How to Get to Cuba Illegally (Hypothetically Speaking)
For the past 50 years, Cuba has been our mysterious Cold War enemy to the South, a forbidden place that few Americans were allowed to visit. But thanks to a recent announcement by the Obama Administration that signaled a normalizing of relations with the island, that's about to change. It may take some time, but it should eventually become much easier for Americans to get in.
Sure, right now you can visit Cuba legally, but the purpose of your trip must fit into one of 12 categories -- usually as part of a medical, religious, educational, or cultural program. And while an official license is no longer required to travel with a group, you still can't go for the explicit purpose of smoking stogies and sipping mojitos on the beach.
That said, Americans have been skirting US law to visit Cuba for years, and this is how they do it...
Flying through a third country
Usually people go in through Mexico, but you can also get there from Canada, Central America, or any number of Caribbean nations. You can't get tickets using a typical site like Orbitz or Kayak, though, and travelers usually book directly on non-US airlines like AeroMexico or Cubana Air.
Pre-purchasing a visa
There's a counter at most airports offering service to Cuba, and the process takes about 30 minutes. Prices can vary, but from Cancun it usually runs about $25. Cuban officials will stamp this visa, not the passport (at least not American ones), but visitors who're nervous about the stamp often ask nicely. They also need the visa to exit Cuba, and guard that thing like it's gold.
Pre-booking a hotel
Cuban immigration officers sometimes hassle tourists who don't know exactly where they're going to stay, so a lot of folks book a hotel in advance.
Bringing cash, and lots of it
Foreign debit and credit cards haven't worked in Cuba for years (although that's about to change too), so visitors bring a lot of US dollars and exchange them for Cuban convertible pesos at most nice hotels -- usually at a pretty terrible exchange rate.
Bringing nothing back. As in, nothing but memories.
With the recent easing of the embargo, travelers visiting on an official trip can now bring up to $400 in goods back -- including $100 worth of tobacco and liquor. People sneaking in through a third country not so much. In order to minimize potential trouble, they make sure not to bring anything back that could tie them to Cuba -- no cigars, rum, currency, paperwork, guide books, or even ticket stubs. Nothing to prove they were there.
Playing it cool upon returning to the US
Even with a "Mexican Stamp of Death" (two entry stamps INTO Mexico with no apparent exit stamps), as long as travelers don't do something stupid like list Cuba as a country they visited on an US immigration form, everything is usually copacetic.