Cuba Before the Crowds: A Journey Through Time and Hospitality

Originally published May 11, 2017 • Refreshed layout and restored long-form narrative

Havana, Before the Tide

I went to Havana to feel it before the rush—on a budget, moving slowly, and trusting the kindness of strangers. I slept at a family-run casa where dinner tasted of the sea, rode in vintage Chevys that purred like old stories, and found quiet at the Capitolio and Cristóbal Colón Cemetery before ending in the sun at Playa del Este.

The first hello that made me feel at home.

Home, for Ten Days

I chose La Casa de Ana because it looked ordinary—in the best way. Ten nights under $350, a neighborhood that breathed through open windows, and a front door that learned the sound of my footsteps by day three. Ana welcomed me as if we were resuming a conversation, not starting one. Each evening, the table filled with what I didn’t yet know I was craving: lobster one night, shrimp the next, a grilled fish that tasted of smoke and sea salt. Clean linens, small kindnesses, and a sense that someone cared I was there.

Outside, paint peeled from balconies where laughter and radios competed with the rumble of old engines. Life was not curated—it was lived. I treasured that. The house held its own quiet beauty, proof that hospitality is a language that needs no translation.

A room that felt like a welcome back.

Plates that said: sit, eat, exhale.

Getting There, Getting Oriented

My route was practical: Washington, D.C. to the Bahamas, then on to Havana with the help of a local agent. Cuban immigration stamped a visa slip, not my passport, and I tucked it carefully into the pages where I keep things I can’t afford to lose. Cash mattered—U.S. cards were a maybe at best—so I carried enough to keep my days simple. The rule of thumb became this: patience, courtesy, curiosity.

Rolling History

The cars are the first thing you notice and the last thing you forget. A red Chevrolet winks in the sun; a DeSoto floats by like a memory in motion. Many are older than the drivers who now tend them, kept alive by a brotherhood of mechanics whose hands speak fluent ingenuity. Under one hood I saw an atlas of parts—Russia, Germany, China, Venezuela—every bolt a small act of defiance against scarcity.

Not all of them have seatbelts or modern conveniences; most have earned their miles twice over. But when the light hits right and the engine settles into its rhythm, you understand why people keep them—how a machine becomes a member of the family.

Artisans of the everyday, keeping history roadworthy.

Stone, Light, and Names

Havana’s architecture wears its story in public. The Capitol’s familiar silhouette feels like a conversation with Washington, D.C.—not mimicry, but a confident echo. In the cathedrals, stained glass filters the heat into something gentler. I found unexpected quiet in the Cristóbal Colón Cemetery: avenues of marble and angels, where love is written in stone.

On the markers, names I’d grown up hearing in Trinidad—Hernández, Gómez, Martínez, González—bridged islands and generations. History isn’t distant there; it’s the ground you walk on and the faces you recognize.

Wednesday at the Water

Midweek at Playa del Este felt like a secret kept just for me. I arrived before lunch and rented a chair and umbrella, the kind of transaction that makes you grateful for small bills and simple pleasures. A mojito sweating in the shade, a grilled red snapper that tasted like the ocean had told it what to do—then sun, then sea, then a nap that surprised me with its depth.

By afternoon, families and friends gathered in clusters of laughter, the beach stitching strangers into neighbors. Havana is many cities in one, but here it becomes a conversation with the horizon.

Wind, City, Memory

On my last evening, I climbed into a cherry-red ’65 Bel Air and let Havana unspool around me. We drifted past façades that remembered their first paint, past windows that still choose to be open, past people who wave at strangers because it makes the day better. The car’s engine hummed a soft benediction. I thought: this is why I came—to be reminded that places are alive, and that life is not staged.

What Stayed With Me

I left with a pocketful of receipts and a heart full of names. Cuba offered me more than sights; it offered a pace, a temperature, a way of receiving strangers as future friends. The island is not a museum; it’s a conversation—between scarcity and creativity, between history and what comes next, between home and the places that teach you how to recognize it.

Your turn: Have you visited Havana? Share a memory or a lesson you carried home.

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