Canada · SAILING
The 15 sailing trips below are priced, timed and sorted so the choice takes minutes: what each one includes, how far it goes and who it suits.
Review the Tall Ship Silva cruise in Halifax, with live music, harbour views, sail raising, practical tips, pricing, and honest drawbacks.
“This was one of the highlights of our trip. Loading was very easy. The crew were courteous and polite. The views were amazing! Live music was a bonus. Highly recommend this tour!”
Review of Halifax’s JFarwell sunset wine and cheese sail, with Nova Scotia wines, harbor views, crew tips, pricing, and practical advice.
“Brandon & Margaret were absolutely great hosts. Margaret handled the boat like the back of her hand. You could tell she’s passionate about sailing. Brandon was also great, explaining how to adjust the sails, etc. We were served 4 glasses of Nova Scotia wines, but if wine wasn’t your thing you could swap it out for another drink. 2 bathrooms on board & a beautiful experience. There’s no dress code but I’d recommend flat shoes. If you’re worried about getting cold, they have blankets on board to keep you comfortable. If you’re on the fence about booking, don’t be! It’s worth it :)”
Sail Halifax Harbour aboard a small yacht, help handle the sails, spot Georges Island, and enjoy a hands-on Nova Scotia outing.
“I bought this sailing excursion for my dad as a Father’s Day gift him and his fiancé they had the most amazing time. They said the crew was incredibly hospitable. They called to thank us and tell us what a nice day they had. My dad said he would highly recommend to anyone in the area. He even called when he got home to make sure that we left a tip for the crew.”
Sail Vancouver Harbour on a small-group Beneteau with city views, snacks, drinks, sailing lessons, and a possible boat-cat welcome.
“Really awesome experience...loved the whole trip. The host Chirs was really friendly. Felt good throughout.”
Sail Halifax Harbour aboard the 130-foot Tall Ship Silva with live music, city views, sail raising, and a relaxed two-hour cruise.
“Ship is a real beauty. Get there early for choice seats not too close to the live music. Crew were excellent and helped the many kids on board to raise the sails.”
Review of Halifax’s 90-minute moonlight yacht cruise, with harbor views, small-group sailing, drinks, blankets, pricing, and practical tips.
“The moonlight sailing cruise was an exceptional experience for me.It was a nice,cool July evening with a clear sky.It was so beautiful to sail along the waterfront of Halifax harbour,seeing all the patio lights and looking up to the sky where the stars came out and shine.It was a very peaceful atmosphere and very relaxing.The sailing crew with Frankie and Ben did an amazing job in explaining all the important landmarks to know within the Harbour area.I had an amazing time and highly recommend this tour.”
Review of the four-hour Okanagan Lake sailing tour from Naramata, with hands-on sailing, paddleboards, small groups, pricing, and practical tips.
“We had an amazing afternoon With Dan and Robyn sailing on Okanagan Lake to celebrate my husbands big birthday ! It was an amazing experience. Dan and Robyn are so knowledgable about every aspect of sailing . My son and brother-in-law had a wonderful opportunity to help sail the boat and they thoroughly enjoyed that experience. If you ever need a deckhand, please let our Daniel know. He said he enjoyed what you taught him yesterday so much. The day was perfect weather-wise and company wise, and we would certainly use them again to treat our guests to a wonderful Okanagan experience.”
Review the private Kelowna sailing cruise on Okanagan Lake, with practical details on price, views, skipper Brad, timing, and who should book.
“Our 2 hour sailing cruise with Brad was a highlight for our family. We celebrated a 40th birthday on board and Brad was a very competent and gracious guide.”
Review the Vancouver Mosquito Creek sailboat cruise, with Lions Gate views, English Bay sailing, snacks, Fred the boat cat, and practical tips.
“A great day - Chris and Michelle were super welcoming, kind, and friendly and it was a beautiful experience.”
Review of Sooke’s four-hour Juan de Fuca sailing trip, with hands-on lessons, whale-watching chances, pricing, weather tips, and booking advice.
“I had a wonderful time, Gord went above-and-beyond to ensure I had a pleasurable experience and Dallas was and excellent instructor.”
Review of Vancouver’s Granville Island catamaran whale tour, with orcas, humpbacks, naturalist guides, practical tips, and honest value advice.
“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”
Review of Toronto’s 2-hour shared sailing trip, with CN Tower views, small groups, beanbag seating, pricing, tips, and practical details.
“The crew was super kind and the view was amazing. The best part was when we sat sit in front of the boat with comfy blankets, playing our own music with the bluetooth speaker as we watched the sunset - truly unforgettable and a must-do in Toronto. I wish we had a bit more privacy/space though as we were often interrupted to be offered drinks (even though we stated we did not want any) or take photos that we did not really ask for. I told JC who gracefully took the feedback. I would still recommend anyway”
Review of Halifax’s private yacht wine and cheese sunset sail, with route details, value, weather tips, food, crew, and booking advice.
“We had a wonderful cruise. Enjoyed the small group we were with.”
Review of Toronto’s private one-hour luxury yacht cruise, with Prosecco, skyline views, Toronto Islands, sunset tips, pricing, and FAQs.
“We had a great experience. Paul was kind enough to take pictures of our family at different locations and was accommodating throughout.”
Sail Toronto Harbor and the Islands on a 41-foot yacht, with skyline views, helpful crew, sunset options, and a possible Lake Ontario swim.
“Exceptional Captains and Crew! Best experience we had while in Toronto on a long weekend. Highly recommended!!”
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