lauras rambles - havana cuba - plaza vieja

HAVANA, CUBA: Reality vs. Expectations

Remember that word game I played in my first post about Cuba? Those initial feelings held true! The colors on the 1950s cars and buildings just made for a fun vibrant travel destination. In this post I’ll be looking at my trip expectations and writing about the reality of my adventure.

Getting There

EXPECTATIONS: 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.

REALITY: Questions from Customs? Not really. No questions from the Cuban customs and the United States asked very minimal questions based on the customs form filled out on the plane. In light of the new Trump administration ban on Americans traveling to Cuba in tour groups, I would caution you to be prepared for more questions from Customs if you are traveling under the “support the Cuban people” visa category.


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

REALITY: Yep! This was true, each airport looked at and/or stamped my passport and reviewed my travel visa. The visa was most important for entering and leaving Cuba. Upon entry this was stamped and at departure it was kept by the Cuban official after he stamped it. I’d recommend taking a picture of this pre-stamped and once more after the Cuban official stamped it upon entry. Don’t be like my dad and realize the night before you leave for home that you have misplaced your visa and now need to unpack EVERYTHING to try to find it. Keep this in a safe place during your trip and REMEMBER where you left it.


EXPECTATIONS: 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.

REALITY: By “itinerary” the U.S. just wants to know you have a return ticket home. I took “itinerary” as a breakdown of each day’s activities so I showed the employee at the Fort Lauderdale airport my 5 day breakdown of vacation activities and she looked at me like “are you kidding me.” So, be sure to have a print out of your flight confirmations to prove you are coming back to the U.S. I recommend still having a breakdown of your activities along with your flight confirmation. FYI, she wasn’t going to let us on the plane to Cuba if we didn’t show her this. Once we did, she stamped something that we had to then carry to the gate and show the attendant there along with our passport.

This was after our mad dash through the airport because our plane leaving Chicago was delayed 2 hours. It was a bit stressful because we thought we’d have to find seats on the next flight to Cuba so at the arrival gate we asked someone about switching tickets. This woman was in a bad mood and told us we better run to the gate because the flight was being held for us. So we ran through the unfamiliar airport trying to get to the gate, while my dad’s leg starts cramping up, just to find out that we had to go to a desk FIRST and show the itinerary BEFORE we can even get through the gate. Just know this is a two step, two desk process, so leave yourself enough time.


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

EXPECTATIONS: 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.

REALITY: I printed this list out for reference and brought it on the trip. I swear Habageneux is everywhere and as an American you can’t patronize those establishments. That includes Hemingway’s room located within a Habageneux hotel. Again, because of the new travel restrictions there will likely be more scrutiny placed on American tourists in Cuba, I would be extra conscious of where you go in Cuba and KEEP YOUR RECEIPTS. The U.S. Treasury can summon your Cuban travel receipts up to five years after your vacation.


EXPECTATIONS: 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.

REALITY: I didn’t even try to use my debit card while there. I exchanged about $400 USD at the currency exchange outside the main Havana airport doors. This lasted my whole six day trip. I was however, more frugal than normal when eating out and purchasing souvenirs since I knew I was limited by how much money was in my wallet.
When you are deciding how much money to exchange, keep in mind how many days your stay is and if you have a frugal personality or an “I’m on vacation so I’ll treat myself” persona. This way you can judge if you need more or less money exchanged. If you do find yourself running low on pesos convertibles, worst case you try to find a souvenir shop owner that will exchange more money for you.


EXPECTATIONS: 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.

REALITY: We asked around the airport where to get this health insurance and no one had any idea what we were talking about. We even had someone translate for us and still no health insurance. So we didn’t get this and were fine. If you do figure this out though let me know!


EXPECTATIONS: 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 app. I also printed hard copies to be safe.

REALITY: and Google Translate saved me while in Cuba. Not literally, but my phone had no signal. Downloading the Havana map and Spanish/English dictionary before I left helped out a lot. allowed me to mark sites I wanted to see before I left for vacation. I urge you to also mark on the map where you will be staying. Even though you are offline in Cuba you’ll still see an arrow indicating where you are on the map. I also printed a hard copy of the map for reference in case I lost my phone or something. Didn’t really use this, but we marked down our walking routes each day so it turned into a souvenir. It was actually nice being unplugged from the internet and social media for a week.



EXPECTATIONS: 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.

REALITY: What I had and saw the most of was ropa vieja. It was delicious! There was also ham on A LOT of menu items, like pizza! I pretty much lived off ham/onion pizza and ham/cheese croissants. I recommend going to Paladares, but do your research beforehand so you know where they are located. They weren’t easily identifiable.



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

REALITY: YES! Classic cars were everywhere! There were classic car tours that took you around Havana. Be sure to do this, they are a blast! There are also classic car libre taxis available. The really fun way to get around though was a Coco Taxi. It was basically a large yellow shell attached to a motorbike.


The colorful, diverse, walk-able city of Havana, Cuba was an amazing experience. I encourage everyone to visit and support the Cuban people!

Have you been to Cuba? Let me know your thoughts below or if you have any questions!

Happy Travels,




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