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Group Size (2)
All listings in Canada

Awesome sailboat rentals in Canada.

5.0
(66 Reviews)

Page 1 of 118 listings

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
$274hour
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
$329hour
Instant Book
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
$116person
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
$183hour
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
Classic rowboat photoshoot
Sailing in Vancouver · 2 guests

Classic rowboat photoshoot

New
$194hour
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
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
$73hour
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
$292hour
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

5.0
$365hour
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
$914day

Sailing Reviews in Canada

  1. VB

    Victor

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

    Paul is awesome. Had an amazing day. Super friendly and knowledgeable. Highly recommended!

  2. 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!

  3. 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

  4. 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!

  5. 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

  6. AV

    Andre

    Romantic Proposals, Birthday Celebrations & Vacation Experiences

    The Captain & Crew provided an amazing sailing experience to make my proposal to my fiancé special and memorable. They connected with me promptly to provide suggestions, and options fir the trip and supported me all the way through with the coordinating catering, flowers, photography and capturing the moment. Even learned a bit about sailing. Thank you so much for making this moment in life unforgettable 💍❤️❤️ 👌🙏🙏🙏