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(Last Updated On: February 3, 2021)

Remember when I went to Cuba and was going to blog about it? Hah! Well, here it is 8 months later!! Traveling to Cuba as an American has a lot of fear and uncertainty around it. I’ll tell you what to expect and how to follow the rules to have an easy, unforgettable trip.

old havana

Before you Travel to Cuba: Preparation

  1. Obviously make sure that your passport is valid and isn’t expiring while you are there.
  2. Call the airline/airport that you will be flying into before Cuba to ensure they have the US to Cuba Visas available at the gate. We flew into Miami from Seattle and filled out and paid for our Visa at a kiosk at our gate. Our visa was around $160. There is an option to purchase online and have it mailed to you.
    1. Keep all of the papers they give you, as there is an exit visa that you will need to exit the country back into the US.church
  3. Download the App maps.me and download the map for Cuba. You can save places prior to traveling. This will come in handy as WIFI is essentially non-existent.
  4. Figure out your budget. Unlike most places you travel to, Cuba does not have ATMs (not even at the airport) that work with US bank cards. Enter Cuba with ALL of the cash you will need for the entire trip and convert it at the airport. We booked as much as we could for Airbnb and lodging before hand so that we didn’t need to shell out money for that as well.
    1. This is why some people will advise not to rent a car, if you incur damages and don’t have the money to pay it…uh oh. Taxis are relatively cheap, and I’ll touch on that. cuba streets
  5. For the Visa into Cuba you need to select a category from the 12 that are allowed for US travel into Cuba. We stated that we were traveling under the category “SUPPORT OF THE CUBAN PEOPLE”. Tourism from the US is “technically” illegal.
    • Support of the Cuban People includes: meeting with local businessmen, artists, tobacco manufacturers. This category also includes visiting independent museums, markets, taking dance classes or cooking classes. Going to art shows and talking to locals also falls under this category. Basically – you can’t come and lay on the beach for 5 days.
      • The US recommends keeping your receipts for up to 5 years to prove a full-time schedule supporting this category. (6 hours a day). Let me tell you, I did not receive a single receipt from any local business. You are paying with cash. There are no receipts. We documented where we went and have not had a problem.
      • Avoid Government buildings and operations. This includes taxis. As US citizens we are required to avoid government taxis and hotels/resorts. Another reason why Airbnb is perfect for this trip. There are plenty of private taxis that will aggressively ask you if you need a ride pretty much constantly. Look for the P on their license plate.
      • FYI: If anything goes awry, there is limited US Embassy services available due to recent attacks on the US Embassy employees in Cuba. sunset
  6.  Health. Check with your primary care physician to check which vaccinations they recommend before traveling to Cuba.
    1. Also, you may want to pack toilet paper. It was a 50% chance the bathrooms had toilet paper. You can pay a bathroom attendant sometimes for toilet paper if you do not have your own.
    2. I should also note that you can only drink bottled water. We were cautious about eating only cooked vegetables, as raw vegetables washed in the water and/or handled by people with unwashed hands can make you very ill. It wouldn’t hurt to pack some Pepto-Bismol. None of us became ill during our time in Cuba.


Regarding WIFI

Getting WIFI was truly a run-around. We had to go to a specific establishment, usually a hotel, and had to purchase a 2-hour WIFI card. Initially, they stated they didn’t have any cards left, but after we talked to 4 different people, we walked away with a card. Our Airbnb host also offered us WIFI cards as long as we pay up.

Okay, cool, so you got the WIFI card. Step 2. Go to one of the FEW locations that has a WIFI hookup. Hotels and some parks had it. You could tell you were in the right spot if everyone was standing around on their phones. You can use Maps.me app to search ‘WIFI’ and see where the nearest hotspot is.

Then you enter the login information on the card, and the time starts ticking! You can log off at any time to conserve whatever you want of the given 2-hours. So, like I said, a run-around for sure. Honestly not even worth the hassle unless you need to contact family.

ALRIGHT. Now the fun stuff!! Explore Cuba!!



We spent 4 nights in Havana collectively.

Arriving in Havana:

Our Airbnb host sent a taxi for us. Another perk of using Airbnb in Cuba. All of our hosts were VERY helpful in telling us where to go and what to do.

We stayed in the neighborhood El Vedado, known for pre-revolution luxury mansions. This location gave us quick access to the Malecon, a seawall that stretches along the coast of Havana.

In this neighborhood is the Fabrica de Arte Cubano (FAC). The FAC is a cultural venue in a renovated cooking oil factory. There are three levels and a multitude of rooms. Some rooms display contemporary art exhibits, other larger rooms feature dance performances and cinema. At night, there are bars on every level, music and dancing. We had a wildly fun night here with some Australians we had met the day before.

For our food recommendations, we asked our host or locals we met. Knowing some Spanish will really help you out. Basic knowledge of reading menus and for communicating for transportation. My friend Brenna was our translator as she had spent a few months in Peru and learned Spanish.

street photo

photo of me by Brenna Buckwalter

Day 2

We wandered the streets of Old Havana visiting some of the famous churches and eating gelato.


Day 3

We went to Playa Santa Maria and hung out on the beach, paying locals for mojitos and cornrows. I think I still dream about those mojitos.

Our last night in Havana before heading to Viñales, we rented a catamaran to stay on for the night. We went to the marina market and ended up cooking up quite the pasta meal. We enjoyed sun, a tropical storm, and one of the wildest sunsets I’ve ever seen. The catamaran had 4 bedrooms and 4 bathrooms. It was a LARGE boat. We had to remain docked, but there is an option of paying to take the boat out.


Oh, how I miss this place. When I think back to Cuba, I think of the horses we rode into the tobacco farm with mountains surrounding us. The people were as warm as the golden hour that engulfed us as we road back to the family that was hosting us.

vinales valley

We took a 3-hour taxi that was arranged for us by one of our Airbnb hosts. I remember it being around $30-40 per person. The driver arranged to come back at a set time the next day to pick us up and take us back to Havana. Because of how reasonable taxis were with a group of 4 people splitting it, we couldn’t justify renting a car

We spent one night here, and it did not feel like enough time. We wandered the streets at night and talked to locals and gazed at the stars while enjoying our Cuban cigars.


We did two tours of tobacco/coffee farms. The tours were pretty similar. We ended up doing two because we had booked one before arriving to Cuba. Upon arrival to Viñales, the family we stayed with convinced us to go to their family farm as well. Airbnb Experiences allowed us to book one in advance. We learned it cost a bit more than paying when in the city.

tobacco farm

The tour allowed us to learn how to roll a Cuban Cigar, as well as purchase cigars from the farmers. Because Cuba is a communist country, they by law must give 90% of their crop to the government. The remaining 10% they can use for cigars for family and friends, but they will not have the iconic government label. We bought only from the farmers, as they boasted of no chemical treatments and old recipes that have been passed down for decades.

You are allowed to bring $100 worth of goods from Cuba into the US. I claimed $50 worth of Cuban cigars and had no issues coming through US Customs.

rolling cigar

Back to Havana (Ooh, na, na)

We stayed at another Airbnb that was closer to Old Havana this time. It had a view of the ocean and was right across the street from the Malecon. We used this day to get any last-minute souvenirs before flying back to the States.


More Photos:




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