Favorite Things to Do in Cuba

Building in Cuba

Favorite Things to Do in Cuba

Parque José Martí in Cienfuegos, Cuba
So much history to see including the Parque José Martí in Cienfuegos, Cuba

Cuba is a romantic island situated in the Caribbean with a rich background and storied past full of intrigue. Add a fascinating cast of characters such as Ernest Hemingway, Hugo Chavez, Ana Betancourt, and Fidel Castro who influenced history all around the world. So, why not embark on an adventure worthy of a novel?

Let’s go to Cuba!

Up in Smoke

Cuban Cigars with Forbes article

The product most commonly associated with Cuba is its cigars. Banned for decades, the increasingly available cruise excursions have brought them to the forefront of the tourism industry. Only 50 cigars per person may be brought back from the island to the mainland legally. High on the list of excursions from the ships include tours of the factories and hand-rolling demonstrations. Lessons on the correct method of smoking and savoring your cigar while sipping Cuban rum makes for the perfect pairing.

Separate varieties of tobacco leaf are used in the making of a good cigar. The outer leaf burns at a different rate than the inner rolled leaves and has a different flavor. In the original factories, you can imagine the many tables with tobacco leaves stacked high with workers rolling the leaves perfectly and tightly into the right shape and thickness, trimming the ends just so. The down side of doing this all day in the sultry, pungent atmosphere of the day is redundancy and boredom. To alleviate the monotony, someone who was literate would read novels to keep the attention spans active – hence the names of the popular cigars, Romeo e Julieta, Monte Cristo, etc.

The Visitor Who Stayed

Ernest Hemingway first visited Cuba in 1928 on a layover traveling to Spain. He was living in Key West, Florida at the time and his next visit was in the summer of 1932. This time he went to Cuba with two friends from Key West: Joe Russell and Joe Lowe. They went to fish the annual marlin run aboard a boat called “Anita”. They also had a Cuban man who they hired onboard to rig baits. A year later, in 1933, Esquire Magazine hired Hemingway to write articles, and he would use his experiences fishing as content for these articles.

Ten miles east of Havana, Ernest Hemingway first rented then purchased a house in the small, working-class town of San Francisco de Paula. His house named Finca Vigia, meaning “lookout house” was built in 1886 by Spanish Architect Miguel Pascual y Baguer. Hemingway purchased the house in 1940 for $12,500. The Cuban people have always respected famous writer’s choice to live in a modest town, amongst the people he fished with and enjoyed spending his time around.

Hemingway, the Author

Earnest Hemingway image with marlin in Cuba
Both Finca Vigía and Hemingway’s Key West home are now museums.

Ernest Hemingway gained fame for his wartime drama novel ‘For Whom the Bell Tolls’ which financed his relocation to Cuba. During one of his typical bar visits, he happened to engage a destitute old patron who was forlorn. As it was relayed to Hemingway, the man was about to be evicted from his shack. He had taken his small fishing boat out beyond the normal range to catch a larger fish to pay for his rent. His true tale became the basis for ‘The Old Man and the Sea’. The novel later became a movie starring Spencer Tracy. The novel ‘A Movable Feast’ was written during his time in Cuba, as well

Call Me Ron

Mojito cockail with Cuban rum
The classic mojito with made with muddled mint, rum, and seltzer water.

Rum (known as Ron in Cuba) is the next most popular product to savor in this part of the world. Made from the locally abundant sugar cane, it is a large part of the economy as the distilleries are a favorite excursion for the tourists. As always, you can choose your level of quality by how much you want to spend. Santiago has its own rum named for it – available at almost any location – and it is less expensive than the least of Havana Club varieties sold at the distillery in Havana.

The bucket list adventure of the tour is tasting Cuban rum and smoking a Cuban cigar and you can look back on the memory of doing them in Cuba. Less than 5% of Americans smoke cigars so everyone in the room is likely a rookie. Included is a mini lowdown on the proper smoking etiquette (let the ashes grow on the end, how to light up, etc.) and production of them. The purchases of rum and cigars can be made at the conclusion of the tour.

Hemingway’s two favorite watering holes in Havana, El Floridita and La Bodeguita del Medio, still stand today. They are very popular with tourists, thanks to the famous writer and the rum drinks he helped to make famous there, including mojitos and the daiquiris.

Ernest Hemingway drinking in Cuba
Old file photo of Ernest Hemingway drinking in Cuba. Click photo for more on his favorite drinks

Classic Cuban Cars

Classic old blue car in Havana Cuba
Classic old blue car in Havana, Cuba

The world has a love affair with the site of bright, colorful, classic old cars. In Cuba, they are numerous even after 60 years in a hot, humid climate. This is not because the mechanics are also magicians, but because the existing engines were replaced with Russian diesel motors. Once the economy was cut off from the United States, Russia was their go-to market for cars and everything else. Turns out their cars’ diesel engines fit our classic cars and diesel is much cheaper than gasoline. At the time, 95% of their economy was with America including coffee, sugar, rum, and more.

Book Your Trip Soon

Horse cart in Cuba
Carts pulled by horses are a main form of transportation around the island.

There are many cruise ships that now go to Cuba, leaving from Miami and several other locations. Flights now go direct to Havana from Miami and Fort Lauderdale too. Get your passport ready and enjoy this beautiful island before it gets too commercialized and starts to look like…well, America.

Like an “off-the-beaten-path” style of travel? Read about Dave’s Greece trip!

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Cuba point of interest


  1. Mary says:

    Great article. Captures the essence of the country.

    1. Rebecca says:

      Yes, so beautiful!

  2. Becky Huddle says:

    This blog is amazing! I feel like I have visited the Countrys and places through your eyes!

    1. Rebecca says:

      Thank you for coming along on the journey!

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