Legal Travel CubaHere’s my final post about my recent trip to Cuba (if you missed the first two, you can find them here and here, plus check out the photo gallery). My editors at ShermansTravel and I have enjoyed reading your comments and input from my initial post regarding the new regulations for U.S. travelers to Cuba, so if you have any additional thoughts – or travel tips of your own – please feel free to share in the comments section below. I’ve already heard about some readers who have trips planned – buen viaje!

Brush up on your Spanish: Beyond just “¿Dónde está el baño?” and “mucho gusto,” that is. Hotel staff, restaurant employees, and some cab drivers usually speak at least a little bit of English, but having some grasp of Spanish will exponentially enrich your experience in Cuba. For one, you’ll help reduce your chances of being taken advantage of as a tourist (like asking how much approximate cab fare is before you get in, and making sure you don’t order a whole fish instead of one portion).


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In addition, you can develop a much more complete picture of what life is really like by chatting with people you interact with on your own, not just through the scheduled activities. For me, having real conversations with Cubans on the street, in cabs and at bars was an unforgettable highlight and critical to an appreciation for the complexities of daily life.


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And your U.S.-Cuban history, too: Never heard of the Cuban 5 or Che Guevara? If not, do yourself a favor and read up on them, as well as whatever else you can about Cuba’s tumultuous history, especially with the United States. It will only enhance your on-the-ground experience, as references to the country’s revolutionary leaders, as well as ongoing issues such as the Cuban 5, are everywhere: billboards, statues, memorials, graffiti, and paintings.

Coming in with a good base of knowledge on the subject (mine was woefully inadequate, which I’m still kicking myself for) will help you make much better sense of  “this chess game that our governments have been playing,” in the words of a Cuban professor who gave us a fascinating presentation about the foreign relations between our countries.

Pack some small gifts: Pre-trip literature from our operator advised against bringing gifts, which I wish I would have ignored. Most Cubans adore baseball, and anything related to American baseball – caps, T-shirts, freebies from game giveaways – makes for ideal presents to give to people you meet along the way. Pens are another easily transportable item that seemed to be in high demand.

Get to the airport early: Lines are long for charter flights to Cuba and full of people traveling with electronics, massive packages, and suitcases packed with goods to bring to family and friends back home. Plus, check in for some flights closes an hour and a half prior to departure. Save yourself the stress and get there at least three hours beforehand in Miami, and at least two and a half hours’ beforehand in Havana.

If you want that stamp, ask for it: For years, the unspoken policy for Cuban customer and immigration officials was to not stamp U.S. passports so that American travelers wouldn’t run into trouble returning to the States. And even though the new legal travel might make the stamp slightly less coveted, it’s still one that gives you some serious travel cred.

But even if you specifically ask, you still might not get it – which, alas, is what happened to me because I mistakenly thought the official was stamping my passport along with my visa. Qué lástima. Guess I’ll have to go back.

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