Cuba: Culture, Cars, and a Journey Through Time

Cuba, my 86th country, is a mesmerizing travel destination offering a captivating blend of vibrant culture, stunning landscapes, and rich history. While cars, bars, cigars, and salsa are often the first things that come to mind, what stood out most for me were the people, the sense of safety, and the cleanliness.

My recent journey from St. Thomas, U.S. Virgin Islands to Cuba—via Miami—was made seamless by the expertise of Maria Romeau, Senior Travel Consultant at CubaPlus Travel. Normally, I love to “wing it” and immerse myself in local culture, booking accommodations and transport on the go. But Maria explained how challenging that can be in Cuba—and she was right. She arranged most of our reservations and itineraries, which made for an unforgettable trip.

We began in Old Havana, staying at the beautiful Hotel Loma del Angel. A red 1957 Chevy Bel Air convertible whisked me away to the hotel, where I met my friend Pat Davis, who flew in from Charleston, SC. That night, our driver—who also happens to be a doctor earning $150 a month—took us to Fangio Habana, a rooftop jazz club at the Claxon Boutique Hotel in Vedado. It was an incredible evening, showcasing some of Cuba’s top jazz artists.

The next day, we explored the cobblestone streets of Old Havana, visiting Plaza Vieja, Plaza de la Catedral, and Plaza de Armas. After walking for hours, we hired a horse and buggy with a guide for a ride through the historic streets and along the Malecon, Havana’s famed seaside boulevard.

A few hours west of Havana, we traveled in a lime green and cream 1956 Mercury to Viñales with our driver Alexander. The Viñales Valley offered breathtaking scenery and a glimpse into rural Cuban life, including a stop at Cueva del Indio—a fascinating cave with an underground river. Maria booked us into Finca Villaverde, a charming guesthouse surrounded by nature.

Before arriving, we enjoyed a farm-to-table lunch at El Cuajaní, a countryside restaurant nestled at the base of a mogote—a distinctive limestone hill. This place was a standout: rustic, delicious, and deeply memorable.

Just outside Viñales, we visited the Hector Luis Tobacco Farm and learned about the traditional methods of growing and drying tobacco. Watching a cigar being hand-rolled—and trying it later—was one of the most authentic experiences of the trip.

On the way to Trinidad, Alexander’s car broke down briefly. Within 15 minutes, we were back on the road—now in a burgundy 1941 Buick Super with a new driver, Emilio, who stopped at his house to grab clothes before continuing with us. We paused for a traditional Cuban lunch at a riverside glamping spot before heading to Trinidad.

Our late arrival at Casa Amistad was met with delight. Behind massive wooden doors was a serene tropical courtyard. The property, dating to 1830, has been thoughtfully restored and offers a comfortable, historical ambiance. It’s centrally located and just minutes from the Municipal Historical Museum and Plaza Mayor. We danced to live music in the streets and soaked in the vibrant local culture.

On the return to Havana, we stopped at several sites including the Bay of Pigs, a butterfly farm, a botanical garden, and the city of Cienfuegos—known as the “Pearl of the South.” Each stop added something special to the journey.

Cuba is incredibly accessible, with five direct flights a day from Miami. I flew in with my U.S. passport and purchased a visa for $85. I brought a large suitcase filled with useful items—medications, bandages, children’s coloring books, and crayons—and cleared customs without issue. It was a joy to share these items in the small towns we passed through.

If you’re interested in traveling to Cuba, I’d be happy to help.
Reach me at: CaptJan2@gmail.com or 704-277-6521.

Jan Robinson is a travel consultant, health coach, 2019 CYBA Hall of Fame inductee, chef competition coordinator/judge, and author of the Ship to Shore Cookbook Collection—available on Amazon and by email at CaptJan2@gmail.com.

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