So it's safe to be Canadian, non-Spanish speaking and wander Havana? I've heard conflicting opinions of this over the years.
I never felt unsafe at any time. If anything, being Canadian is an advantage, as Cuba and Canada have had generally good relations and Canadians make a lot of contributions to the Cuban economy. Keep in mind too that while Canadian tourists around the world often get treated badly when they are mistaken for Americans, there are almost no Americans in Cuba so this is not an issue.
Not being able to speak any Spanish will put you at a disadvantage, as restaurants may not have any English-speaking staff. The cheaper the hotel is, the less likely they will speak English at the reception.
We were often out late and wandering the streets in the dark. A friend of mine just returned from Havana yesterday and talked about wandering around alone, late, running into a group of men on the street and when they realized he was a tourist, they took him home where he hung out with them and had a lovely time.
I'm not sure what you've heard, but keep in mind that American propaganda views dominate our media.
There is some crime, but it is still probably the safest place to go in the Caribbean.
The food in the hotels is what sucked, we never went out to sample the local fare. It was a truly miserable, boring and unremarkable week
Sounds like it! What a shame.
My boss is a social worker, and has been conducting tours of Havana's social services for about 10 years. We also did a bus tour of western and central Cuba a few years ago, and are about to do a tour of eastern Cuba in February. It's all about meeting the people, seeing how they do things (especially since their money and resources are so limited), and getting away from the standard tourist fare. We also have good (and incredibly knowledgeable) friends who act as tour guides, so we get the inside story on a lot of things.
There's so much we can learn from Cuba. If you go back, you really have to wander around and take a good look. It's been mentioned on this forum more than once that walking around is the best way to really get to know another city/country/culture.