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.

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.

Golden hour, but make it Kajama. 🌅⛵There’s nothing quite like watching the sun set over the Toronto skyline from the wat...
08/03/2026

Golden hour, but make it Kajama. 🌅⛵

There’s nothing quite like watching the sun set over the Toronto skyline from the water. Grab a drink, find your favourite spot on deck, and enjoy 90 minutes sailing through Toronto Harbour aboard the Tall Ship Kajama.

This is what summer in Toronto is all about. ☀️🍹

The All White Cruise is back aboard Obsession III! 🤍🛥️Join Groove U Productions on Sunday, August 2 for an evening on th...
08/01/2026

The All White Cruise is back aboard Obsession III! 🤍🛥️

Join Groove U Productions on Sunday, August 2 for an evening on the Toronto waterfront featuring dinner, music, and plenty of dancing.

🤍 All White Cruise 2
📅 Sunday, August 2, 2026
⏰ 7:30 PM – 11:00 PM
🍽️ Dinner included
🎶 Soca, R&B, Reggae & Afrobeats
📍 Aboard Obsession III

Tickets and event details are available through the event organizers on Eventbrite.

Seas the day and make some waves aboard the Tall Ship Kajama! ⛵🌊Sunshine, lake breezes, Toronto views, and a little adve...
07/31/2026

Seas the day and make some waves aboard the Tall Ship Kajama! ⛵🌊

Sunshine, lake breezes, Toronto views, and a little adventure — what better way to spend a summer day?

Step aboard Kajama and experience Toronto Harbour from the water this summer.

Your own private sail. Your own Toronto experience. ⛵🌅Set sail aboard Challenge for a private cruise through Toronto Har...
07/28/2026

Your own private sail. Your own Toronto experience. ⛵🌅

Set sail aboard Challenge for a private cruise through Toronto Harbour, surrounded by incredible waterfront and skyline views.

Perfect for corporate events, birthdays, celebrations, group outings, and special occasions, Challenge gives you and your guests the boat to yourselves for an unforgettable day or evening on the water.

Make your next event a little less ordinary.

Cruise the harbour aboard Obsession III and enjoy the city from a whole new perspective! Whether you’re joining us for a...
07/27/2026

Cruise the harbour aboard Obsession III and enjoy the city from a whole new perspective! Whether you’re joining us for a Brunch Cruise, Dinner Cruise, or your own Private Charter, there’s a perfect way to get out on the water this summer.

🥂 Brunch Cruises
🍽️ Dinner & Dancing Cruises
🎉 Private Charters for corporate events, celebrations & more

Make the Toronto waterfront part of your summer plans!

96 years young and still making waves. 🎂⛵🥂Today we’re celebrating Kajama’s 96th birthday! Since 1930, our legendary lady...
07/26/2026

96 years young and still making waves. 🎂⛵🥂

Today we’re celebrating Kajama’s 96th birthday! Since 1930, our legendary lady has spent nearly a century on the water — and we think that deserves a toast.

Join us aboard today, July 26, grab a drink from the bar, raise a glass to Kajama, and help us celebrate 96 incredible years of history, adventure, and memories on the water.

Here’s to 96 years, Kajama — and many more! ⚓️💛

One of our favorite annual events is back! 🤍⚓Join Groove U Productions aboard Obsession III for the All White Cruise 2 f...
07/26/2026

One of our favorite annual events is back! 🤍⚓
Join Groove U Productions aboard Obsession III for the All White Cruise 2 featuring great music, dinner, and an unforgettable evening on Toronto Harbour.
Tickets available through the event organizer.

Address

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

Telephone

+14162606355

Website

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