Top Canada Sailing Trips

Best of Halifax Harbour Boat Tour
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.9 (89)
$42.83
$41.83

Halifax Sunset Cruise Ft. a Live Musician
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.7 (64)
$40.06
$39.06

Tall Ship Silva Sailing Cruise Ft. a Live Musician
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.4 (299)
$39.50
$38.50

Halifax Summer Breeze Sail
Special Offer
Special Offer
Halifax, Canada

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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (25)
$92.92
$91.92

The Legendary Canadian Coastal Sail
Likely to Sell Out
Likely to Sell Out
Squamish, Canada

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...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (256)
$98.07
$97.07

JFarwell Sunset Wine and Cheese Yacht Sailing
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (155)
$145.13
$144.13

Vancouver Sailing Experience on a 50 Foot Sailboat
Special Offer
Special Offer
Vancouver, Canada

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...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (105)
$108.90
$107.90

JFarwell Adventure Yacht Sailing in the Halifax Harbour
Special Offer
Special Offer
Halifax, Canada

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...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (149)
$79.86
$78.86

Toronto Tall Ship Boat Cruise
Special Offer
Special Offer
Toronto, Canada

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,...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.4 (636)
$37
$36

Okanagan Lake Sailing Tour from Penticton & Naramata BC
Likely to Sell Out
Likely to Sell Out
Kelowna & Okanagan Valley, Canada

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...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (50)
$163.43
$162.43

4-Hour Sailing Adventure on The Strait of Juan de Fuca
Likely to Sell Out
Likely to Sell Out
Vancouver Island, Canada

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...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.8 (25)
$130.74
$129.74

JFarwell Moonlight Yacht Cruise from Halifax Waterfront
Special Offer
Special Offer
Halifax, Canada

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...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (49)
$72.57
$71.57

JFarwell Sip & Sail aboard the Reverie
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (19)
$837.40
$836.40

JFarwell Private Yacht Wine & Cheese Sunset Sail
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.9 (18)
$145.13
$144.13

Private Kelowna Sailing Cruise on Okanagan Lake
Likely to Sell Out
Likely to Sell Out
Kelowna & Okanagan Valley, Canada

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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (50)
$101.64
$100.64

3hr Discover Sailing Adventure
Likely to Sell Out
Likely to Sell Out
Toronto, Canada

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...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (10)
$195.39
$194.39

Introduction to Sailing in Saint John, NB
Likely to Sell Out
Likely to Sell Out
Saint John, Canada

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...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (8)
$65.36
$64.36

Private Luxury Catamaran Moonlight Party in Halifax
Likely to Sell Out
Likely to Sell Out
Halifax, Canada

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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (1)
$944.27
$943.27

2hr Shared Sailing Experience in Toronto
Special Offer
Special Offer
Toronto, Canada

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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (24)
$144.55
$143.55

3.5 hour Sailing Adventure in Nanoose Bay
Special Offer
Special Offer
Vancouver Island, Canada

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
5.0 (3)
$104.60
$103.60

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