HAVANA, CUBA: Expectations

Let’s play a word association game. When I say “Cuba” what do you think of? The first thing that comes to my mind is vintage car. In general, I think of Cuba as a country in a 1950s retro wrapper. When you look up photos of Havana the majority of your results are classic cars in a dizzying array of colors that match the buildings and creates this vibrant fantasy world. I recently read Next Year in Havana by Chanel Cleeton, which prompted my desire to go to Cuba. The book is a dual narrative alternating between the grandmother’s story during the revolution and the grand daughter’s story in present day Cuba. The books goes into the history of Cuba and you experience the main Cuban tourist attractions alongside the granddaughter as she travels around Havana searching for answers about her grandmother’s past. This book coupled with my Dirty Dancing: Havana Nights obsession in high school solidified Cuba becoming my next travel adventure. Below are the expectations I have before the trip. When I come back I’ll do an expectations versus reality post.

Getting There

Let me preface these expectations with, I am from the United States, which has had a very complicated past with Cuba. In 2016, President Obama lifted the tourism ban to allow Americans to travel to Cuba for educational trips, as individuals rather than in tour groups. That being said, there is still a lot of pre-planning you need to do to enter the Cuban country as an American. I’m expecting there to be a lot of questioning at Customs from both the American and Cuban side.

In addition to traveling with your passport, a Visa under the “support the Cuban people” category is required.

You’ll also need to present a trip itinerary at the airport before they will let you board the plane to Cuba. There’s limited direct flights to Cuba. I’ll be traveling from Chicago to Cuba with a layover in Fort Lauderdale, Florida.

U.S. Restrictions, ATMs, Health Insurance, and Phone Service

The United States supplies a list of restricted entities that Americans are not to support. There is a lot on this list and it’s going to be VERY difficult to remember all the restrictions.

In addition to this hefty list, American debit/credit cards will NOT work. Exchanging American dollars at the airport for the correct currency – Pesos Convertibles – is the only possibility for a currency exchange. This will require some guess work for how much money I’ll need to last my whole trip, since ATMs will not be an option.

There are a few articles out there that discuss obtaining health insurance for the vacation. This is something that should be obtained through the Havana airport.

Another important piece of information I learned during my research is American phones will not be able to hook up to wifi and you won’t be able to use data. That means downloading a map of Havana BEFORE leaving since I won’t be able to depend on Google maps. I was able to download a map using the maps.me app. I also printed hard copies to be safe.


I am really really looking forward to the authentic food and copious amounts of daiquiris. In the Next Year in Havana novel ‘ropa vieja’ was mentioned as a signature Cuban dish. I’ll be looking for that on menus.


I’m imagining classic cars EVERYWHERE. There’s just a rainbow-like parade of cars endlessly cruising down the streets.

I’m looking forward to writing about the reality of the trip upon my return!

Happy Travels,


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