CANADA
The Canadian classics.
The 14 most popular sailing tours, with what each one actually includes, who runs it, and what you will pay.
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.
“The ship is delightful, the views are spectacular, but the live music made the experience! Jackson is a very talented musician. It was one of the best experiences we have ever had!”
Halifax sunset cruise with a small crew, four Nova Scotia wines, cheese board, and hands-on sailing past George’s Island to Northwest Arm.
“Finn and Paul were fantastic! I cannot recommend more highly. We took this sailing trip on our last night in Nova Scotia and it was the perfect way to end our vacation.”
Wind-powered sail in Halifax Harbour with a hands-on crew, small-group vibes, and views of the Waterfront and Georges Island.
“Just the right amount of people per trip for the right size of the yatch. You may even have a chance to steer the boat!”
Small-group sailing on a 44-foot Beneteau from North Vancouver, with snacks, drinks, and big views of Stanley Park and beyond.
“Fantastic afternoon trip with my parents! Both hosts were kind, knowledgeable, friendly, and made it a perfect family afternoon trip. Public transit accessible - and an adorable cat!”
2-hour Tall Ship Silva cruise in Halifax Harbour with live music, big-sail action, and landmark views from downtown.
“Was a great cruise around Halifax harbour, with excellent entertainment. It was very interesting watching the sails be raised and lowered, and to get a little bit of information about the area. There could have been a bit more explanation of the history, but still really enjoyed it!”
Small-group sailing on Okanagan Lake aboard a 46' yacht. Hands-on instruction, paddleboards, and a swim stop for about 4 hours.
“Great company and conversation. Peaceful get away from the hectic world. Highly recommend this experience.”
A small 19+ moonlight yacht cruise from Halifax Waterfront with starry-sky views, blankets, and a knowledgeable crew. Drinks sold aboard.
“The Captain and first mate were awesome. They were very accommodating for us. It definitely made for a memorable experience for my wife and I.”
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…”
Sail out of Mosquito Creek for 2.5 hours past Stanley Park and English Bay on a 50-foot Jeanneau, with snacks and Frederick.
“The crew was super friendly! The boat was spacious & spotless! What a wonderful experience!!”
4-hour sailing from Sooke on the Strait of Juan de Fuca. Small-group sailing lessons, whale-watching chances, and PFDs included.
“We had a great trip and our Skipper Mitchell was super kind and patient with teaching us how to sail.”
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”
2-hour small-group sailing in Toronto with beanbags and a licensed captain, sailing past the CN Tower on Lake Ontario. From $149.
“The experience amazing. The ride was relaxing and the view was incredible. My family and I will definitely do this again.”
Taste Nova Scotia wines on a private yacht at Halifax sunset, with cheese and harbor stories aboard a 2.5-hour sail along the Northwest Arm.
“We had a wonderful cruise. Enjoyed the small group we were with.”
A 60-minute Toronto Harbour luxury yacht cruise with included Prosecco, skyline views, and photo-ready stops—private, smooth, and easy.
“Attentive, friendly, welcoming crew. Would highly recommend this excursion. Communication was well received by the Yacht Team.”
