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All listings in Canada

Awesome sailboat rentals in Canada.

5.0
(79 Reviews)

Page 1 of 118 listings

36ft Hunter Sailboat Rental in Vancouver, British Columbia
Sailing in Vancouver · 6 guests

36ft Hunter Sailboat Rental in Vancouver, British Columbia

5.0
Snoozed - Active 02 May 2024
C&C 27 Sailboat for rent on Puget Sound
Sailing in Everett · 6 guests

C&C 27 Sailboat for rent on Puget Sound

5.0
$80hour
Romantic Proposals, Birthday Celebrations & Vacation Experiences
Sailing in Vancouver · 2 guests

Romantic Proposals, Birthday Celebrations & Vacation Experiences

5.0
$276hour
Sailing Trips out of La Conner, Washington
Sailing in Anacortes · 8 guests

Sailing Trips out of La Conner, Washington

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

MAXUM 46' YACHT FOR RENT IN VANCOUVER

5.0
$331hour
Instant Book
Sail the Legendary Wind of Howe Sound on 40' Sailing Yacht Charter
Sailing in Squamish · 10 guests

Sail the Legendary Wind of Howe Sound on 40' Sailing Yacht Charter

5.0
$117person
Shadowfax Cruising Catamaran Charter in Nanaimo, Canada
Sailing in Nanaimo · 12 guests

Shadowfax Cruising Catamaran Charter in Nanaimo, Canada

5.0
$95person
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
$184hour
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
$166-$200hour
Catalina 27 Sailboat Rental in Olga, Washington
Sailing in Anacortes · 6 guests

Catalina 27 Sailboat Rental in Olga, Washington

5.0
$90-$125hour
Cozy, Fast, and Fun Sailboat in Vancouver!
Sailing in Vancouver · 4 guests

Cozy, Fast, and Fun Sailboat in Vancouver!

5.0
Snoozed - Active 02 May 2024
Classic rowboat photoshoot
Sailing in Vancouver · 2 guests

Classic rowboat photoshoot

New
$195hour
40ft Beneteau Oceanis Sailboat Charter in Victoria, British Columbia
Sailing in Cordova Bay · 6 guests

40ft Beneteau Oceanis Sailboat Charter in Victoria, British Columbia

5.0
$74hour
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-$150hour
Sailing and Camping in Gulf Islands of British Columbia
Sailing in British Columbia · 4 guests

Sailing and Camping in Gulf Islands of British Columbia

New
$99hour
Baltic 35 Sailboat for Dock Sailing in Sequim, Washington
Sailing in Sequim · 2 guests

Baltic 35 Sailboat for Dock Sailing in Sequim, Washington

New
$250-$350day
Charter Jeanneau 50 DS Sailing Yacht in English Bay
Sailing in North Vancouver · 10 guests

Charter Jeanneau 50 DS Sailing Yacht in English Bay

New
$368hour
Experience the Wildness of the Great Bear Rainforest from our Spacious Pilothouse Sailboat Classic 39ft Cooper "Seawolf"
Sailing in British Columbia · 4 guests

Experience the Wildness of the Great Bear Rainforest from our Spacious Pilothouse Sailboat Classic 39ft Cooper "Seawolf"

New
$920day

Sailing Reviews in Canada

  1. SH

    Sarah

    36ft Hunter Sailboat Rental in Vancouver, British Columbia

    Jim was a wonderful captain! He was super easy to communicate with him, his boat was spotless and very comfortable, it's docked right downtown, so a great location. For the actual sailing portion, he was able to navigate us through high winds that came through, and we always felt safe & in good hands. We will definitely reach out to Jim again for our next sailing adventure in Vancouver!

  2. DD

    Don

    36ft Hunter Sailboat Rental in Vancouver, British Columbia

    You can't go wrong with Jim. He is a fantastic sailor and a wonderful and nicest guy to hang out with. We had an amazing time and we will go out with Jim again. The boat is excellent and very well taken care of. You need to book at least four hours depending on the wind if you want to get out into the ocean. He let me take the wheel and I had a blast. Our visiting friends from Holland who are serious sailors, also had a great time. We highly recommend Jim and his great sailboat.

  3. TL

    Trevor

    Romantic Proposals, Birthday Celebrations & Vacation Experiences

    My fiancée and I had a wonderful time on our recent voyage! The crew were very friendly and accommodating and even helped us with a last minute schedule change due to weather. We enjoyed learning a bit about sailing and can't wait to see all the photos they took for us!

  4. LP

    Lala

    Romantic Proposals, Birthday Celebrations & Vacation Experiences

    We had the most beautiful day at sea for my boyfriend’s birthday surprise. Every detail was taken care of, and we appreciate all the magic moments the Captain provided throughout this special time. Thank you to the whole team for an unforgettable experience and we will be back again for sure! Lots of love from P&J

  5. Kennedy

    Kennedy

    Romantic Proposals, Birthday Celebrations & Vacation Experiences

    We could not have had a better time on our voyage. The Captain was incredibly friendly, very easygoing, and made the trip so comfortable. He was great at reading when we wanted to be alone just the two of us (it was our wedding anniversary), or when to step in and share some fun info about sailing or help us better enjoy ourselves. He even snapped some gorgeous photos of us, taught us about sailing, kept bringing drinks & snacks and was so accommodating when my husband spilled wine all over my shirt 😂 I already have and will continue to recommend this vessel & captain to everyone I know. They also accommodated a very last minute change of dates, which I could not have been more grateful for. 10/10!

  6. Vince

    Vince

    Romantic Proposals, Birthday Celebrations & Vacation Experiences

    The experience we had sailing was like no other. We had high expectations going into it, and our expectations where exceeded! The captain was super nice and helped us explore Vancouver for the first time. There is no better way to discover Vancouver in my opinion. 10/10 would highly recommend