3 Perfect Days in Havana Cuba: Here’s How To Spend Them!

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Havana, Cuba

The recent death of Fidel Castro catapulted Cuba to the top of international news, but smaller stories have been making waves here in the United States, especially since the surprise election of Donald Trump on November 8.

Many Americans, present company included, are concerned the President-elect will roll back progress made on U.S.-Cuba relations during the Obama administration, including the ability of Americans to visit Cuba legally.

But many are not: American Airlines’ Cuba routes have been severely underperforming, and it’s unlikely the Dallas-based carrier is alone in it woes.

Although it’s difficult for me to understand why anyone would not want to visit Cuba, what with my incredible experience there last year, I will continue to do my part to promote tourism to the island. Today, I’ll highlight what is the probably the best long-weekend trip in the Americas: Three days in Havana, Cuba’s colorful capital.

Need help planning your trip to Cuba? Hire me as your Travel Coach!

Where to Stay in Havana

Cuba’s accommodation industry is rapidly changing, both in the form of hotel construction as well as with the opening of Airbnb on the island. The most special aspect of my experience in Cuba, however, was using the country’s network of casa particular home stays, and the one I slept at in Havana was definitely the most special of all.

Casa Habana Lourdes not only boasts a location in the heart of Habana Vieja, but Lourdes, a spectacular hostess who not only makes you feel at home, but is priceless is coordinating transport and accommodation all over the island.

Day One: Get Lost in Habana Vieja

When I say Lourdes’ house is in the heart of Old Havana, or Habana Vieja, I mean it: Just a few minutes’ walk west of the front door sits the city’s stunning Capitolio building, while walking eastward takes you into a dense, delightful district of amazing architectures, colorful characters and music that will make you want to dance—even if, like, me, you completely lack rhythm.

Indeed, exploring Habana Vieja is something of a dance, an all-day (and, potentially, all-night affair) that’s less about a specific route and more about evoking a specific feeling. On the other hand, some standout places you’ll want to be on the lookout for including Castillo de la Real Fuerza, the La Floridita bar made (in)famous by Hemingway, the colorful buildings along Paseo de Martí and the immaculate Hotel Inglaterra.

Day Two: Cruise Along the Malecon

Speaking of Hotel Inglaterra, it’s in front of this heritage building that you’ll find what is in my opinion the most extensive and impressive collection of classic cars in Havana. These are cool not only to look at and photograph, but also to hire for the day—or night—and have a drive along the Malecon, Havana’s beautiful waterfront boulevard.

Of course, your Malecon ride is only the beginning of your adventure here, whether you choose to walk along it before or after (the Malecon is home to a variety of public art installations and delectable eateries including the Chilean Cafe Neruda), or allow your drive to take you to one of the live music clubs on its far end.

Day Three: Take a Day Trip to Cigar Country

One of my biggest surprises about visiting Cuba was how easy traveling around the country by bus was—far preferable to driving, which external circumstances prevented me from doing anyway. For example, Cuba’s picturesque cigar country of Viñales is just four hours away by bus, so if you wake up at the crack of dawn (the first bus leaves around 7!) you can manage to visit on a day trip.

Viñales is a paradise, even if you don’t smoke cigars. Although you can easily engage in local activities like horseback riding, hiking and coffee/cigar making with anyone you meet walking through the town center, I recommend you try to find a man named Domingo (pictured above)—contact me personally for advice on his whereabouts!

PRO TIP: If you get back to Havana early enough (to be honest, that will probably be the next morning—I can’t imagine you not wanting to spend a night in Viñales!), Colon Cemetery is huge, picturesque and right near the bus station. It’s also near the historical Revolution Plaza and many other destinations you might not be able to squeeze into three days in Havana otherwise.


Havana is a massive city, so while this itinerary provides a colorful, lively plan for three days there, it isn’t (and isn’t mean to to be) exhaustive. Let’s hope Trump continues reneging on his campaign promises and keeps Cuba open to Americans, so you can visit again and again and discover Havana on multiple trips.

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