This is the most beautiful land that human eyes have ever seen

…said Christopher Columbus upon discovering Cuba in 1492. I had a similar rush of emotion upon first sight of the island and it would continue to grip me throughout the trip. As many may be aware, throughout his presidency, President Obama helped restore relations with Cuba. He was the first U.S. president to visit Cuba since 1928, marking the end of over 50 years of hostility between the two countries, which began during Castro Revolution. Cuba, a country enriched with culture and history and just 90 miles from Key West, Florida, is in the midst of many travel destinations within the Caribbean. Despite the close proximity to the other islands, landing in Cuba is a much different sight.

Havana, Cuba

The Capital in Havana

Landing in Cuba

As our plane was landing, I glanced out the window to take in the aerial view when I noticed most of the streets were dirt roads through the rural towns. A precursor to understanding the lack of government funded infrastructure throughout the country. Upon landing, the pilot notified the cabin that the airport was “closed” and to sit back as this may take some time to resolve. This was certainly a first for us and my imaginative mind started racing, asking “Will we have to fly back to the states? Is there a military coup? Did one of us illegally enter Cuba somehow and not know it?”. Everything turned out just fine.

Classic cars in Cuba

Classic Cars in Havana


With the minor setback, we looked forward to immersing ourselves in the country’s culture and further understanding the impact of communist rule on the people who had lived under it for many decades. Our first impression was from the kind, welcoming, and hospitable people of the island. Hence, around every corner, people would reach out with gracious hospitality and ask questions, offer advice, and generally shower you with warm kindness. Although we only stayed for five days, we made a true effort to learn and get to know the people and their stories.

We spent two days in Havana exploring the streets and historic sites of the city. Note the highlights and key places to explore and activities to undertake:

Havana Activities:

  • University of Havana in Vedado – walk down Avenedia de los Presidentes at night and appreciate the youthful energy of the students enjoying each other’s company on this avenue
  • Smoke a Cuban cigar at Hotel Conde de Villanueva (Mercaderes, corner of Lamparilla) or at Hotel Nacional overlooking the Malecón
  • Ride an antique/classic car – they’re everywhere and cheap, you’ll have no problem
  • Fabrica del Arte: A art at night scene and dance club – get there before 9:30 pm on the weekend to avoid the long, painful line
  • Enjoy a sunset on the Malecón


Riding in a classic car i.e. our taxi for the day

El Malecon in Cuba

El Malecon

Eat and drink in Havana:

  • La Guardia – do not miss this life changing cuisine experience in Centro Habana. Since it gets busy, make a reservation a week in advance confirm reservation 24 hours before
  • La Bodeguita del Medio – the best mojito in Havana with a lively crowd and take in the moment
  • La Floridita – Hemingway’s favorite cocktail bar for a daiquiris – enjoy the live music scene
  • 304 O’Reilly’s – A delicious private place to eat in Old Habana, go early and make a reservation for later. Must eat the empandas and octopus appetizers. Order a watermelon mojito
Drinks in Cuba

Mojitos at dinner

Getting around the island – hire a driver!

Back to painting the picture of the Cuban experience. On day 3, we hired a driver to drive us to Playa del Este in a classic car. Playas del Este is a 30 minute car ride from Havana offering white sand beaches and delightful getaway from the streets of Havana. Our taxi driver, Rafa, ended up becoming our companion throughout the trip and ultimately our entire stay, driving us back and forth from Old Havana to Valle de Viñales on their second to last day. We got to know him well after spending several hours with him in the car, we were able to converse with him using the basic Spanish we learned growing up! My friend, Sasha, spent a few months working at Chipotle when he was younger and claimed he picked up a lot of his linguistic skills while on the job there, such a worldly guy!

Playas en Cuba

Playas del este

Valle de Viñales

Valle de Viñales (Viñales Valley), is a national park and home to many tobacco plantations, where one can find many traditional farms and villages. Once there, we visited the coffee, tobacco, and sugar fincas, squeezed in some horseback riding and visited Cueva del Indio (Cave of the Indian) where you can take a boat ride through the caves. Before the Spanish colonized the area, the Taino Indians held tribal meetings in this area and made numerous carvings in the walls of these natural limestone caves.

Vinales, Cuba

Valle de Viñales



Overall, we had an unforgettable experience in just a few short days and with restored relations between the US and Cuba, now is the time to head over and appreciate Cuba’s beauty, history and the warm kindness of its citizens!

For more adventurous posts, check out the blog page!

For further information and tips on travel restrictions and entering/departing Cuba, I recommend the Expert Vagabond’s post on this topic.


Museum of the Revolution

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