Tall Ships Kajama, Challenge & Obsession

Tall Ships Kajama, Challenge & Obsession We own and operate Tall Ships Kajama and Challenge and the Yacht Obsession. All boats are available for public sails and private charters.

Cruise the Toronto harbour with us! An industry leader in Toronto Harbour operating in downtown Toronto. Our fleet consists of The Tall Ship Kajama, Obsession III and Challenge. We sail rain or shine and can accommodate parties of up to 489 people. If you are looking for a Prom, Birthday Party, stag and doe party or a team building activity we can help.

Toronto nights just hit different from the water. 🌙⛵️✨Golden hour fading, city lights coming on, and the CN Tower framed...
08/24/2026

Toronto nights just hit different from the water. 🌙⛵️✨

Golden hour fading, city lights coming on, and the CN Tower framed through the rigging of Tall Ship Kajama. 🏙️

Come see Toronto from a whole different point of view before summer sails away.

08/24/2026

♊️ GEMINIS, THIS ONE’S FOR YOU! 🥂🛥️

It’s Gemini season on the water! Get the crew together and celebrate aboard Obsession III with music, drinks, dancing and Toronto views all night long. 🎶🍹🌃

Whether you’re celebrating a birthday or just coming for the party, get ready for a night of good music, good drinks and even better vibes.

Dock ‘n’ Roll 🤘⚓️⛵Trade the sidewalk for the deck and rock your way around Toronto Harbour aboard the Tall Ship Kajama. ...
08/21/2026

Dock ‘n’ Roll 🤘⚓️⛵

Trade the sidewalk for the deck and rock your way around Toronto Harbour aboard the Tall Ship Kajama. Grab a drink from the bar, take in the skyline and enjoy 90 minutes out on the water. 🍻🌊

Because summer in Toronto just rocks a little harder from the lake. 🎸😎

Your private escape on the Toronto waterfront. ⚓️🌊Nothing but open water ahead aboard Challenge. Whether you’re celebrat...
08/19/2026

Your private escape on the Toronto waterfront. ⚓️🌊

Nothing but open water ahead aboard Challenge. Whether you’re celebrating a birthday, planning a corporate event, or just looking for a different way to bring everyone together, make the boat yours with a private charter.

Good company, cold drinks, lake breezes and Toronto as your backdrop. 🥂☀️

Spotted from the deck of Kajama 👀🛥️ Obsession III is out on the water and there’s still time to get onboard this summer!...
08/18/2026

Spotted from the deck of Kajama 👀🛥️ Obsession III is out on the water and there’s still time to get onboard this summer!

🥂 Our final public Brunch Cruise of the season is August 23 — grab your seats before they’re gone!

Want the whole boat instead? Obsession III is also available for private charters — perfect for celebrations, corporate events, parties and more. 🎉

One boat taking in the view of another. ⚓️💙

There’s just something different about seeing the skyline from the water. Step aboard the Tall Ship Kajama for 90 minute...
08/15/2026

There’s just something different about seeing the skyline from the water. Step aboard the Tall Ship Kajama for 90 minutes of sailing, lake breezes, drinks from the bar, and some of the best views of the city.

Your Toronto summer isn’t complete without a sail. ⚓️

08/15/2026

Virgo season is taking over the water! ♍️🛥️🥂

Groove U Productions is back aboard Obsession III for the Virgo Cruise! Get ready for a night of music, drinks, dancing, Toronto skyline views, and nothing but good vibes on the water. 🎶🍹🌃

Virgo or not, you’re invited to come party. 😉 Grab your crew and get ready for a night on the lake!

Ahoy, Matey! ⚓️⛵Adventure is calling from Toronto Harbour! Step aboard the Tall Ship Kajama and spend your summer cruisi...
08/08/2026

Ahoy, Matey! ⚓️⛵

Adventure is calling from Toronto Harbour! Step aboard the Tall Ship Kajama and spend your summer cruising the waterfront, taking in the skyline, grabbing a drink, and making some memories on the water. 🌊☀️

Views like this are best enjoyed from the water. 🌅🛥️Step aboard Obsession III and trade the city for open water, beautif...
08/05/2026

Views like this are best enjoyed from the water. 🌅🛥️

Step aboard Obsession III and trade the city for open water, beautiful sunsets, and an evening cruising Toronto Harbour. Join us for a Brunch Cruise, Dinner Cruise, or make the boat your own with a Private Charter.

Good food, great company, and views that are hard to beat. 🥂

This could be the view from your next event. 🌅🛥️Make Toronto Harbour your backdrop with a private charter aboard Challen...
08/04/2026

This could be the view from your next event. 🌅🛥️

Make Toronto Harbour your backdrop with a private charter aboard Challenge. From golden-hour cruises to evenings on the water, it’s your own private space to celebrate, connect, and take in the views. Perfect for birthdays, corporate events, celebrations, and group outings.

Address

249 Queen's Quay W Suite 111
Toronto, ON
M5J2N5

Telephone

+14162606355

Website

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