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Sailing Georgian Bay

Rated 5.0 out of 5 from 12 reviews.Owen Sound, Canada

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Experience hosted by Hailey

2.5 hours
Includes food, drinks, transportation, equipment
Up to 4 people
Hosted in English

What you'll do

Our private sailing adventure begins in Owen Sound Harbour (25 minutes from Sauble Beach, 40 minutes from the Blue Mountains, 1 hour and 20 minutes from Tobermory, and 2 hours from Toronto Pearson International Airport).

Help us untie the cleats and cast off from the docks. We’ll wave goodbye to the marina lighthouse as we motor through the channel markers, where we will hoist our sails. With both the jib and the main sail raised, we will cut power to the engine. Now, only the sound of the waves lapping against the hull of the boat will interrupt the tranquility of our sunset. Sit back and relax with a glass of wine from Ontario's burgeoning wine country or a can of craft beer from our local brewery.

With ample photo opportunities, Georgian Bay's beauty is unparalleled. We'll encounter windswept pines, majestic towering limestone cliffs, craggy beaches, and crystal-clear turquoise waters, together creating a one-of-a-kind private sailing experience.

But more than just snapping countless iPhone photos, we’ll learn seamanship skills, including reading wind direction and adjusting point of sail, picking up various sailing terminology along the way.

As we make our way back to shore, we'll present a locally sourced charcuterie board complete with artisanal meats and gourmet cheeses to satisfy all cravings!
Our private sailing adventure begins in Owen Sound Harbour (25 minutes from Sauble Beach, 40 minutes from the Blue Mountains, 1 hour and 20 minutes from Tobermory, and 2 hours from Toronto Pearson International Airport).

Help us untie the cleats and cast off from the docks. We’ll wave goodbye to the marina lighthouse as we motor through the channel markers, where we will hoist our sails. With both the jib and the main sail raised, we w…

Hailey's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
Learn more

What's included

  • Food
    Locally Sourced Charcuterie Board (please let your captains know of any foo...
  • Drinks
    Alcoholic Refreshments and Non-Alcoholic Options Alike
  • Transportation
    Pearson 30 Sailboat
  • Equipment
    Approved Life Jackets or PFDs on Board for Each Person, First Aid Kit, Dram...
From $196
/ person

Meet your host, Hailey

Host on Airbnb since 2014
  • 12 Reviews
  • Identity verified
Sails are led by Captains Hailey and Dan!

Hailey is a South Florida transplant who fell in love with the great white north (and Dan!). She is an avid traveller, conservationist, educator, and iPhone photographer. She has scaled the Andes Mountains in Patagonia, sailed across the Gulf Stream to the Abaco Islands, and been deported from Estonia.

Dan grew up sailing Lake Ontario and the Thousand Islands as a Royal Canadian Sea Cadet. He’s an all-around handy guy, with a love for vintage motorcycles, woodworking, and beard maintenance.

Together they live in Owen Sound, where they keep their sailboat, a Pearson 30 named “Windswept.” Follow their sailing adventures on Instagram @sailinggeorgianbay.
Sails are led by Captains Hailey and Dan!

Hailey is a South Florida transplant who fell in love with the great white north (and Dan!). She is an avid traveller, conservationist, educator, and iPhone photographer. She has scaled the Andes Mountains in Patagonia, sailed across the Gulf Stream to the Abaco Islands, and been deported from Estonia.

Dan grew up sailing Lake Ontario and the Thousand Islands as a Royal Canadian Sea Cadet. He’s an all-around handy guy, with a love…
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Where you'll be

Onboard a 30-foot sailboat, we'll cruise the turquoise waters of Georgian Bay via Owen Sound Harbour, a long, narrow, and deep inlet of water cutting between the high cliffs of the 500-million-year-old Niagara Escarpment on either side.

Rated 5.0 out of 5 from 12 reviews.

Jonelle
August 2020
What a wonderful experience! If you have any doubts, just go ahead and book it! You won't regret it! Hailey and Dan were such lovely hosts - they tailored the experience to us and what their guests are comfortable with. We learned a lot about sailing and enjoyed a beautiful sunset while snacking on the charcuterie board. It was a memorable experience that we'll do again in a heart beat!
What a wonderful experience! If you have any doubts, just go ahead and book it! You won't regret it! Hailey and Dan were such lovely hosts - they tailored the experience to us and…
Mackenzie
August 2020
This was an incredible experience. Hailey and Dan were amazing hosts and we had so much fun. We would recommend this to anyone, especially for a girls trip!
Matthew
August 2020
Hailey and Dan were great! They were very personable, comfortable and relaxed, but stayed processional and kept us safe amd entertained. They both had an extensive background in sailing and knew all of the techniques and terms, especially for their age. They provided awesome charcuterie varieties and some local brews, which were also really good! They let us participate in changing direction of the boat and how to tie all of the ropes involved with sailboats, what different parts were, what they do. They both made it seem like it was a boat trip with some friends. They brought us to certain areas around the bay, showed us some cool buildings with some history, shared personal stories and asked us about our lives. Overall a really great experience. Would recommend for a couple looking for a romantic date or a small party to relax on a boat and see some beautiful sunsets.
Hailey and Dan were great! They were very personable, comfortable and relaxed, but stayed processional and kept us safe amd entertained. They both had an extensive background in sa…
Farrah
August 2020
A great time with these two! It was refreshing to see younger people doing cool things like this. Only thing I should tell you is heed to warning to dress warm (even if it is a hot August evening)
Katie
August 2020
Hailey's airbnb sailing experience on Georgian Bay was an excellent experience for the first evening of my sister's bachelorette in Meaford. They views and sunset were spectacular, the cheese and meat board was beyond delicious and our hosts were very friendly & welcoming. We wouldn't have changed a thing about this experience! Looking. forward to the next time we are able to go out!
Hailey's airbnb sailing experience on Georgian Bay was an excellent experience for the first evening of my sister's bachelorette in Meaford. They views and sunset were spectacular…
Stephanie
August 2020
Hailey and Dan were the absolute sweetest! Both were super friendly and very hospitable. I decided to do the experience on my own despite concerns that it might be awkward. It definitely wasn’t. I’ve done a few sailing excursions before but none like this. I got first hand experience learning how to sail the boat. They taught me different terminology and explained the theory behind sailing. Hailey prepared a delicious charcuterie board (with veggies from their personal garden! - amazing) and introduced me to a local wines and cider. They suggested other activities in the area that I could do during my visit, while keeping in mind that I was travelling alone. They pushed me outside my comfort zone to try things I’d never thought I’d try and I really appreciated it. I followed their advice and I’m so glad I did! Every Airbnb experience that Ive ever done, has surpassed my expectations and each one just gets better and better than the previous. Thanks for helping to make my visit in Owen Sound and Tobermory amazing, Hailey and Dan! Hope to meet again soon!😊
Hailey and Dan were the absolute sweetest! Both were super friendly and very hospitable. I decided to do the experience on my own despite concerns that it might be awkward. It defi…

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    Activity advisory

    Expert industry partners
    Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
    Know your comfort level
    Please note outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

    Things to know

    Cancellation policy

    Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

    Guest requirements

    Up to 4 guests ages 19 and up can attend.

    Alcohol

    This experience includes alcohol. Only guests who meet the legal drinking age will be served alcoholic beverages.

    More tips

    If a time or date is not available on the calendar, please inquire and we will do our best to accommodate! Follow our sailing adventures on Instagram at www.instagram.com/sailinggeorgianbay.

    What to bring

    Soft-Soled Shoes With Light Coloured Soles (No Black or Leather Soles, Please)

    Comfortable, Seasonally Approriate Clothing