Sailing Georgian Bay
Check local COVID-19 restrictions before booking
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!
Other things to note
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.
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!
Other things to note
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.
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…
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.
- 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.
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…
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…
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.
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…
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…
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…
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…
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.
What to bring
Soft-Soled Shoes With Light Coloured Soles (No Black or Leather Soles, Please)
Comfortable, Seasonally Approriate Clothing
Comfortable, Seasonally Approriate Clothing