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My Solo Trip to Cuba

Traveling to Cuba is something I never thought I would be able to do. It wasn’t a well talked about destination growing up. I learned the story of USA and Cuba relations in my high school history classes. And later in life I would hear a family story about one of my mom’s sibling’s history class assignment on Cuba. One of them wrote a letter to Fidel Castro requesting information and the FBI showed up at their house. I also remember having many Cuban classmates at Northwestern who shared their experiences about not being able to travel back home. I say all this to say, I did not think I would ever be able to experience this beautiful country.

In college I started to hear talk about how the Obama Administration would begin to ease travel restrictions among other things with Cuba. I knew many people who booked planned their trips to Cuba and talked about the great time they had there. I knew I had to jump at the opportunity because restrictions could also return at any moment.


I booked my tickets in August of 2017 to travel in December of 2017. At the time Delta Airlines had direct flights to Havana, Cuba. I paid about $400 roundtrip. Americans are not supposed to spend any money that supports the Cuban government, so hotels were out of the question. I booked an AirBnB soon after booking my flight. I chose to stay in El Vedado, a neighborhood in Havana, because it was recommended to me by my linesister who traveled there a few months before me! I also used AirBnB to schedule three activities the week prior to leaving. I was also given a list of recommended restaurants/activities by another friend who traveled to Cuba earlier that year. Americans must also take whatever spending money they want in cash because our debit/credit cards do not work in Cuba. This was probably the hardest part of planning for me. My trip was about 5 days long. Cuba is a pretty inexpensive place to travel so I budgeted about $100. I took out $1000 just in case. I actually purchased the moey through an online money exchange agency. They told me my money would be there the next day, but it never arrived! I was so worried so I ended up going to the currency exchange in Lenox Mall and getting $200 exchanged and I kept the other $800 in USD and I decided that I would just exchange it as needed in Cuba so I did not have to pay a double exchange fee just in case I did not use all $1000. With my passport, flight, AirBnB booked, and my money, I was ready for the trip!

One the day of I parked my car at PreFlight Parking in Atlanta and I headed to the International Terminal. I got to the gate kind of early to make sure things would go smoothly. I got my Visa and filled it out VERY carefully! If you make a mistake, they will charge you $50 for a new one. (The first Visa is included in your plane ticket.) Then I got breakfast and called my mom for a pep talk. This trip originally wasn’t supposed to be a solo adventure, but that’s how it turned out. My mom has a way of telling me to suck it up and pull it together. Her exact word were “Kieara! Pull it together! You cannot be out here crying while you are traveling alone! People will take advantage of that!” It’s exactly what I needed to hear at that moment. So I dried my eyes, ate my bagel and waited until it was time to board.

God knew just what I needed on that plane ride because my seat mate was very friendly and funny. We shared past travel experiences and we talked about what we planned to do in Cuba. People have differing comfort levels when deciding to travel to Cuba and how tightly they would stick to the guidelines set in place by the government. Technically you aren’t supposed to have much down time “vacationing” in the country. My seat mate went through a travel agency that set up a schedule for him and his friends while they were there. This schedule could potentially serve as proof to Customs when he returned in case they asked any questions about why they were there. I did not take this route. Once I got off the plane, the journey began! I had five adventurous days that I will never forget!


Places to eat:

- La Guardia (The Oscar-nominated, Cuban film Fresa y Chocolate filmed here.)

- El Flordita (This the bar the Ernest Hemingway frequented when visiting Havana. Their daiquiris, music, and service are all A1!)

- San Cristobal Paladar (A restaurant that all the celebrities visit when traveling to Havana! The owner and my waiter were super sweet!)

- Really any street place. I just walked and stopped when I was ready to eat.

Places to Visit:

-Viñales (It was about a 2 hour drive by car. My experience host set up the car service. The drive was BEAUTIFUL!!! Once we arrived, you could tell that it was still a huge tourist destination, but it was also a much slower pace than Havana.)

-Malecon (It’s basically the boardwalk. I enjoyed people watching here.)

Other activities:

- Fabrica de Arte (Such a great vibe! The art was great! The music was great! The people were great!)

- 1830 for great salsa dancing! (Even on a weeknight this place was packed! Wear comfortable shoes and be prepared to dance the night away!)


- Explore Silence Valley Walking or Riding by Daily (AirBnB)

  • We hiked the countryside and I learned how cigars are made then I rolled one myself! The people who invited me to their farm did not have any electricity. They lived a very simple life and they were very happy! I enjoyed our conversations!

- Cooking a Tasty Meal in a Cuban Home by Raquel and Chely (AirBnB)

  • These ladies were wonderful! They taught me so much about Cuban food in such a short amount of time. I did this experience with a brother and sister also visiting from the US. The food was delicious. We ate Ropa Viaje, rice, black beans, salad, plantain, and guava shells! We made mojitos!

- Explore the City’s Architecture by Yaneli (AriBnB)

  • This tour taught me a lot about Cuban history and current events. I also learned about the education system. My tour guide just had a child and she was trying to save up money for her son’s education expenses for when he turned 5. Her husband was of Spanish decent so her son would be able to get into a better school. This opened my eyes to the inequalities that exist in education in Cuba, just like in the US.


  1. Don’t be afraid to get lost (well during the day time)! I know this sounds like a terrible tip, but as long as you know the address of where you are staying, you will be fine! This happened to me on my first day in Havana. I left my Airbnb after freshening up and I planned to walk to Old Havana before going to my scheduled tour. Well long story short, I thought I would take a 40-minute walk there. Somewhere I took a wrong turn, but I ended up seeing so much more of the city. I actually got a better sense for the city and in the following days I was able to navigate better. I also ended up at the tour by accident right on time! It worked out perfectly!

  2. Download the Google Maps map for your area before leaving the states. I did not have access to WIFI at all times so this was helpful. My seat mate actually told me this tip as we were backing away from the gate!

  3. Give someone back home your flight and accommodation information. One day I decided to sleep in and I did not get to call my parents in the time frame that I normally would. They spent the money to call my AirBnB host. My host then called me on the cell phone they let me borrow.

  4. Try the local foods! You never know when you will be able to get the local cuisine authentically again! (Personal opinion, the Cuban food was not exactly my favorite. I pretty much ate grilled chicken, black beans and rice for every meal. That’s what was one the menu at every restaurant. It wasn’t terrible, but it also wasn’t extraordinary.)

  5. Ask questions! This is where I learned so much about the country. My tour guides were so willing to share their stories with me!

  6. Wifi is scarce! Get your access card early from a phone company or someone selling it one the street. You don't want to be out of luck at night when you need it! To find a place where there is wifi, just look for all the people gathered and looking at their phones! Remember those spots so you can come back throughout the week instead of always having to look for a new place.

Cuba was such an amazing experience that I didn’t even know I needed! It is definitely a place that I would recommend for anyone, be it a solo trip, friends/family trip, or baecation! Cubans know how to have fun. Also, this is probably the country I felt the safest visiting. If you can get there, GO!

If you have been to Cuba, what was your favorite thing about your trip? Share below in the comments!

Love y’all!


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