Sailing Trips in Canada
Top 10 Best Canada Sailing Trips
Found 22 Sailing Trips activities in Canada. Sort by Popularity.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

Tall Ship Silva Sailing Cruise Ft. a Live Musician
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Canada
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Exellent266 reviews4.2
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

Toronto Tall Ship Boat Cruise
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Canada
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Exellent659 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

Best of Halifax Harbour Boat Tour
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Canada
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Superb74 reviews4.9
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....
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

Halifax Sunset Cruise Ft. a Live Musician
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Canada
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Superb36 reviews4.7
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Sailing Experience on a 50’ 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

Sailing Experience on a 50’ sailboat
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Canada
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Superb94 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

JFarwell Sunset Wine and Cheese Yacht Sailing
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Canada
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Superb149 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
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

JFarwell Adventure Yacht Sailing in the Halifax Harbour
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Canada
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Superb146 reviews5
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
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

2hr Shared Sailing Experience in Toronto
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Canada
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Superb23 reviews5
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....
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

Halifax Summer Breeze Sail
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Canada
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Superb24 reviews5
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center....
Squamish Afternoon Sailing Experience
Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our certified instructors are dedicated to providing a safe, comfortable, and unforgettable outing. Guests are welcome to be as hands... More

Squamish Afternoon Sailing Experience
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Canada
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Superb24 reviews5
Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our....
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

Private Kelowna Sailing Cruise on Okanagan Lake
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Canada
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Superb42 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
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

Vancouver Sailing Tour - Learn the Ropes
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Canada
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Superb1 review5
Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s s....
Private Tour
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
Private Tour

JFarwell Moonlight Yacht Cruise from Halifax Waterfront
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Canada
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Superb48 reviews4.8
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....
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

4-Hour Sailing Adventure on The Strait of Juan de Fuca
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Canada
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Superb25 reviews4.6
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....
Private Tour
Okanagan Lake Sailing Tour from Penticton & Naramata BC
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More
Private Tour

Okanagan Lake Sailing Tour from Penticton & Naramata BC
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Canada
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Superb48 reviews5
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....
Private Tour
3hr Shared Sailing Adventure
Availablie Daily May-Sep Your sailing experience is a great choice to introduce yourself to the sailing world in a casual, relaxed setting. This trip requires no prior sailing knowledge or experience. You have the option of parti... More
Private Tour

3hr Shared Sailing Adventure
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Canada
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Superb10 reviews5
Availablie Daily May-Sep Your sailing experience is a great choice to introduce yourself to the sai....
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

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
Fireworks Dinner Cruise
See Vancouver’s waterfront sights while you dine on a sunset dinner cruise. This leisurely cruise takes you past the downtown skyline, Canada Place, the North Shore Mountains behind the North Shore, the West Vancouver shoreline ... More
Private Tour

Fireworks Dinner Cruise
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Canada
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Good4 reviews3.5
See Vancouver’s waterfront sights while you dine on a sunset dinner cruise. This leisurely cruise ....
Private Tour
JFarwell Sip & Sail aboard the Reverie
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More
Private Tour

JFarwell Sip & Sail aboard the Reverie
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Canada
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Superb19 reviews5
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....
Private Tour
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
Private Tour

Introduction to Sailing in Saint John, NB
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Canada
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Superb4 reviews5
Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5....
Private Tour