of Halifax’s private yacht wine and cheese sunset sail, with Nova Scotia wine, skyline views, pricing, itinerary, and booking tips.
“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.”
Sail Toronto Harbor and the Islands aboard a 41-foot yacht, with skyline views, helpful crew, sunset options, and a possible lake swim.
“Exceptional Captains and Crew! Best experience we had while in Toronto on a long weekend. Highly recommended!!”
Sail Halifax at sunset with Nova Scotia wine, local cheese, hands-on sailing, George’s Island, and views of 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!”
Review of a four-hour Okanagan Lake sailing tour from Naramata, with sailing lessons, swimming, paddleboards, and Naramata Bench views.
“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!!”
Sail Kingston’s historic waterfront on a private one-hour charter with an experienced captain, clear water views, sailing basics, and flexible booking.
Relax on a two-hour Halifax sailing tour with a local cocktail, waterfront views, and optional hands-on time at the helm.
Pick a rig, a coast or an afternoon.
