Bear in mind that your US Credit Cards & debit cards will not work in Cuba so it will have to be a cash vacation. You can exchange cash at the airport for tourist pesos - different value than the pesos the population uses. Do not buy cigars from anybody other than an official store or factory because they will be fakes!
We have been twice & it is refreshing to see - as opposed to the other Caribbean islands. Very poor but no beggars. Very run down but it still functions. Virtually no crime. On our last trip we rented a Vitara jeep & drove to 3 different locations. We really enjoyed it.
See
It's Not Easy (to give away a suitcase filled with drugs) for my trip report from 2006. Lots of pictures too,
There are regular flights to most major Cuban cities from Toronto & Montreal. Air Transat - a cheap junket carrier - really sucks btw.
Ian