With all due respect, steppie, I doubt that was a strictly legal trip. You got through, yes, but the fact that you put "educator" and "legal" in quotes makes me think you realize it was a wink and a nod. Your art museum sending you there with advance arrangements for you to meet with their Cuban counterparts because, say, they were doing an exhibition about Cuban art would have complied. Simply bringing back some brochures probably doesn't.

If you want to be legal, it must be a structured, organized activity that takes you to Cuba. You can't claim to be a journalist and say you're going to write about your trip to Cuba on your blog or on your Facebook page. It has to be an actual writing assignment for publication. (That's the way I've gone.) You can't claim you are going "in support of the Cuban people" (one of the 12 categories) and stroll the streets talking to people. It must be a trip with an organization that promotes democracy in Cuba.

You also have to devote the equivalent of a fulltime workday each day to the activity that takes you to Cuba. You can't play tourist. There can be no leisure time except outside what’s essentially an eight-hour workday. That's why the people-to-people tours don't take you to the beach. That's why the people-to-people tours require you to participate in all activities. Outside an illness that keeps you confined to bed, you're expected to go on that morning visit to the elementary school, rather than ditch the group and spend the morning shopping.

Yes. Those tours are expensive. Keep in mind that everything is paid for.

Traveling via Canada or Mexico or the Bahamas is the age-old method of sneaking into Cuba as a tourist through the back door. No. It's not legal. Thousands of Americans have done it and continue to do it. It's a decision only you can make.