I'm in Toronto as well. One of my parents is from Cuba who came over at the start of the revolution. Have been to Cuba a few times myself. Alepoplait's story about Coppelia is pretty accurate and typical. Locals have to live through the daily drudgery of a state-controlled totalitarian economy, but tourists are treated like royalty. Being a tourist in Cuba is a double-edged sword, however. You stick out like a sore thumb, which means you'll attract a lot of scam artists, and most establishments will force you to pay inflated prices in CUC (convertible pesos, pegged to the US dollar). I was lucky enough to have a friend that helped me navigate all these things, so I was able to pay in CUP for a lot of things and saved money that way.

You might face some culture shock. Things are just done very differently down there. Canadians and Americans tend to be very demanding and Type A when travelling to the island, but Cubans are much more relaxed and "go with the flow." Schedules for a lot of things are suggestions rather than a standard of practice down there. As someone else here said, there's a learning curve when dealing with merchants. You'll have to haggle with people, even when trying to arrange transportation between towns/cities.

Cuba is probably not the best place to learn Spanish though. The Cuban accent is very difficult to understand for people who don't already have some knowledge of the language. People tend to speak very quickly and not enunciate in the same way that Mexicans and Central Americans do. Have you taken any Spanish courses already? If not, George Brown is a pretty good place to learn and at least get a head-start.

Not a lot of love for Havana here, I see, but I honestly love it. Has lots to see, great nightlife. Santiago would be another place you can go if you want a bigger city vibe.

All that said, Cuba is in my blood so I'm biased. You'll find some of the warmest, friendliest people there. If you do go to Havana, hang out at the Malecon in the evening on any given evening, but especially on the weekend. There's basically a party every night there. And if you get yourself a bottle of rum (pretty cheap there), you'll attract lots of new "friends" haha. Also, if you make a friend that can show you around, the "almendrones" are a good way to get around the city. They're basically shared cabs that take specific routes for very cheap.

Good luck to you and happy travels!