I chose to go to Cuba to celebrate my 24th birthday and close out the hardest part of the law school application journey: the LSAT. My friend Ashley, who I had only known for a short 4-5 months at the time, was crazy enough to take this trip of a lifetime with me. We’ve been tight ever since!
Cuba was truly magical. It’s my favorite country to date and I can’t wait to return. The Cubans blew me away with their kindness, hospitality, resiliency, and pure joy they exuded despite their circumstances. Cuba is completely cut off from Western civilization, but that’s what makes it so charming. The vintage cars, old crumbling building, lack of internet access, slow pace of life — it’s all so refreshing. It really feels like you’re stepping back in time. We spent a beautiful 7 days in Cuba, my only regret was not staying longer.
The best way to experience Cuba is to cut yourself off from civilization and immerse yourself with the locals.
LODGING
I highly encourage anyone going to Cuba, regardless of your level of boujie-ness, to stay at a casa particular (AirBnB). This is so important, especially if you chose “support of Cuban people” as your travel exception. You are putting money directly in the pockets of the locals. Additionally, there is no better way to get to know the locals and to gain first-hand knowledge of Cuban life and recommendations for places to eat/things to do than staying at a casa particular. And they are sooooo cheap, hello savings! We stayed here. Our host and his sister were so sweet and helpful during our stay, they even took care of my friend when she got ill, gave us the best recommendations, set up taxis for us when we left to Trinidad, and for $5 a day cooked us breakfast on the roof.
We stayed right outside of Old Havana. It was a 10-minute walk into the heart of Old Havana and about 15-minute walk to the Revolution Museum. I was very happy with our location, but if you want to be in the thick of things, definitely book your casa particular in the center of Old Havana.
GETTING AROUND
A lot of people hire drivers while in Havana. You get a personal driver in a vintage car that will take you anywhere your heart desires with great recommendations. Being budget conscious, we opted out of the personal driver. It helped that both my friend and I spoke Spanish so communicating wasn’t an issue and we had no problem flagging down a taxi or a bike taxi to get around. Many Cubans in Havana speak English very well, so you shouldn’t be concerned about communicating regardless.
When hailing taxis negotiate everything! Most taxi rides should only cost between $5-$15. Anything above that is a rip off except for going to the airport which should be $25-$35. We got our taxi to Trinidad (4 hours from Havana) for $40 per person which was steal! Our casa particular host arranged it for us. Although the price was great (tour operators and vintage car taxis were charging $100+), we were in a dingy little car. I personally didn’t mind, since I like blending in with the locals when I travel— it’s all part of the authentic Cuban experience.

We split our trip to Cuba by locations- 4 days in Havana and 3 in Trinidad, a small colonial town. While in Havana, we did just about everything there was to do except for going out dancing at La Fabrica de Arte, a popular art gallery and club in Old Havana, which was closed, and catching the sunset at the Castillo De Los Tres Reyes Del Morro. I recommend adding both places to your itinerary.
EXPLORING HAVANA
On day one in Havana we explored all of Old Havana. We first stopped at La Floridita, a 200-year-old restaurant, to have the famous Cuban daquiris. It was packed, but we were eventually seated. We sat in the center of the restaurant enjoying our daquiris and listening to a live Salsa band. Note: well-known restaurants and bars will charge more than normal for food and drinks. A drink in Cuba should range from $2-$6 and food $5-$10.

We continued to walk around Old Havana for the day. There is a lot to see and explore! From all the hole in the walls restaurants and bars in between side streets to small shops. Take it all in. We were stopped by a gentleman who was offering a guided walking tour; we turned him down many times but he insisted on bringing us to a local bar known for their mojitos. He then brought us to a salsa club to get tickets for the night performance; which we also fell for. Luckily, we ended up enjoying our night. But we later found out that anywhere these tour guides bring you they make a commission from.
There are a lot of these tour guides everywhere in Havana. You’ll be annoyed by them because they approach so often and are relentless, but please be kind to them and respect their hustle. Cubans are very poor and the wealth distribution is painful to see, therefore, many Cubans make a living off tourists. The $1-$3 dollars they get off you will put food on their table.
LEARNING CUBAN HISTORY
We spent day two in Havana immersing ourselves in Cuban history. We first went to the Revolution Museum and spent nearly 4 hours there. You pay a small entrance fee of $7 USD. This was my favorite part of our time in Havana. I learned so much about Cuban revolutionary politics, the art of political propaganda, and the story of Castro’s seizure of power. Most importantly, I learned about Cuban’s love and respect for Fidel Castro and the false propaganda America told us about his political party as well as the heinous acts of violence America committed against Cubans.
We then hailed a vintage taxi that brought us to the Callejon de Hamel — a block in Havana dedicated strictly to the religious practice of Santería. Santería is a practice brought to Cuba by the African slaves and is still practiced in Cuba today. It was beautiful to see Cubans proudly embrace their African roots. Our tour guide was a sweet young man with lots of knowledge on the practice.
In the evening, we had dinner reservations (you must make them, our host took care of that for us) at the famous La Guardia restaurant where Beyonce and Obama once ate. The food was amazing! The best food I had while in Cuba. This was the most expensive meal we had while in Cuba, by Cuban standards at least. A 4-course meal ran up a bill of $80 between my friend and I.

Later that night we bar hopped and then ended up at a night club on the outskirts of Havana. It was at least a 20-minute car ride and definitely in the rich neighborhood of the Havana suburbs. I’m talking mansions kind of rich. That was where I realized just how significant the wealth disparities were in Cuba. I could barely believe my eyes, it was as if I was back in America! Apparently all the rich political figures of Cuba lived in that area.
For our last day in Cuba we had planned to go out partying in town with some friends we made, but unfortunately those plans came to an ubrupt end due to my friend getting gravely ill after an allergic reaction to pizza. It was an extremely scary situation, especially being abroad, but our host was extremely helpful and gave us medicine that would eventually calm her allergic reaction after hours in bed. Another reason why you should stay at a casa particular! We suspect the salami/ham used as a topping was the cause for the reaction.
Once we stabilized her and she was resting, I decided to wander around Old Havana solo talking to the locals. They are all so friendly and eager to share their life experiences with you. I sat at a local sandwich shop and ate El Cubano— authentic Cuban sandwich while talking to a few locals. I walked away so inspired and heartbroken from hearing their stories of triumphs, joy, and resiliency while surviving in Cuba.
We then took off to Trinidad for the rest of our stay. Read about that leg of our trip here. To read 6 things you must know before going to Cuba, see this post.
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