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.

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.

Your event deserves a view like this. 🌅🥂Take your celebration off land and onto the water with a private charter aboard ...
09/02/2026

Your event deserves a view like this. 🌅🥂

Take your celebration off land and onto the water with a private charter aboard Obsession III. From corporate events and birthdays to weddings, anniversaries and milestone celebrations, make the boat yours and experience Toronto from the lake. 🛥️✨

Your guests. Your event. Your night on the water. Now booking private charters.

Sails up, summer’s not over yet. ⛵️☀️🌊There’s still time to get out on the water aboard Tall Ship Kajama! Grab your crew...
08/31/2026

Sails up, summer’s not over yet. ⛵️☀️🌊

There’s still time to get out on the water aboard Tall Ship Kajama! Grab your crew, grab a drink from the bar and take in 90 minutes of sailing and Toronto Harbour views.

Don’t let summer sail away without you. 😉

A little Tipsy Tides never hurt anybody. 🍸🌊😉Grab a drink from the bar, find your favourite spot on deck and let Toronto ...
08/29/2026

A little Tipsy Tides never hurt anybody. 🍸🌊😉

Grab a drink from the bar, find your favourite spot on deck and let Toronto Harbour do the rest. ⛵️☀️

Good drinks, lake views and 90 minutes aboard Tall Ship Kajama — sounds like a pretty solid summer plan to us.

Cheers from the water! 🥂

Your event. Your guest list. Your boat. ⛵️✨Take your next celebration out on the water aboard Challenge. From birthdays ...
08/29/2026

Your event. Your guest list. Your boat. ⛵️✨

Take your next celebration out on the water aboard Challenge. From birthdays and corporate events to weddings and nights out with your favourite people, there’s nothing quite like having Toronto Harbour to yourselves. 🌊🥂

Private charters available — make the lake yours.

When the sky decides to match the view. 🌅💗Pink skies, calm water and an evening aboard Obsession III — not a bad way to ...
08/26/2026

When the sky decides to match the view. 🌅💗

Pink skies, calm water and an evening aboard Obsession III — not a bad way to spend a summer night in Toronto. 🥂🛥️

Join us on the water for a Brunch or Dinner Cruise, or make the whole boat yours with a private charter.

Some views are just better from the lake. ✨

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.

Address

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

Telephone

+14162606355

Website

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