Challenge Private 2021

Looking for a little outdoor getaway in the city this summer?

On board our tall ship Challenge, we offer a relaxing and safe option for you and your group at Toronto’s Harbourfront with unique and fantastic views of the skyline. View our sailing schedule and charter fees to get started. Food and bar options are the only decisions you’ll need to make- let us take care of the rest.

With government-mandated restrictions put in place for your safety, we have made sure to meet all requirements and are ready to adapt our policies as needed. Challenge is best with intimate group gatherings so that you can get the attention and service you deserve.

We offer 2 &2 ½ hour private functions with up to 6 bubbles on Challenge of between 3- 8 passengers with a maximum 25 guests on board. To learn more about capacity and restrictions click here.


Set sail with Challenge, just steps from downtown Toronto. This 96 foot three-masted schooner is your ultimate exclusive destination ‘on-the-go’, with a sleek appearance and a chic interior – complete with lounge style couches below deck, different food options and a full service bar – Challenge and our crew rise to any occasion with style.

How Do I Book?

Step 1 – Select a date and time for your event. 

Step 2 – Select a food option. A variety of options include choosing one of
our individually packaged gourmet meals, or outside catering by a certified caterer with ready to eat
prepackaged meals, or no food at all. 

Step 3 – Select bar options.

For more information please see our Terms & Conditions page.

For Policy/Covid-19 Procedures, please click here


Since 1991, Great Lakes Schooner Company has been providing first-class yachts for corporate events, weddings, and educational cruises.