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Top Canada Sailing Trips

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21 Results
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  • Sea to Sky Afternoon Sail
    Likely to Sell Out

    Sea to Sky Afternoon Sail

    191

    Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    US$132.07
    Details
    from
    US$132.07
    Details
  • JFarwell Adventure Yacht Sailing in the Halifax Harbour

    JFarwell Adventure Yacht Sailing in the Halifax Harbour

    121

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    US$81.16
    Details
    from
    US$81.16
    Details
  • Sailing Experience on a 50’ sailboat
    Likely to Sell Out

    Sailing Experience on a 50’ sailboat

    64

    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...
    Read More

     2 hours 30 minutes  Free Cancellation
    from
    US$110.68
    Details
    from
    US$110.68
    Details
  • JFarwell Sunset Wine and Cheese Yacht Sailing

    JFarwell Sunset Wine and Cheese Yacht Sailing

    113

    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...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    US$147.57
    Details
    from
    US$147.57
    Details
  • Toronto Tall Ship Boat Cruise

    Toronto Tall Ship Boat Cruise

    507

    This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    US$31.68
    Details
    from
    US$31.68
    Details
  • JFarwell Best of Halifax Harbour Tour
    Likely to Sell Out

    JFarwell Best of Halifax Harbour Tour

    45

    This 45' sailing yacht is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the sailing...
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     1 hour  Free Cancellation  Instant Confirmation
    from
    US$43.53
    Details
    from
    US$43.53
    Details
  • JFarwell Moonlight Yacht Cruise from Halifax Waterfront
    Likely to Sell Out

    JFarwell Moonlight Yacht Cruise from Halifax Waterfront

    36

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    US$73.78
    Details
    from
    US$73.78
    Details
  • JFarwell Luxury Catamaran Sail from Downtown Halifax
    Likely to Sell Out

    JFarwell Luxury Catamaran Sail from Downtown Halifax

    18

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    US$851.47
    Details
    from
    US$851.47
    Details
  • 4-Hour Sailing Adventure on The Strait of Juan de Fuca

    4-Hour Sailing Adventure on The Strait of Juan de Fuca

    18

    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...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    US$110.68
    Details
    from
    US$110.68
    Details
  • Sailing Adventure on Okanagan Lake from Penticton & Naramata BC

    Sailing Adventure on Okanagan Lake from Penticton & Naramata BC

    43

    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...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    US$184.46
    Details
    from
    US$184.46
    Details
  • Tall Ship Silva Sailing Cruise

    Tall Ship Silva Sailing Cruise

    185

    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...
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     2 hours  Free Cancellation
    from
    US$44.02
    Details
    from
    US$44.02
    Details
  • Halifax Summer Breeze Sail
    Likely to Sell Out

    Halifax Summer Breeze Sail

    11

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    US$94.44
    Details
    from
    US$94.44
    Details
  • Sailing Charter around Vancouver Harbour Private Tour
    Likely to Sell Out

    Sailing Charter around Vancouver Harbour Private Tour

    1

    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...
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     6 hours  Free Cancellation  Instant Confirmation
    from
    US$2,361.10
    Details
    from
    US$2,361.10
    Details
  • Private Kelowna Sailing Cruise on Okanagan Lake

    Private Kelowna Sailing Cruise on Okanagan Lake

    31

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    US$121.74
    Details
    from
    US$121.74
    Details
  • 2hr Shared Sailing Experience in Toronto

    2hr Shared Sailing Experience in Toronto

    17

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    US$139.45
    Details
    from
    US$139.45
    Details
  • JFarwell Private Yacht Wine & Cheese Sunset Sail

    JFarwell Private Yacht Wine & Cheese Sunset Sail

    14

    This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    US$147.57
    Details
    from
    US$147.57
    Details
  • 3hr Shared Sailing Adventure

    3hr Shared Sailing Adventure

    8

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    US$176.34
    Details
    from
    US$176.34
    Details
  • Golden Hour Silva Cruise from Halifax Harbor

    Golden Hour Silva Cruise from Halifax Harbor

    2

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    US$34.73
    Details
    from
    US$34.73
    Details
  • Come experience a Private Sail in Sidney BC Canada
    Likely to Sell Out

    Come experience a Private Sail in Sidney BC Canada

    New To The Site!

    We provide a memorable 3 hour sailing adventure, on our safe, comfortable Hunter 35.5 yacht, which may include possible sightings of orca whales, eagles, seals,...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    US$103.30
    Details
    from
    US$103.30
    Details
  • Fireworks Dinner Cruise

    Fireworks Dinner Cruise

    New To The Site!

    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...
    Read More

     3 hours
    from
    US$221.35
    Details
    from
    US$221.35
    Details
  • Private Luxury Catamaran Moonlight Party in Halifax

    Private Luxury Catamaran Moonlight Party in Halifax

    New To The Site!

    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...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    US$649.30
    Details
    from
    US$649.30
    Details
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Canada Sailing Trips?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Canada Sailing Trips are:

Q: What are the best kid-friendly options for Canada Sailing Trips Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Canada Sailing Trips are:

View all kid-friendly Tours →

Q: Which Canada Sailing Trips have Instant Confirmation?

A: Canada Sailing Trips with Instant Confirmation include:

View all Tours with Instant Confirmation →

Q: Which Canada Sailing Trips have Free Cancellation?

A: Canada Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

Q: Got any more Canada trip ideas?

A: We sure do. Check out our curated lists of hand-picked Canada Tours.

View all Canada Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Canada?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Canada are:

View all tour styles in Canada →

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Lowest Price Guarantee

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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