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.

One last weekend to set sail! ⛵️🍂After an incredible season on Toronto Harbour, Kajama’s final weekend of public sailing...
10/02/2026

One last weekend to set sail! ⛵️🍂

After an incredible season on Toronto Harbour, Kajama’s final weekend of public sailing is here. Our last sail of 2026 is Sunday, October 4th — so if you’ve been saying “we need to do Kajama before the season ends”… this is your sign. 👀⚓️

🍹 Drinks onboard
🏙️ Toronto skyline views
⛵️ 90 minutes on the harbour
💥 One last chance to sail Kajama in 2026!

Final day: October 4th — grab your tickets before we dock for the season!

Consider us hooked. 🎣🍷⛵️Good drinks, lake breezes and 90 minutes sailing Toronto Harbour aboard Tall Ship Kajama — that’...
09/27/2026

Consider us hooked. 🎣🍷⛵️

Good drinks, lake breezes and 90 minutes sailing Toronto Harbour aboard Tall Ship Kajama — that’s a pretty good catch. 😉

Our season is almost over! Sail with us Thursday–Sunday through October 4th before Kajama docks for the year. ⚓️

Some of the best moments happen on the dance floor. 💃🕺✨Celebrate, laugh, dance and take in the Toronto waterfront aboard...
09/25/2026

Some of the best moments happen on the dance floor. 💃🕺✨

Celebrate, laugh, dance and take in the Toronto waterfront aboard Obsession III. Whether it’s a milestone birthday, anniversary, corporate event or just an excuse to get everyone together, we’ll provide the view — you bring the people. 🥂🌊

⚓ Private charters available through October 11th!

Ending the season with a bang. 💥⛵️🌅Golden hour hits a little different from the deck of Tall Ship Kajama.Our fall sailin...
09/23/2026

Ending the season with a bang. 💥⛵️🌅

Golden hour hits a little different from the deck of Tall Ship Kajama.

Our fall sailing season is here, with sails Thursday–Sunday through October 4th. There’s still time to grab a drink, take in the Toronto skyline and experience the harbour aboard a historic tall ship. ⚓️🍹

Don’t miss the boat! 😉

Whale hello there! 🐋👋Just popping up to remind you that there’s still time to set sail aboard Kajama before we wrap up a...
09/22/2026

Whale hello there! 🐋👋

Just popping up to remind you that there’s still time to set sail aboard Kajama before we wrap up another season! ⛵️

🍂 Sailing Thursday–Sunday through October 4th
🍹 Fully licensed bar onboard
🌊 90 minutes on Toronto Harbour
🏙️ Waterfront & skyline views

Sea you onboard! ⚓️😉

The season isn’t over just yet. 🌅🥂While our public brunch & dinner cruises have wrapped for the year, Obsession III is s...
09/18/2026

The season isn’t over just yet. 🌅🥂

While our public brunch & dinner cruises have wrapped for the year, Obsession III is still available for private charters through October 11th! ⚓

There’s still time to bring your group aboard for one last celebration on Toronto Harbour — corporate events, birthdays, weddings, celebrations and more.

✨ Your guests. Your event. Your boat.
📅 Private charters available until October 11th

Don’t let the season sail away without you. 🛥️

Fall sailing has officially arrived. 🍂⛵️The sails are still going up, but not for much longer! Tall Ship Kajama is now s...
09/17/2026

Fall sailing has officially arrived. 🍂⛵️

The sails are still going up, but not for much longer! Tall Ship Kajama is now sailing Thursdays through Sundays until October 4th.

Cooler air, fewer crowds, a drink from the bar and Toronto Harbour from the deck — fall might just be one of our favourite times to sail. 🍻🌊

Only a few weekends left — get onboard while you can!

09/07/2026

LAST CALL! 🚨🛥️🎶

Groove U Productions is taking over Obsession III and this is your last chance to get onboard! 🔥

Come ready for a night on the water with music, drinks, dancing and Toronto views as Groove U brings the party to the harbour. 🥂🌃

🎟️ Tickets are available — don’t wait until the boat leaves without you!

Mermaids on the rocks, drinks on deck. 🧜‍♀️🥃🌊Consider this your sign to trade dry land for a little time on the water. G...
09/05/2026

Mermaids on the rocks, drinks on deck. 🧜‍♀️🥃🌊

Consider this your sign to trade dry land for a little time on the water. Grab a drink from the bar, enjoy the views and let Tall Ship Kajama take care of the rest. ⛵️

Good drinks. Great views. Better on a boat.

Golden hour looks better under sail. ⛵️🌅Make your next event one to remember with a private charter aboard Challenge. Yo...
09/04/2026

Golden hour looks better under sail. ⛵️🌅

Make your next event one to remember with a private charter aboard Challenge. Your own boat, your own guest list, and Toronto Harbour as the backdrop. 🥂🌊

Perfect for celebrations, corporate events, weddings or simply getting your favourite people together for a night on the water.

Private charters available.

Address

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

Telephone

+14162606355

Website

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