Hemingway’s Tour: A Havana Evening Back in Time

It’s twilight on the rooftop of one of the most famous hotels in Cuba. Travelers from around the globe are seated at tables, talking, enjoying a drink or a plate of food. The atmosphere is cozy, yet refined. Waiters dressed in tuxedos with bow ties, and lights were strung around the large pergola covering the bar as street sounds drift lightly towards the sky. The stucco walls are painted a cheerful coral and the only reminder that you are still in this decade is the single TV that hangs behind the bar.

We sit and enjoy a cocktail. When we started, the sky was a bright pink with hints of purple. As the night goes on it turns to an inky black. Looking out over the wall you can see the skyline of Havana. The steeple of La Catedral, the rooftops of other buildings and when you peer down further, the people down below, laughing, eating, relaxing and enjoying themselves. Further out you can see where the land meets the water. Distant lights nestled in the hills across the Port, the lights from distance objects further out that sway slightly with the water.

The service is slow and the cocktails were not very good, but I would not want to be anywhere else at the moment in time. Compared to the Hotel Nacional, the Hotel Ambos Mundos was the second best in Cuba, yet Ernest Hemingway refused to stay anywhere else while in Cuba, and sitting on that rooftop at twilight, I can understand why. The experience is enchanting from the moment the sliding metal gate closes on the vintage elevator and its operator whisks you to the 5th floor. Even in Cuba, it is like being given a portal back in time.

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Pretty in Pink

My recommendation is to go to the rooftop of the Ambos Mundos for an aperitif. Get there around 5:30-6:00 PM so you can watch the sunset, and stay for an hour or two while you enjoy the atmosphere and some drinks. Afterward, head to either O’Reilly 303 or 304 (O’Reilly #304 | Habana & Aguiar -they are across the street from one another) or Ivan Chef Justo (Aguacate 9, Esquina Chacon) for dinner. Both are in walking distance from the hotel and have excellent food, especially Ivan Chef Justo. You may have to wait for a table, but that’s ok, just ask to be seated at the bar and enjoy more cocktails, because you will never find them as cheap or as good as they are in Cuba. My personal favorite are the caipirinhas.

When you are finished with dinner, you can walk a little further down the street and enjoy another Hemingway favorite, a daiquiri at The Floridita. It’s perhaps one of the most famous spots in Havana, but any Hemingway fan must get a picture with the bronze statue of the man himself, cast in his favorite bar stool. Again, the atmosphere can whisk you back in time, as you are served your favorite drink by a bartender in a red jacket and bow tie. The place gets packed quick though, so its best to stay for one drink and then head out.

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An Ode to Hemingway

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A Havana Classic

If you still have a little life in you after a long day in the sun, there is one more stop on this little Hemingway tour, La Bodeguita la Habana. Take a stroll back towards The Ambos Mundos, and you can find this gem at C. Empedrado entre Cuba y San Ignacio. It’s a tiny little place, and you will find both its patrons and its lively atmosphere spilling out into the street. You may have to squeeze your way inside to order a round of mojitos, but you can enjoy the place all the same whether you are standing inside or on the street. You may even see people who came just to watch the party from afar! As usual, expect great live music and an even better time!


Hemingway really got it right when he chose Cuba as a place to call home. This is just one evening tour of some of the most well-known of his favorite spots, but you can’t help but feel fulfilled by the end. I liked to end my nights in Havana with a little stroll around Havana Vieja, just soaking in the beauty and life around me, and reflecting on all I was able to experience that day.


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