Windsor eh... if you are looking for some great food, you should check out Little Italy which is located on Erie Street. There are a ton of nice Italian restaurants - some quaint diner-like atmosphere and some classy.
The casino is under renovations right now since it was purchased by Caesar's, but it is still open. I've heard the shows are good.
You could go skating downtown at Charles Clark Square (if you skate).
The Windsor riverfront is a few kilometres long and is landscaped, containing walking paths and sculpture gardens / memorials. This is where you will get the best view of Detroit, including the Joe
Downtown is pretty busy on the weekends because all the American kids come over here to get wasted. I don't party down here any more but if you decide to check out a club, my friend owns Jackrabbit Slim's which is a nice spot. There is a bar for whatever taste you have in scenery, or you could check out one of the strip joints if so inclined.
If you have any specific questions about Windsor, feel free to PM me.