CANADA SAILING TOURS
Wind, season and head-count decide more about a day afloat than the brochure does. These 15 canada sailing tours are set out with the hours, the price and the swim stops so the choice takes a minute.
Set sail from downtown Toronto aboard the three-masted Tall Ship Kajama, a 1930s schooner. You can help raise the sails, hear sea shanties, watch the crew fire a cannon, and see the Toronto Islands and skyline from Lake Ontario. Food and drinks are available for purchase, but narration about the city is limited.
“Staff was friendly and it was a great experience. Just the right amount of time on the water. Would book it again.”
Board the tall ship Silva on Halifax’s waterfront for a two-hour harbour cruise with live acoustic music, onboard drinks, and views of the Harbour Bridge, Georges Island, McNab’s Island, Cable Wharf, and downtown Halifax. You may also help raise the sails, weather and crew plans permitting.
“This was a lovely experience, beautiful day, not over crowded. And the staff was very helpful with my partner who has limted mobility.”
Spend 2.5 hours aboard J Farwell’s yacht, tasting four Nova Scotia wines with local charcuterie as the crew guides you from Halifax Harbour toward McNabs Island and the Northwest Arm. Captains Ryan, Andrew, Finn, and others share sailing tips, local history, and wine notes. The boat carries blankets and two bathrooms.
“Captain Andrew and Deckhand Ali were incredible. They were friendly, attentive, and knowledgeable in various areas (wines offered, local information, and some Nova Scotia history). The experience was amazing- the views, wine/charcuterie, and overall vibes were spectacular!”
Spend about 90 minutes sailing Halifax Harbour aboard a yacht limited to 12 people. The crew may invite you to raise sails, help with tacks, or take the helm. Look for Georges Island, seals, and porpoises, then relax with Nova Scotia wine, beer, or spirits available for purchase.
“Everything was great, insight of the story behind sailing, with the captain being very knowledgeable of their craft.”
Spend 90 minutes aboard the Tall Ship Silva, sailing from Cable Wharf past Georges Island, Maugher Beach, and McNabs Island lighthouse. You can buy drinks at the onboard bar, listen to live music, and help raise the sails if conditions allow. The cruise ends with views of Halifax’s waterfront glowing in the last light.
“Zuber was the best! Great day!! Great driver. Good conversation and very engaging. Gave lots of good information and accommodating. Highly recommend!!!”
Board the three-masted Tall Ship Silva at Cable Wharf for a two-hour Halifax Harbour cruise. You’ll pass Georges Island, Historic Properties, the waterfront, and the Northwest Arm, with live music from performers such as Gary or Tommy. If weather allows, the crew may invite you to help raise the ship’s huge sails.
“It was a really nice boat trip with great music played by Tommy.”
Join Dan and Robyn aboard the 46-foot Hunter 460 Anam Cara for a four-hour Okanagan Lake sail from Naramata Marina. You can take the helm, help with the sails, swim, paddleboard, or simply relax. The group limit is six, and snacks and drinks are welcome in the onboard cooler.
“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…”
Join Brad of Holy Doodle Sailing Charters for a private two-hour cruise from Kelowna Yacht Club. You’ll sail past Hot Sands Beach, City Park, downtown, the Floating Bridge, and waterfront homes, with time to spot birds and learn basic sailing. The boat suits travelers over 12 who can board comfortably and enjoy a moving vessel.
“Our captain, Brad, was very nice and friendly. The weather was not on our side (cloudy, some rain, no wind!) but he still made it enjoyable and fun!”
Set sail from Halifax at 4 pm for about two hours with J Farwell Sailing Tours. A captain and first mate handle the boat while you enjoy a local cocktail or mocktail, open harbour views, and a small group capped at 12 people.
“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”
Spend about 2.5 hours aboard a private yacht from Halifax’s Lower Water Street, tasting Nova Scotia wines and enjoying cheese as the boat follows the waterfront into the Northwest Arm. Crew members such as Finn, Ryan, Paul, and Caleigh have been praised for sailing skill, local stories, and warm service. The route can be personalized.
Cruise Toronto Harbor and the Toronto Islands aboard a 41-foot sailing yacht with a captain and crew. Choose a shared or private 2 or 3 hour sail, ask to learn the basics, or simply relax on deck. Captains such as JC and Howie have led memorable trips, with longer sails sometimes including a Lake Ontario swim.
“Exceptional Captains and Crew! Best experience we had while in Toronto on a long weekend. Highly recommended!!”
Spend 2.5 hours aboard a sailboat from Halifax with four Nova Scotia wines, a local cheese board, and a guided cruise past George’s Island and down the Northwest Arm. You can help hoist the sails, take the helm, or relax on deck. Recent departures have featured skipper Finn and host Emerson, with wine and local-history details throughout.
“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!”
Join Dan and Robyn aboard Anam Cara, a roomy modern sailboat, for four hours on Okanagan Lake. You can help steer, learn basic sailing, swim in warm water, and use a paddleboard while taking in the Naramata Bench. The small group holds up to six people, with pickup by dinghy from Naramata Marina.
“Es war großartig...wir hatten das Glück, mit Robyn und Dan allein zu sein und daher ganz viel Platz auf dem Segler und exklusive Infos zum Segeln, zur Umgebung etc Es hätte an dem Tag etwas mehr Wind sein dürfen 😉 Auch der Bade- und Stand-Up-Paddle-Stopp war super. Bei 38 Grad im Okanagan-Valley genau das richtige Event. Vielen Dank für den tollen Nachmittag!”
Meet your captain at Ahoy Rentals for a private one-hour sail along Kingston’s historic waterfront. No sailing experience is needed. You can learn the basics, ask questions, or simply enjoy the wind and waves while your captain handles the boat. Andrew is praised for his friendly, informative hosting, and the tour includes safety gear and landmark commentary.
Set sail from Halifax’s waterfront for a relaxed two-hour cruise with a custom local cocktail or mocktail on arrival. You’ll pass George’s Island, Pier 21, and Point Pleasant Park, with time to stretch out on deck or try the helm under the crew’s guidance. Extra drinks and grazing boards can be pre-purchased.
Sunset, snorkel, or the whole boat.
