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Chances "R" Sailing

Cruises in Barrie
on Lake Simcoe and Kempenfelt Bay

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Captain of Chances

Welcome Aboard in Kempenfelt Bay

Your Captain Phil Pilgrim/Marketing & Sails Director will make sure that you enjoy Lake Simcoe and beyond with the perfect sailing excursion!

Come join us for a fun time—we’ll be so glad to have you aboard.


5-Star Reviews

Family on Chances
Relaxing Ride

Captain Phil took us on a relaxing tour. Sailing was a new experience for our group so we learned a lot. The boat was perfect. Overall one of the highlights of our trip.

– TripAdvisor
Friends on Chances
Relaxing and Informative

We had excellent experience on this 38' Hunter sailboat. The weather cooperated and was just right for being lazy on a quiet sailboat. Captain Phill was extremely friendly and easy to talk to, he has some great stories. We will definitely book another trip with him next time ee are in the Barrie area!

– TripAdvisor
Family on Chances
Scenic Sailing Experience

This was my first time in Barrie and I was surprised at how beautiful the water was. The boat is very spacious and Phil took care of everything. Very enjoyable ride and the weather was perfect! Will definitely be back.

– TripAdvisor
Couple on Chances
A great sailboat ride to see Barrie from Lake Simcoe

I enjoyed the boat ride so much! I had a blast! It was my first sailboat ride. If. Go to the front of the boat... You should hold on and enjoy it! The Captain was extremely nice! Im so glad my gf booked this little gem in barrie!!

– TripAdvisor
Women on Chances
Great experience!

I was fortunate to receive a birthday gift (great idea) for a cruise with Captain Phil. Chances R is a beautiful, comfortable and well maintained boat which Phil handles with ease and confidence. Even when we were sailing at a good clip we all (children included) felt safe and comfortable...Highly recommended and good value.

– TripAdvisor