It's an interesting topic. I have a UK passport, so would have no problem going to Cuba ... if I could just convince the BF to take a holiday for once in his life! But that's another story.
Anyway, I found this site:
http://mediastudy.com/articles/bdcuba2.html... which includes the following info:
The regulations, cold-war era dinosaurs enacted over 40 years ago, effectively curtail tourism by prohibiting American citizens from spending money in Cuba. Still, about 60,000 Americans a year, including hundreds of wealthy Floridian yachters who pack Havana’s Hemingway Marina, exercising what they call their “right to freely travel,” ignore the edict. Put bluntly, Cuba is chic. It all started about three years ago when The Washington Post published a travel piece puffing Cuba, turning blowing off the embargo into a jet set sport. More recently, the June 2001 issue of Cigar Aficionado devoted a full 85 pages to, as their cover promises, stories about how to “travel” and “invest” in Cuba, sponsored by the likes of Dewers, Hennessy, Lincoln and Netjets, a personal aircraft broker. If you expected Cuba’s hotels to be populated by bohemians and communists, you will be sorely disappointed. The presence of so many wealthy conservative tourists in Cuba, however, has so far kept the State Department, for political reasons, from aggressively enforcing its tourist spending ban.
If civil disobedience isn’t your game, however, another 80,000 or so Americans travel to Cuba legally each year under State Department sanction. Currently full time journalists and researchers, Cuban-Americans visiting relatives under “self-defined” circumstances of humanitarian aid, students enrolled in licensed Cuban Studies programs such as the one at UB (645-3912) or Americans traveling on “fully hosted” trips paid for by foreign nationals such a Canadians, can all travel to Cuba without applying for a specific State Department license. Other Americans who wish to perform or lecture in Cuba, attend a religious or cultural event, engage in athletic competition, work on a humanitarian project or study or independently conduct research for a book can apply for a specific State Department license to travel in Cuba. For more information see
http://www.treas.gov/ofac or
http://www.cubatrade.org/visit.htm.
The State Department also licenses a number of travel agencies to provide legal tourist travel to Cuba. It works like this: built into your package tour is a tuition or membership fee which makes you a “student” or “member” of a licensed “educational” or “humanitarian” group. These trips, which usually depart from New York City or Miami, usually cost three or four times the price of a Canadian tourist package departing Toronto, but include a full itinary of guided tours. Global Exchange (800-497-1994), Cross Cultural Solutions (800-380-4777) and Marazul Tours (
www.marazultours.com) all have good reputations and a long history of arranging legal travel to Cuba.