I'm interested in a summer 2009 trip to Cuba. As an educator, I believe that I can get a Treasury Department license to go, but I wondered if you knew of a reputable tour company that knows the eccentricities of Cuban travel and can put together an educational tour for me?
–Sherry, Woodstock, Ga.
First of all, don't be so sure you can get a Treasury Department license until you have one in hand. There are a number of regulations in relation to licenses to go to Cuba, one of which basically states that you must have a valid educational reason to travel to the island. Even if you're an educator, you've got to have a reason to go.
You can see the relevant regulations by clicking here.
That said, hundreds of Americans violate at least the spirit of the rules and mislead the government about their final destination (and thus risk hefty fines). Travelers often fly through a third country (like Mexico or Jamaica), as there are no direct flights between the United States and Cuba, thanks to the embargo. In general, the Cubans know not to stamp your passport.
Remember, because of the embargo, your credit and debit cards and travelers' checks are not going to be accepted. Cuban travel companies, at least most of those that cater to Americans, are often based in Canada, Jamaica, or Mexico, to escape U.S. regulations.