Canada · SAILING
25 reviewed
Below are the 15 best sailing trips in Canada right now, with what each one costs, how long it runs and the kind of traveller it suits. The first is the safest booking on the page.
A 2-hour Halifax tall ship sailing past the Harbor Bridge, Cable Wharf, and Georges Island, with live music and a chance to hoist sails.
“Wonderful. Loved the singer/ musician with the great voice and song selection. Would highly recommend.”
Halifax sunset yacht sail with four Nova Scotia wines and cheese, plus hands-on sailing in a small group. 2.5 hours.
“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 :)”
Halifax wind-powered yacht sailing with small-group sail handling, bow views, and Nova Scotia wine and spirits available onboard.
“Hands on and small group. Jeff the Skipper excellent. First sailing lesson and it was wonderful. Would do it again.”
Sail on the Wandering Eye from Mosquito Creek, pass Lions Gate Bridge, and cruise Stanley Park and island waters with snacks and drinks included.
“This was the best time I've ever had in Vancouver! Could not have had a better time. The hosts were so friendly and fun, the views are unmatched and the vibe was bliss. Would recommend and will definitely book again!”
2-hour Tall Ship Silva sailing in Halifax Harbour with live music, scenic sights, and a chance to raise the sails. From Cable Wharf.
“It was a really nice boat trip with great music played by Tommy.”
Four-hour sailing on Okanagan Lake in a small group, with hands-on lessons, paddleboards, and swims, starting from Naramata.
“What a day! Our 4-hour sailing excursion with Dan and Robyn was everything we didn’t know we needed. These two are the dream team—friendly, informative, and able to read the vibe better than a seasoned bartender. Want to learn the ropes (literally)? They’ve got you. Prefer to just lounge and pretend you're in a yacht commercial? Also covered. The boat was gorgeous—clean, comfortable, and clearly loved. We laughed, we relaxed, we maybe pretended it was our boat for a hot minute. It was such a fantastic experience, we’re already planning our next “spontaneous” sail. Highly, highly recommend!”
A 90-minute moonlight yacht cruise from Halifax Waterfront with small-group sailing, bow views, blankets, and calm harbor night energy.
“The Captain and Finn were fantastic. Really pleasant and friendly but also incredibly knowledgeable. It was a wonderful and relaxing experience on a gorgeous ship. One of the best things we did on our trip. There was an assortment of drinks and cheese available as well.”
Private 2-hour sailing cruise on Okanagan Lake from Kelowna Yacht Club. Learn the basics, spot wildlife, and glide past downtown sights.
“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!”
Sail Vancouver from Mosquito Creek to English Bay on a 50-ft Jeanneau, with snacks, drinks, and Frederick the boat kitty.
“beautiful boat Interesting and informative crew Weather cool and waves mild AN enjoyable day indeed”
Hands-on 4-hour sailing on Vancouver Island with whale-watching chances, small-group lessons, and a calm captain on the Strait of Juan de Fuca.
“Dallas was an excellent captain. Safety was the primary concern and the comfort and wellbeing for the sailors was a high priority. We maneuvered through the harbor to the Pacific Ocean on the West Coast of Vancouver Island. The winds started out calm but picked up as we went further out. Fog hung over the water in the distance but burned off with the rise in temperature. Dallas was engaging in conversation spanning a diverse range of topics. His demeanor was calm but engaging. We had a great 4 hours on the water enjoying not only the sailing adventure but the beautiful coastline. So an overall A+ for the day!”
Cruise from Granville Island on the semi-covered Jing Yu catamaran for a guided Salish Sea wildlife hunt, with whale sightings guaranteed.
“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”
Small-group 2-hour sailing from Toronto’s Queens Quay past the CN Tower, with beanbags. No experience needed, captain-led.
“Great experience for the first time sailing. I want to come again with my family. I will surely share my experiences with my friends & relatives. If you get a chance to sail, don't miss gone sailing....they are wonderful...captain was an experienced person.”
Taste Nova Scotia wines on a private Halifax yacht at sunset, sail the waterfront into the Northwest Arm, and enjoy wine and cheese.
“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.”
1-hour Prosecco cruise on a luxury yacht from downtown Toronto, passing CN Tower, Rogers Centre, Toronto Islands, and more.
“Great captain and company. Would have liked a little more information about the city as we toured around. Clean, friendly, enjoyable.”
Climb, balance, and zip around Montreal’s Old Port with over 100 aerial obstacles, inflatables, and pirate-ship fun in about 4 hours.
“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”
