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All listings in Canada

Awesome sailboat rentals in Canada.

5.0
(67 Reviews)

Page 1 of 116 listings

Sailing Trips out of La Conner, Washington
Sailing in Anacortes · 8 guests

Sailing Trips out of La Conner, Washington

5.0
$500/day
High Demand
MAXUM 46' YACHT FOR RENT IN VANCOUVER
Events in Vancouver · 12 guests

MAXUM 46' YACHT FOR RENT IN VANCOUVER

5.0
$356/hour
Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 10 guests

Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

5.0
$32/hour
Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building
Sailing in Vancouver · 8 guests

Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

5.0
$178/hour
Charter Jeanneau 50 DS Sailing Yacht in English Bay
Sailing in North Vancouver · 10 guests

Charter Jeanneau 50 DS Sailing Yacht in English Bay

5.0
$356/hour
50ft Searay Yacht - Waterfall Cruise at Deep Cove
Powerboats in Port Moody · 14 guests

50ft Searay Yacht - Waterfall Cruise at Deep Cove

5.0
$428/hour
Limited Availability
Nautical Adventures | 42ft Hunter Passage Sailboat
Sailing in Vancouver · 8 guests

Nautical Adventures | 42ft Hunter Passage Sailboat

5.0
$92/hour
Catalina 27 Sailboat Rental in Olga, Washington
Sailing in Anacortes · 6 guests

Catalina 27 Sailboat Rental in Olga, Washington

5.0
$90+/hour
Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 12 guests

Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC

New
$284/hour
Beneteau 41.1 Oceanis Sailing Charter in Vancouver
Sailing in Vancouver · 6 guests

Beneteau 41.1 Oceanis Sailing Charter in Vancouver

5.0
$356/hour
Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington
Tours in Anacortes · 6 guests

Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

5.0
$200/hour
Luxury 50ft Custom Catamaran in Vancouver for 12 Guests
Sailing in Vancouver · 12 guests

Luxury 50ft Custom Catamaran in Vancouver for 12 Guests

New
$392/hour
Overnight Stay aboard a beautiful 65' Schooner in Lopez Island
Overnight in Lopez Island · 12 guests

Overnight Stay aboard a beautiful 65' Schooner in Lopez Island

New
$50/hour
Santana 22 for up to 4 people in Olga Washington
Sailing in Anacortes · 4 guests

Santana 22 for up to 4 people in Olga Washington

New
$100+/hour
35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands
Sailing in Vancouver · 6 guests

35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

5.0
$114/hour
Instant Book
26' Sailing Boat for Exploring and Camping in Gulf Islands of British Columbia
Sailing in British Columbia · 5 guests

26' Sailing Boat for Exploring and Camping in Gulf Islands of British Columbia

New
$96/hour

Sailing Reviews in Canada

  1. EM

    Erik

    35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

    We had a great trip with James, he was very knowledgeable about the area and suggested several trip options depending on what we were looking to do and how long we wanted to be out. He was great to talk to while sailing and was completely flexible while on the trip. Our son loved getting to sail the boat. If we come back, would definitely look to setup another (maybe longer) trip. Thanks!

  2. PP

    Philip

    35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

    James was a great captain for your family! Was flexible with our itinerary and had some great conversation! Would highly recommend James to anyone looking for a private charter!

  3. Alyssa

    Alyssa

    Sailing Trips out of La Conner, Washington

    Great day sailing! TK is very experienced & knowledgeable. He is a great communicator. The boat is kept in clean condition. Our family enjoyed the trip.

  4. Jess

    Jess

    Sailing Trips out of La Conner, Washington

    The location, sailboat, incredible captain made this trip phenomenal. We made up our own itinerary based on what we needed and the captain ensued that was part of the itinerary. Prior to the trip, the captain promptly answered all our questions, and while sailing was easy going and extremely knowledgeable. Our group had never sailed, however TK (the captain) provided clear guidance and direction completely erasing this concern. We had an incredible time out on the water, sailing for the very first time. Would very much do it again, and know I will rate everyone in the further against the captain (TK). He had great communication, conversation was incredible, and better yet he made you feel comfortable on the boat.

  5. Sherne-marie

    Sherne-marie

    Sailing Trips out of La Conner, Washington

    Terje was an excellent host whose main focus was ensuring the trip was both memorable and magical. i learned so much from this experience and from the captain. we went to the most beautiful spots that made me question if i was in Washington or Tahiti.

  6. SL

    Sarah

    Sailing Trips out of La Conner, Washington

    We has a perfect day on the water to celebrate my mom's life with close family. Captain was so accomodating and made sure we got our full time in even though we had to delay our departure due to one party arriving late. Terje was flexible and respectful of our wishes and made the trip so easy. We thoroughly enjoyed every minute and highly recommend chatering with Terje. Will definitely sail with him again!