Canada · SAILING

Top 7 Sailing Trips in Canada

7 tours  ·  ★★★★★★★★★★ 4.7 average  ·  from $40

Tall Ship Silva Sailing Cruise Ft. a Live Musician - A Tall Ship With a Relaxed Feel
Boat Tours in Nova Scotia, Cruises & Boat Tours, Nova Scotia Tours, Sailing, Tour Reviews

Tall Ship Silva Sailing Cruise Ft. a Live Musician

1.Tall Ship Silva Sailing Cruise Ft. a Live Musician

★★★★★★★★★★4.0 · 289 reviews · 2 hours (approx.) · from $40Our pick

Review of Halifax’s Tall Ship Silva cruise, with live music, harbor views, sail raising, onboard drinks, practical tips, and honest value advice.

“Not a lot of info about Halifax/harbour. It was a good experience. Staff were friendly. Maybe could have come around more often to ask about drinks etc”

Check availability →Read our full review

JFarwell Sunset Wine and Cheese Yacht Sailing - Meeting at the Halifax waterfront
Boat Tours in Nova Scotia, Cheese, Cruises & Boat Tours, Evening Experiences, Nova Scotia Tours, Sailing, Tour Reviews, Wine Tours, Wine Tours in Nova Scotia

JFarwell Sunset Wine and Cheese Yacht Sailing

2.JFarwell Sunset Wine and Cheese Yacht Sailing

★★★★★★★★★★5.0 · 149 reviews · 2 hours 30 minutes (approx.) · from $150Top rated

Review of Halifax’s sunset wine and cheese yacht sail, with Nova Scotia wines, harbor views, hands-on sailing, pricing, tips, and booking advice.

“The crew were amazing! Simone, Megan and Brandon were a lively bunch, and made the experience fun and enjoyable. We had luck with the weather, and got a gorgeous sunset paired with good wine and charcuterie. Many thanks for such a wonderful experience!”

Check availability →Read our full review

JFarwell Adventure Yacht Sailing in the Halifax Harbour - Sailing past Halifax Harbour sights
Boat Tours in Nova Scotia, Cruises & Boat Tours, Nova Scotia Tours, Sailing, Tour Reviews

JFarwell Adventure Yacht Sailing in the Halifax Harbour

3.JFarwell Adventure Yacht Sailing in the Halifax Harbour

★★★★★★★★★★5.0 · 147 reviews · 1 hour 30 minutes (approx.) · from $82

Sail Halifax Harbour aboard a small yacht, help set the sails, steer the boat, and enjoy Nova Scotia views for 90 memorable minutes.

“Brandon and Margaret were great hosts. Great way to spend a couple hours. Actually met another couple on a boat which led to dinner and drinks . Great way of meeting people”

Check availability →Read our full review

Halifax: Tall Ship Harbor Sailing Cruise with Live Music - Safety Briefing and the First View of Halifax Harbour
Boat Tours in Nova Scotia, Concerts, Cruises & Boat Tours, Nova Scotia Tours, Sailing, Tour Reviews

Halifax: Tall Ship Harbor Sailing Cruise with Live Music

4.Tall Ship Harbor Sailing Cruise with Live Music

★★★★★★★★★★4.5 · 75 reviews · 2 hours · from $42

Review of Halifax’s Tall Ship Silva cruise, with live music, harbor views, sail raising, practical tips, value, and what to expect.

“The Harbor Cruise on The Silva was fabulous !! Very smooth with a great MC/Musician playing along the way. The boat was comfortable and thoughtly enjoyable. The sights along the journey were outstanding. Only advice I can offer is be prepared for full sun for 2 hours !!”

Check availability →Read our full review

Ottawa: Downtown Yacht Cruise - Wed-Sun @ 6PM - 75 Minutes - Meeting the yacht near Pirate Marina
Boat Tours in Ottawa, Cruises & Boat Tours, Ottawa Tours, Sailing, Tour Reviews

Ottawa: Downtown Yacht Cruise – Wed-Sun @ 6PM – 75 Minutes

5.Downtown Yacht Cruise – Wed-Sun @ 6PM – 75 Minutes

★★★★★★★★★★4.4 · 8 reviews · from $90

Review the 75-minute Ottawa yacht cruise for sunset views, a small group, music, onboard drinks, pricing, and practical tips.

“It was a great time. Well priced overall. We were lucky as we had perfect weather and only six of us on the bow. The crew was very attentive and just wanted everyone to enjoy themselves. Definitely recommend at least once.”

Check availability →Read our full review

Halifax: Sunset Wine and Cheese Sailboat Cruise - George’s Island and the First Harbor Views
Boat Tours in Nova Scotia, Cheese, Cruises & Boat Tours, Evening Experiences, Nova Scotia Tours, Sailing, Tour Reviews, Wine Tours, Wine Tours in Nova Scotia

Halifax: Sunset Wine and Cheese Sailboat Cruise

6.Sunset Wine and Cheese Sailboat Cruise

★★★★★★★★★★5.0 · 5 reviews · 2h 30m · from $118

Sail Halifax at sunset with Nova Scotia wines, 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!”

Check availability →Read our full review

Penticton Okanagan Lake: Sailing Tour - Getting comfortable aboard Anam Cara
Cruises & Boat Tours, Sailing, Tour Reviews, Tours

Penticton Okanagan Lake: Sailing Tour

7.Penticton Okanagan Lake: Sailing Tour

★★★★★★★★★★5.0 · 5 reviews · 4 hours · from $182

Spend four hours sailing Okanagan Lake from Naramata, with hands-on instruction, swimming, paddleboarding, and views of the Bench.

“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!”

Check availability →Read our full review

Scroll to Top

Explore Canada

Every kind of Canadian day out, and the best of each.