The one great thing about Cuban Communism, as opposed to Chinese Communism (Cultural Revolution), is that the government has never supressed the arts. Cuban art and music is very colorful, and very pervasive in Cuban society. People are constantly dancing in the streets, in public squares and in restaurants and clubs. The combination of Spanish and African influences have created rich blends of music like rumba, son and mambo. We went to a great CD shop on Obispo Street where the owner spent a long time with us, opening CDs and playing them for us. Now that the Buena Vista Social Club has revitalized Cuban music, 'Chan Chan' and other songs can be heard over and over again.
We travelled to Cuba via Toronto, which I would definitely advise against (especially if it is during the winter, since you will have to come up with a good story as to why you are tan)! Apparently there has been a lot of collaboration between the US and Canadian governments as of late (the guy driving over the border with explosives over New Year''s and Y2K issues, just to name two examples), and so they have been getting stricter about cooperating with US citizens going to Cuba. The only benefit for going through Canada is that it is easier to work with the tour operators, and they can also book you hotels if you need them. The downside is that they are fairly rigid and they only can book expensive 5-start hotels. Chartered flights are definitely cheaper, but unless you are actually on the package tour for which the flight is chartered for, it''s not worth the hassle and the uncertainty - they can change the flights at any time and you have no recourse.
If you are planning on going to Cuba illegally, it is better to go through Central or South America. Cubans are so used to having US citizens and are so eager for their cash that they will not stamp your passport. In addition, the Center for Constitutional Rights, a non-profit organization in New York, has a staff that is dedicated to assisting US citizens who have trouble traveling to Cuba, which they classify as 'Government Misconduct.' They have a publication outlining travel tips before you go to Cuba, and they also provide post-trip assistance if you are caught at customs on your way back. Unfortunately, they do not have a Web site yet.