Ah Cuba, the forbidden fruit of the Caribbean. So many questions. So many things unknown. I went into this trip, it felt, with only one eye open. Off limits to American’s for roughly 55 years, travel to the Caribbean nation has now resumed in full force. While it’s still not technically legal for American’s to travel to Cuba for tourism purposes, with the exception of one very expensive piece of paperwork, I had absolutely no difficulties whatsoever in getting into the country, and more importantly, back in to the United States. In fact, it was one of the easiest re-entries to the U.S. I’ve ever had. All while carrying a box of Cuban cigars in my backpack. Go figure, eh?

Since travel to Cuba is still a relatively new (and constantly changing) process, I want to detail for you everything I did to prepare for my trip to hopefully help you should you want to do the same. But take note – policies seem to be changing every day, and even the information written on signs in Cuba are not always accurate. It’s best to still check the State Department site as well as Cuba Travel Services for the latest and greatest.

The most important thing you’ll need for any trip to Cuba is a travel card. It’s not a visa, but I’m not sure exactly what the difference really is. I paid $110 through Cuba Travel Services to purchase it. When it arrived, I was rather taken aback to find a blank form I had to fill out myself. It seems a bit strange that after I entered all the information into the site, I still had to fill it out myself. Seems like a lot of fraud could occur here, but I guess they aren’t too worried about it.

You’ll also need to chose which category you fall under for your reason to visit. Originally I was going to use journalism and this blog, however after talking to my friend who works for a local news station that recently went to Cuba, I realized my small-time blog won’t fit the bill. So I ended up choosing the Educational: People to People category. Basically this means you have to create an itinerary filled with cultural activities – sightseeing, museums, visiting national parks – pretty much anything except lying on the beach for a week. No problem. Those are all the activities I prefer to do when I travel anyway.

Perhaps the most important thing when choosing a category is to decide what your story is and stick to it. But in reality, I was never asked about it at all. Not when boarding my flight to Cuba, not when going through Cuban immigration, and not when re-entering the United States. All that planning, all those itineraries carefully created and printed out were for nothing. I’m still glad I had them though. The US government has up to five years to audit you after your trip to ensure you were there for appropriate reasons, so make sure to keep that itinerary and any receipts to prove you did cultural activities. Easier said than done though, when dealing with a cash-only society. But worth keeping in mind.

After the travel card is sorted, the next task is to book lodging. All hotels in Cuba are owned by the government. They are perfectly lovely places to stay, but I wanted a more authentic experience, and one where I was sure my money’s going to the people. Casa particulares are rooms for rent in people’s homes. It’s expected under communism that if someone needs a place to sleep, they can stay in someone’s home, usually for free. Unfortunately it doesn’t work that way for tourists, but casa particulares are still plentiful and can easily be booked on Airbnb. We only made reservations for our first and second stops in Havana, leaving the rest up to the casa system. Sure enough, our host Lindiana (who I seriously cannot say enough amazing things about) took care of us and made us reservations in homes of people she knew in all the towns we were visiting.

Finally, health insurance is required while you’re in Cuba since US health insurance won’t apply. Most airlines offer this as part of your ticket. It’s worth double checking, and if they do, make sure you keep your stub with you throughout your trip as proof in case you should need it.

Beyond the items listed above, there really was little else I needed to do to make this trip happen. I spent hours and days researching for every scrap of information I could find, but it all ended up being really quite simple. Once in Cuba, my trip went as if it was anywhere in the world. There were the usual travel hiccups of course, but they were easily handled. I hope you find the information here useful if you are planning a trip here yourself, and if you have any questions I didn’t address, leave me a comment and I’ll be happy to share more!

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