While it’s easier for Americans to visit Cuba now more than ever, it’s still pretty frickin' complicated. Especially if you're not willing to run a marathon through Havana. US laws restrict your itinerary, how much you can spend, how you pay, etc, etc... Yea, seriously, who's up for Puerto Rico?!?
But wait, hold on. Group IST, a New York-based travel company, has recently scored permission from the Treasury Department's Office of Foreign Assets to offer an eight-day tour under the government's "People-to-People" exchange program, and plan to have trips sailing by December.
Yea, that's the best part: You'll be staying on a luxury sailing yacht.