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Top Canada Sailing Trips

22 Results
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 …More

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 minutes Free Cancellation
5.0 (171)
from
$146
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 …More

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 minutes Free Cancellation
5.0 (159)
from
$80
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 …More

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 hour Free Cancellation
4.9 (113)
from
$43
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 …More

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 minutes Free Cancellation
5.0 (111)
from
$115
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 …More

Likely to Sell Out
Likely to Sell Out
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 minutes Free Cancellation
4.8 (51)
from
$73
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 …More

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 hours Free Cancellation
5.0 (51)
from
$183
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 …More

Likely to Sell Out
Likely to Sell Out
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 hours Free Cancellation
5.0 (30)
from
$94
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 …More

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 hours Free Cancellation
4.8 (26)
from
$132
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 …More

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 hours Free Cancellation
5.0 (24)
from
$146
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 …More

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 minutes Free Cancellation
5.0 (19)
from
$844
JFarwell Private Yacht Wine & Cheese Sunset Sail

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 …More

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 minutes Free Cancellation
4.9 (18)
from
$146
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 …More

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 minutes Free Cancellation
5.0 (9)
from
$73
3.5 hour Sailing Adventure in Nanoose Bay

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 …More

Likely to Sell Out
Likely to Sell Out
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 minutes Free Cancellation
5.0 (6)
from
$146
St. Margarets Bay Sailing and Island Anchoring Adventure

Set sail on a 3-hour journey through the stunning St. Margarets Bay, blending sailing excitement with the beauty of Nova Scotia’s coastline. Departing from Shining …More

Likely to Sell Out
Likely to Sell Out

Set sail on a 3-hour journey through the stunning St. Margarets Bay, blending sailing excitement with the beauty of Nova Scotia’s coastline. Departing from Shining...

3 hours Free Cancellation
5.0 (4)
from
$164
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 …More

Vancouver, Canada

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...

6 hours Free Cancellation
5.0 (2)
from
$2,342
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 …More

Vancouver, Canada

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...

3 hours Free Cancellation
5.0 (2)
from
$121
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 …More

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 hours Free Cancellation
5.0 (1)
from
$951
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 …More

Halifax, Canada

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...

2 hours Free Cancellation
5.0 (1)
from
$585
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, …More

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 hours Free Cancellation
4.4 (668)
from
$37
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 …More

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 hours Free Cancellation
4.4 (337)
from
$47

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