We went on Tallship Kajama on Friday (24/6) with friends and it was okay. Definitely not worth the full price. We paid 18$ per person as we used the groupon.
We boarded at 7:30 pm. The cruising time was from 8:00-9:30 pm. It got chilly in the night, so carry a windcheater or jacket if you take the evening cruise.
The total sail time is 90 mins. They have beer, wine and mixed drinks onboard and you could order the food too. Drinks were priced okay, as would expect to pay more while on water.
We ordered fries, they were priced at 7$ which was too much. Our order took about 45 mins to arrive and the fries were way too salty and luke warm.
If you have a groupon and want to have a relaxing time, then yes go for it. It's not a lot of fun. And it's not informative as well. They don't tell you about sailing or Toronto or history, so not very appealing for tourists as well.
They take pictures at the start and you could purchase them for 16 bucks. That doesn't seems like a viable business model as the pictures they take is before the start of the trip with nothing interesting in the background plus the photographers are not good, everyone has a decent camera on their phone these days and they can very well take better pictures themselves with a better background. So people will buy those pictures, if the picture was clicked well and had undergone post-processing.
It would be better if you let people take pictures themselves, upload them on facebook with #tallshipkajama and you offer them free printouts(don't cost much), but will give you free advertising on social media.