Highlights of Cuba: A Four Day Itinerary

Ever since Cuba became a more tangible place for Americans to visit in 2016, I knew I had to visit someday. Despite your political views and opinions on US-Cuban relations, the island is truly a vibrant, historical, and cultural place making it an amazing vacation destination! Even with recent travel restrictions as of June 2019, it is still possible to visit Cuba under the “support for the Cuban people” category (where most travelers fall under, unless traveling for journalism, humanitarian aid, etc.). I chose to book my first trip to Cuba through a tour with Sourced Adventures, a guided tour that covered a majority of travel logistics. This trip was a wonderful and safe way to be guided around Havana and Viñales. And while I could have easily spent at least a week in Cuba, it is most certainly possible to visit and see quite a bit of Cuba in a short amount of time. Here’s my four day itinerary with Sourced Adventures:

Day 1: Arrive in Havana!

A mojito made by yours truly!

Once arriving and getting settled into the city, what better way to start a Cuban adventure than to grab some local food and a mojito! There is something completely satisfying about making and savoring your own mojito! They are a traditional Cuban beverage made with white rum, sugar, lime juice, soda water, and mint. After a long morning of travel, it was quite delightful and refreshing!

Cabernet Show at the Buena Vista Social Club

For our first night in Havana, we were able to experience some Cuban culture through a Cabaret show at the Buena Vista Social Club. With dinner, drinks, and dessert, the Cabaret show is conducted with some of Cuba’s famous performers who even invite the audience to become a part of the show on stage! When visiting the Buena Vista Social Club, do not expect gourmet, fancy dining. But the show of course is the main attraction and well worth the visit for a taste of Cuban culture!

Day 2: Exploring Havana City

Some of many classic car taxis!

Exploring Havana requires at least a full day to squeeze in the main attractions. We wandered through Old Havana, getting a view the Capitol building (which looks very similar to that of the US), as well as the colorful pastel buildings and classic cars. Old Havana also offers plenty of local shops to complete any souvenir needs.

Che Guevara, Revolutionary Square

Of course, visiting Havana would not be complete without seeing the famous mural of Che Guevara at the Revolutionary Square. You will also find Che on t-shirts, postcards, and other souvenirs throughout Cuba.


On the outskirts of Havana city lies Cuban artist José Fuster’s dreamy art neighborhood of Fusterlandia. This artistic park reminded me of Antoni Gaudi’s work in Barcelona with its mosaic style and bright colors.

Ernest Hemingway’s house

To end our long day in Havana, we wandered the property and home of famous author, Ernest Hemingway, also known as the Finca Vigía (“lookout farm”). Hemingway wrote a significant portion of his novels For Whom the Bell Tolls and The Old Man and the Sea here. If you’re lucky, you might even spot a Hemingway doppelganger there (apparently the Hemingway “look-alike” society is a real thing, with its annual contest held in Key West).

Day 3: Viñales Countryside Day Trip

Viñales National Park

After two days in the city, we were most certainly ready for some fresh air. Embarking on the 2.5 hour road trip from Havana to Viñales, views of the National Park made the drive worth it. The best way to explore Viñales is by horseback throughout the valley to experience the serenity of the National Park.

Horseback riding through Viñales

After horseback riding through the valley, we embarked on a tobacco plantation tour, learning about the history and creation of the Cuban cigar. The traditional Cuban cigar includes drying out tobacco leaves and rolling them into a cigar. We even had the opportunity to smoke and buy them afterwards (I opted to taste authentic Cuban rum instead).

Rolling cigars from dried out tobacco leaves

After a long day spent horseback riding and cigar rolling, we were ready for a late lunch before our boat ride tour through a cave and checking out the Viñales Mural de la Prehistoria, a UNESCO World Heritage Site before our drive back to Havana.

Viñales Mural de la Prehistoria


Day 4: Beach Day and Classic Car Adventure

A sunny day in December at Santa Maria Beach!

After a packed 3 days filled with sight seeing, we were ready to relax and enjoy some time lounging at the beach! Cuba has some of the most gorgeous beaches I have ever seen with its white sands beaches and clear turquoise blue water. Even in December, the weather is perfectly mild in Cuba for swimming and sun bathing.

Riding in style!

After a full day of salt and sun, I could not think of a better way to end our long weekend in Cuba than a sunset drive throughout Havana in a classic American car! It was quite nostalgic cruising in a convertible watching the sunset over The Malecón. Even though four days goes by quickly, Cuba makes for a great long weekend getaway!


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