Sailing Trips in Canada
Top 10 Best Canada Sailing Trips
Found 26 Sailing Trips activities in Canada. Sort by Popularity.Halifax Sunset Cruise Ft. a Live Musician
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More
Likely to Sell Out Halifax Sunset Cruise Ft. a Live Musician
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Canada
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Superb89 reviews4.6
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Tall Ship Silva Sailing Cruise Ft. a Live Musician
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More
Likely to Sell Out Tall Ship Silva Sailing Cruise Ft. a Live Musician
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Canada
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Exellent355 reviews4.3
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....
Toronto Tall Ship Boat Cruise
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order fr... More
Likely to Sell Out Toronto Tall Ship Boat Cruise
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Canada
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Exellent741 reviews4.3
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Ta....
Best of Halifax Harbour Boat Tour
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More
Likely to Sell Out Best of Halifax Harbour Boat Tour
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Canada
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Superb109 reviews4.9
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....
JFarwell Adventure Yacht Sailing in the Halifax Harbour
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More
Likely to Sell Out JFarwell Adventure Yacht Sailing in the Halifax Harbour
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Canada
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Superb160 reviews5
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
Vancouver Sailing Experience on a 50 Foot Sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More
Likely to Sell Out Vancouver Sailing Experience on a 50 Foot Sailboat
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Canada
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Superb113 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
JFarwell Sunset Wine and Cheese Yacht Sailing
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More
Likely to Sell Out JFarwell Sunset Wine and Cheese Yacht Sailing
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Canada
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Superb173 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
2hr Shared Sailing Experience in Toronto
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More
Likely to Sell Out 2hr Shared Sailing Experience in Toronto
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Canada
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Superb27 reviews5
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....
3hr Discover Sailing Adventure
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager to explore the basics of sailing. Guided by experienced instructors on our specially designed First 22 yacht, you’ll dive into es... More
Likely to Sell Out 3hr Discover Sailing Adventure
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Canada
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Superb16 reviews4.8
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager t....
Halifax Summer Breeze Sail
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's Island, Pier 21, Point Pleasant Park, and more. This laid-back sail is designed for you to en... More
Likely to Sell Out Halifax Summer Breeze Sail
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Canada
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Superb30 reviews5
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center....
JFarwell Moonlight Yacht Cruise from Halifax Waterfront
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More
Likely to Sell Out JFarwell Moonlight Yacht Cruise from Halifax Waterfront
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Canada
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Superb52 reviews4.7
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....
Introduction to Sailing in Saint John, NB
Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5 to 3-hour introduction to boating experience. Led by a certified Sail Canada instructor, this cruise offers first-time boaters a ... More
Likely to Sell Out Introduction to Sailing in Saint John, NB
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Canada
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Superb9 reviews5
Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5....
Private Kelowna Sailing Cruise on Okanagan Lake
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More
Private Tour
Likely to Sell Out Private Kelowna Sailing Cruise on Okanagan Lake
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Canada
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Superb53 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour
Scenic Sailing Experience in Vancouver with Local Captain
Join us for a public sailing tour and experience Vancouver’s coastline aboard a beautifully maintained sailing yacht. Choose between Harbour & Wildlife Sail on Saturdays or Sunset Sail on Thursdays, each offering a relaxed cruis... More
Private Tour
Likely to Sell Out Scenic Sailing Experience in Vancouver with Local Captain
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Canada
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Superb1 review5
Join us for a public sailing tour and experience Vancouver’s coastline aboard a beautifully mainta....
Private Tour
Private Sailing Charters in Halifax Harbour
Explore Halifax Harbour like never before with a private sailing charter designed just for you. Whether you're looking to relax, celebrate a special occasion, or explore the coastline, each tour caters to your group's preferences.... More
Private Tour
Likely to Sell Out Private Sailing Charters in Halifax Harbour
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Canada
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Superb1 review5
Explore Halifax Harbour like never before with a private sailing charter designed just for you. Whet....
Private Tour
4-Hour Sailing Adventure on The Strait of Juan de Fuca
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More
Private Tour
Likely to Sell Out 4-Hour Sailing Adventure on The Strait of Juan de Fuca
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Canada
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Superb28 reviews4.7
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....
Private Tour
Vancouver Sailing Tour - Learn the Ropes
Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience takes you through the picturesque False Creek and English Bay, where you’ll be ... More
Private Tour
Likely to Sell Out Vancouver Sailing Tour - Learn the Ropes
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Canada
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Superb2 reviews5
Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s s....
Private Tour
Sailing Charter around Vancouver Harbour Private Tour
Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and has all the features of a large cruising Yacht with a rare balance betw... More
Private Tour
Likely to Sell Out Sailing Charter around Vancouver Harbour Private Tour
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Canada
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Superb2 reviews5
Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and....
Private Tour
Private Luxury Catamaran Moonlight Party in Halifax
The ultimate private sailing experience! The Reverie is the newest boat in our fleet. The Reverie is the perfect balance of luxury and space to enjoy the atmosphere of the Halifax Harbour under the Moonlight The deck layout has b... More
Private Tour
Likely to Sell Out Private Luxury Catamaran Moonlight Party in Halifax
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Canada
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Superb1 review5
The ultimate private sailing experience! The Reverie is the newest boat in our fleet. The Reverie is....
Private Tour
VIP Luxury Single Floor Yacht Charter for up to 12 Guests
Step aboard our private Single-Floor Yacht and enjoy a one-of-a-kind cruise through Toronto Harbour with breathtaking skyline views. Unlike crowded public tours, this experience offers exclusivity, comfort, and personal service—... More
Private Tour
Likely to Sell Out VIP Luxury Single Floor Yacht Charter for up to 12 Guests
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Canada
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Superb1 review5
Step aboard our private Single-Floor Yacht and enjoy a one-of-a-kind cruise through Toronto Harbour ....
Private Tour