Shana’s Travel Diaries: Cuba


Cuba…has stolen my heart. My weeklong adventure in my greatly anticipated trip to the island has come and gone and I’m left with a passport stamp, tan lines and souvenirs as proof of my time spent there. The trip has been a dream of mine for so long, I have to remind myself daily I was actually there and that I didn’t just imagine it.


I find that for many people, the appeal of Cuba stems from the mystery that it is; and I wanted to uncover a piece of that mystery. Along with five other students from my study abroad program and our travel guide, Jose (@onmyway_rd), I embarked on this trip with pure excitement for what was in store for us. We all had different motivations and expectations for going to Cuba, but together we understood the significance of what we were doing and just how unforgettable this experience would be.


After eight days and sixty-six miles of walking and wandering the streets and alleys of Havana, I was in love with the city and my heart ached (almost as much as my feet) because I didn’t want to leave beautiful Havana. Looking back on my week in Cuba, not only was I able to learn more about this extraordinary country, it’s beautiful culture and people, but I also discovered the beauty in spontaneity and that sometimes the best days of our lives are the ones that take us by surprise. And although there were days and nights we walked to the point that I thought I wouldn’t be able to walk anymore, I would do it all over again in a heartbeat.


Our trip began the morning of Thursday, April 28 at a time when most of us were just getting in from a night of celebrations. A little after six am, we left for Santo Domingo and my restlessness grew as Santiago’s lights diminished from my view. Not even the gloomy weather that had been plaguing the city for the past two weeks or the fact that I was running on two hours of sleep could dull my mood. The only thought in my head kept me in high spirits: I’m going to Cuba.

¡Estamos aquí en Aquí!

Thursday 4/28- 3 miles

From Santiago to Santo Domingo, Santo Domingo to Panama City and finally Panama City to Havana, after more than twelve hours of traveling we finally made it to Cuba. In the taxi ride from the airport, I took some time to reflect, something I would be doing a lot of during the trip due to not having access to Wi-Fi. It was dark outside and well past eight pm by the time we got going, but I made sure to get a window seat. I watched as we drove by people on street corners, cars, buildings and endless propaganda signs. From my time in Jamaica and the Dominican Republic, as well as my short visit to Haiti, I found that I was able to easily pick up on differences between these neighboring islands. I couldn’t help but notice how clean and light Cuban air felt and how smooth the roads were. We arrived at our hostel, which was located right behind el Estadio Latinamericano, the stadium in Havana used for baseball games and was where the friendly game between Cuba and the US was played during President Obama’s historic trip to the island in March. We quickly chose our beds and after meeting Lester and Denise, two Cubans who worked for the hostel, we left to head to dinner. My first meal in Cuba was at “Aquí,” a privately owned restaurant not too far up from the stadium that became our go to dinner spot for the remainder of the week. After a rich and satisfying meal of rice and chicken, we headed back to the hostel and fell quickly asleep.

“Oye, you don’t want to take our picture?”


Friday 4/29- 10 miles

On our first morning, we woke bright and early with the rising Cuban sun and set out for Old Havana by foot, stopping along the way for a cup of freshly squeezed sugar cane juice at a nearby shack. We spent the majority of that first day walking to get an overall feel for the city and stopping only to take pictures here and there. Because of filming for Fast & Furious 8, one of the streets we wanted to walk down was closed so we decided to end our day and head home. By the time we returned to the hostel later that evening, we were all exhausted and craving a cold shower. Although I saw a lot that made me excited for the rest of the trip, I came home that day feeling quite unsatisfied. After a semester of having weekly excursions with planned activities and itineraries designed to help us immerse ourselves in each experience, I had become so accustomed to having a schedule to follow, telling me what I should do. Because of this, I felt as though I had wasted my first day in Cuba and began to worry that my trip wouldn’t live up to my expectations. Despite this feeling I had, I introduced myself to our French hostel mate, Julien, and had a pleasant and intriguing conversation with him about Cuba, Latin America, our personal travels and reasons for coming to Cuba. I was genuinely surprised that when I told him that I was Jamaican, he automatically referenced Usain Bolt and Shelly-Ann Fraser-Pryce. Needless to say, my conversation with Julien cheered me up and left me excited for the rest of my trip.IMG_5632


Saturday 4/30 – 7 miles

The next day, after visiting a local Cuban corner store for breakfast where I got one of the best ham and cheese sandwiches I’ve ever had, we set out for a day at the beach. On our forty-five minute walk to Old Havana, we stopped at Plaza de Martí to enjoy a performance of people playing music and singing while the crowd that gathered around danced to Cuban Reggae. We finally left for Cayo Santa Maria, and along with a new Swiss friend named Ramon, we enjoyed a relaxing and fun day at one of the most beautiful beaches I’ve ever been to. The clear blue sky with water to match seemed like something out of a dream for sure. Upon returning, we quickly went to dinner and got ready for our night out at La Fábrica de Arte Cubano, a project intended to introduce people to the art and music of Cuba in a way contrary to the one many of us are accustomed to. My time at La Fábrica was easily one of the best nights of my life. The atmosphere, the art, the people, the music and live performances, the drinks…the overall vibe was incomparable to anything I’ve ever experienced and I recommend it as a must-do for anyone visiting Cuba. Check out this website to read more about the mission of the project and be sure to watch the video!

Eating un cubano en Cuba!


Sunday 5/1 – 11 miles

After a little under five hours of sleep, a few of us woke up early (or so we thought) to attend the remnants of the Workers Day Parade. Instead of going back to our hostel to sleep away the day, we decided to walk to the city and spent the morning enjoying each other’s company and lovely Havana. With no specific destination in mind, we roamed and wandered the streets and ate Cubano sandwiches in the park together for lunch. Later that night, I experienced another amazing and memorable moment that I’ll never forget. We visited La Plaza Revolución in the Vedado area of Havana where the famous cuadros of Che Guevara and Camilo Cienfuegos are located. Seeing the cuadro of Che Guevara was something I had longed to do and so finally getting the opportunity felt like a dream come true. I remember I couldn’t stop smiling that night and I knew that was what true happiness felt like. We ended up spending the rest of the night walking and experiencing La Habana Vieja at night. We visited El Floridita, the famous bar known for its daiquiris and for being one of Ernest Hemingway’s favorite spots in Havana. On the streets, we saw people out and about, drinking, dancing, singing, laughing and enjoying life and I was once again reminded of how happy I was to be where I was.


Monday 5/2 – 15 miles

Following our long and exhausting night, we returned home around 2 am and woke a few hours later to the hostel being fumigated. While making our trek to La Habana Vieja, we encountered the Fast & Furious 8 movie being filmed, so we joined the crowd of people gathered around the gates to watch a car scene take place. Anyone who knows me understands my obsession with the Fast & Furious franchise and how much of a big deal this was for me. We then went to the Cathedral of Havana San Cristobal, one of the oldest in all of the Americas, where for $1CUC, you could climb one of the towers to see the amazing view of the plaza. Next, we encountered a mercado of Cuban artisans selling handmade crafts, jewelry and other items of art where I was able to get a lot of my souvenir shopping done. It was an interesting and extraordinary environment to be in and I enjoyed the experience. Later that day, I met and interacted with many interesting locals on the street, including a few Reggae and Bob Marley lovers, Luis and “Lolo Rastaman,” who were pleased to find out that I was from Jamaica.


Tuesday 5/3 – 10 miles

On our second to last day in Cuba, we went to New Havana. Before the day’s activities began, we stopped at a corner shop named La Grotte for breakfast. The eatery was laid back and welcoming with bright yellow and red walls that we were allowed to sign before leaving. With full stomachs we walked first to the University of Havana and spent some time on the campus relaxing (there were a lot of stairs so this immediate break was greatly needed). In New Havana, we visited the Coppelia ice cream parlor, which is famous for being not only one of the largest ice cream parlors in the world, but for its feature in one of the most widely viewed Cuban films: Fresa y Chocolate (a movie I’d highly recommend watching). Next, we headed to the Malecón where we took pictures of and inside some of the classic cars signature to the country. Interestingly enough, we were informed by one of the car owners that many of the cars had been used for the Fast 8 movie, and that this day, the same cars were to be used for the Coco Chanel fashion show that was being held in Havana. To end the day, we spontaneously visited the historic Hotel Nacional de Cuba and were lucky enough to receive a free tour and information session about the 1962 Cuban Missile Crisis at the museum located in the hotel’s gardens.



Wednesday & Thursday 5/4 & 5/5 – 10 miles

We devoted our final day in Cuba to do typical tourist things. We visited the Museum of the Revolution, The National Museum of Fine Arts of Havana and shopped for more souvenirs. We ended the day with a tour of the city in a 1951 red Cadillac, making stops at interesting sites such as La Plaza Revolución and John Lennon Park. For our last Cuban meal, we unsurprisingly headed to Aquí where we enjoyed another great dinner, talking, laughing and sharing our favorite moments of the trip. It began to rain heavily and I couldn’t help but think how fitting the weather was for how I felt to be leaving Cuba the next morning. After retreating to our hostel one last time, we spent the night packing and some of us went to the Malecón to hang out. The next morning, we said our goodbyes to Havana and set out for a long day of traveling as we made our way back to Santiago.

Rincón de Los Cretinos aka Corner of the Cretins: “Fulgencio Batista–Thank you for helping us create the Revolution, Ronald Reagan– Thank you for helping us strengthen the Revolution, George Bush Sr. — Thank you for helping us consolidate the Revolution & George W. Bush–Thank you for helping us make socialism irrevocable.”


In retrospect, the trip didn’t go as I had imagined it would and for that, I am grateful. It was better than anything I had hoped for and by the end of the week; I felt an inexplicable attachment to the country already. Because of Jose’s approach to traveling, we were able to experience Cuba in a way that made the trip unforgettable. Each day seemingly started out the same and there were moments when we were all frustrated because we wanted to be “doing” something. However, although we would begin the day walking down the same streets, we always encountered something new and different that we hadn’t noticed before and I think that was what made this trip so amazing. We weren’t on a schedule or in a rush to get somewhere; we simply wandered and got lost in Havana, which made for the best experience and reminded me to enjoy spontaneity in life and to cherish each moment no matter how insignificant it may seem.

Be sure to check out my Photo Diary to see all of my pictures from Cuba!

From Cuba…with love,

SK xo



  1. Wow Shana, this is great stuff! I can see that journalism is not only a passion of yours, but a gift as well! Fashion, history, what’s next! 😊 Like I said last Sunday, “the sky isn’t the limit, it’s just the beginning” (not my quote). 😊 May God continue to bless you!

    Liked by 1 person

  2. Hi Shana, i must tell you i enjoyed reading your travel diaries, your description of Cuba leaves nothing to the imagination, it’s like i was there along with you guys, continue to do what you do best, I’m happy I had the pleasure of meeting you, your on the path of being the greatest journalist yet. You go girl.


    1. Wow thank you so much for your kind words! And thanks for reading 🙂 it really means a lot to me!


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