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Set sail with Challenge, just steps from downtown Toronto. This 96’ three-masted schooner is your ultimate upscale destination ‘on-the-go’; with a sleek appearance and a chic interior – complete with lounge style couches, two large LCD televisions and a full service bar – Challenge rises to any occasion with style.
From corporate events to personal parties, Challenge is designed with you in mind: a top notch sound system, a complimentary DJ, and personalized menu availability. Our chefs use many local, fresh ingredients and our catering staff work with you to ensure your gathering is exquisite and unforgettable.
With the best view in the city, of Toronto’s skyline, Challenge offers a fabulous venue for your next soiree; it boasts authentic hardwood decks for sun-seekers, as well as a stellar dining and lounge area below for all-weather luxury and comfort. Challenge can accommodate up to 72 guests, and is waiting for you in the heart of the Harbourfront.
Our experienced, knowledgeable crew is here to customize your sail to accommodate your needs; whether it is traditional sailing or a lavish entertainment experience; Challenge is unsurpassable.

Capacity for 72 guests.
Two large LCD televisions.
Fully licensed bar.
Transport Canada approved.
Professional DJ service.
Complete catering service.
Barbeque facilities.
3 lounge rooms.
Outside deck for all guests.
Full Awnings for bad weather.
Smoothest ride in Toronto.
Challenge is fully- insured, and licensed by both Canadian Coast Guard and the Liquor License Board of Ontario.
A Brief History of Schooners
Schooners were first developed by Dutchmen in the 16th century, and are characterized by fore-and-aft sails on two or more masts. Fore-and-aft sails are set along the line of the keel, not perpendicular to it.
The first ship actually called a schooner set sail in 1713 from Gloucester, Massachusetts. She was built by Andrew Robinson, who overheard a spectator exclaiming "Oh how she scoons" (scoon being a Scots word meaning to skip or skim over water). Mr. Robinson replied, "A schooner let her be!"
Schooners were more popular in North America than in any other region of the world. Two masted schooners are the most common, but schooners with as many as seven masts have been built. Schooners were popular in occupations that required high speed and windward ability, such as slaving, privateering, blockade running and offshore fishing. At the peak of their popularity in the 1800s, there were over 2000 schooners carrying cargo back and forth across the Great Lakes.
Famous racing schooners include the America, the Atlantic, and the Bluenose.
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