1. It’s a poor country, and there’s more to it than pretty, vintage cars and Caribbean drinks/beaches. This could be a culture shock for some, especially when we have exoticized it with our social media posts. You should go if you can, but don’t assume it’ll be a purely relaxing trip. The poverty is something to be mindful of and so is the fact that Havana is rich in culture and history and music. If you don’t incorporate that into your itinerary then you’re not making the most of your tip.
2. Machismo is still very much a part of the Cuban culture. If you’re traveling as a solo female or with just another girlfriend like I did, know that it’s safe, but you will get constantly kissed at, catcalled and stared at. Living in New York City, I still wasn’t prepared for the perpetual discomfort of walking around.
3. Ernest Hemingway lived there. For all my literary nerds out there: Hemingway lived in Cuba for 20 years so it’s fun to frequent all his haunts — bars, a hotel lobby and his house.
4. Money. Change it to Euros or CAD before going so you aren’t charged a fee for converting US$. Don’t change all your money at the airport, you’ll get ripped off (you’d have to go to a local bank with your passport to change the rest. There’s usually a line but you get more for your buck). Take more cash than you think you’ll need because you won’t have a way of getting more or using a credit card.
5. Taxis are the main form of transportation. You will get ripped off. It should never cost more than 15 CUCs to get from one end of Vedado to Old Havana. If you’re asking to ride in a nice vintage car (top down, hands up), you’ll definitely be charged more. But as I learned firsthand, walking around from one neighborhood to another is a lot longer than you’d think.
6. Pack everything you need (feminine products, toiletries, etc). You might think I’m being dramatic but I’m not. I’m sure a hotel is different but we did an Airbnb/Casa Particular and even just finding a place with bottled water nearby was very difficult. Also, public places didn’t have hand soap or even toilet seats, so hand sanitizer and tissues are a must.
7. You need to plan in advance. I’m a very laid back, spontaneous traveler, but unless you are in a hotel, or go to one to buy an internet card, you will not have access to anything — weather, directions, business hours, etc. It’s very important that you make sure that you have all of this planned in advance. I can’t stress this enough, because we just trusted the weather would work out when we had a day trip to the beach in Varadero planned. It didn’t. We also trusted hours to bars and museums wouldn’t change from when we looked prior to the trip. They did.
8. Think about why you are going. I had to come to the realization that I went because I could, not because Cuba has been on my list or a culture/history I have been particularly fascinated with for a long time. I don’t even speak Spanish! My mindset was all wrong on the trip and in hindsight I realize that I went for all the wrong reasons. Like I said in #1, I feel like Cuba was exotic, and though I know I’m lucky to have experienced it, I have to honestly admit that I wish I wasn’t so “American” about it and had built up more of an interest, understanding and respect for Cuba before spontaneously going.
9. Don’t worry about customs. I was worried at first, but Cubans encourage tourists. As long as you’re filling your schedule with all the history and culture Cuba has to offer, you’ll be fine. No one at the airport in the U.S. could be bothered and no one I know was ever questioned or stopped on the way back in the country.
10. You can take cigars in your carry-on. We learned the hard way, but up to two cases is fine!
Have fun! I had a very particular type of experience in Cuba, and didn’t enjoy it as much as I could have. But the country has a lot to offer and the trip is definitely a memorable experience.