The Day We Went Off the Resort Map to Explore Santiago de Cuba and the Island of Cayo Granma
We met another couple at the resort who understood a simple truth about 1980s travel: if you want to really see a place, you ask the people who live there. They spoke to the towel attendant — a woman with a warm smile and a calm confidence — and asked if she knew anyone who gave private tours on their day off.
She did.
And she was available.
She even arranged a driver.
That’s how four tourists climbed into a small, spotless taxi early one morning, a black Mercedes with a white roof that looked so polished it practically shimmered, and set off toward Santiago de Cuba, the cultural heart of eastern Cuba.
Instead of the battered car I expected from a country dealing with an embargo, our taxi was immaculately maintained, clearly cared for with pride. When I asked how Cuba kept older vehicles in such incredible shape, our guide explained that decades of scarcity had turned Cubans into master inventors.
If a part didn’t exist, they made one. If something broke, they found a way to rebuild it.
It was the first of many moments that showed me Cuba wasn’t going to fit any assumptions I’d brought with me.
A City Full of Life, Colour, and Contradictions
As soon as we stepped out of the car, the world filled with noise and movement. A group of children gathered instantly, all grins and curiosity. Our companions had brought candy, which made us immediate celebrities. The kids pressed in close, delighted, talking over each other in a joyful blur. It was sweet, very overwhelming, and profoundly human.
Our guide took us first to Castillo del Morro also known as Castillo de San Pedro de la Roca — the dramatic 17th-century fortress perched over the entrance to Santiago Bay. We wandered stone corridors worn smooth by centuries, and the ocean crashed below, sending salt mist into the air.
It felt like walking through a living history book.
Quick Facts: Castillo del Morro | Castillo de San Pedro de la Roca
- Location: Overlooking the entrance to Santiago Bay
- Built: 1638–1700
- Purpose: Defend the bay against pirates and foreign attacks
- Architect: Juan Bautista Antonelli, Italian military engineer
- UNESCO Status: World Heritage Site since 1997
- Fun Detail: Its zig-zag fortifications were designed to absorb cannon fire.
Lunch on the Forgotten Island of Cayo Granma
After exploring the fort, we boarded a small boat across the harbor to Cayo Granma; a tiny island once filled with beautiful wooden stilt homes built by American and Cuban families.
By the late 80s, many had fallen into disrepair, but one old home had been restored into a restaurant.
We invited our guide and driver to join us for lunch, something they might never have been able to do otherwise. The food was simple and fresh, but the conversation made it unforgettable. We asked about their families and their lives. They chose their words carefully, with the quiet caution that hinted at the political climate more clearly than anything they said outright.
Quick Facts: Cayo Granma
- Location: In Santiago Bay
- History: Once home to early-20th-century wooden waterfront houses
- Name Origin: From Granma, the yacht that brought Fidel Castro ashore in 1956
- Tourism: The restaurant we visited was inside a restored stilt home
- Storm Damage: Heavily hit by repeated hurricanes, especially Sandy (2012)
- Vibe: A place suspended in time — more memory than destination
The Shoe Store Moment I Still Think About
Later that afternoon, we walked through Santiago’s streets and went into a tourist mall where we passed a small shoe store. Our guide paused, noticing a pair she knew her daughter would love.
The shop was closed, but even if it hadn’t been, she couldn’t have gone inside. It was a tourist-only store and off-limits to Cubans. When I offered to return and buy the shoes for her, she quickly and quietly shook her head.
She wasn’t angry. She was afraid.
It was the first moment I truly felt the gap between my life and hers.
The Currency No One Talked About
We’d brought Canadian dollars, assuming that was the right approach. Instead, people discreetly asked for U.S. dollars.
In 1989, American currency was technically illegal, but it was also the most valuable thing anyone could carry.
It was one more contradiction in a day full of them.
We ended the day watching cigars being hand-rolled before heading back to the resort, but first we dropped our guide at home.
We pulled into her neighborhood; a cluster of concrete apartment blocks wrapped around a long communal courtyard. I pictured kids kicking a ball there, or families gathering in the evenings. But that day, the entire courtyard was filled with a single, silent line of people.
A bread line, our guide explained, her voice quiet but matter-of-fact.
The contrast hit hard. We had just finished a seafood lunch on Cayo Granma, chatting freely and eating as tourists, and here were the everyday realities of Cuban life laid out in front of us. It was a moment that settled deep in my chest and stayed there.
After that, the rest of the ride back to the resort felt different — quieter, heavier in some ways, but clearer too. What we’d seen that day stayed with me, shaping how I understood the country long before I had the vocabulary for it. By the time the resort came back into view, I felt like I’d crossed an invisible line between “traveler” and “witness.”
New Year’s Eve: When Everything Came Together
By New Year’s Eve, I had finally stopped comparing the trip to what I thought it should have been.
I let Cuba just be Cuba.
Only then did the magic arrive.
We paid extra for the late night holiday dinner. Early that morning, the staff jumped into the ocean and dove for fresh lobster, an act of generosity I didn’t fully appreciate until years later. That night, they grilled the lobsters outdoors over open flames. The shells blackened, the meat glistened, and the smell — smoky, salty, buttery — is something I can still conjure instantly.
The cultural show that followed was full of dancers, musicians, drummers, and stories. At 24, I didn’t recognize the blend of Spanish, African, and Indigenous influences. I only knew it was beautiful.
Then came the mojitos.
Then the music.
Then the dancing.
We danced barefoot under the stars, sweaty and laughing, surrounded by joy that felt raw and uncomplicated. When midnight hit, the entire resort erupted in hugs and shouts, a tidal wave of celebration.
And somewhere between the dancing and the laughter, I realized:
This wasn’t the best night despite everything we’d gone through.
It was the best night because of everything we’d gone through.
The rocky beach.
The shortages.
The lines.
The moped adventure.
The dinosaurs.
The dolphins.
The giant rock climb.
The fear in the shoe store.
The bread line at our guide’s home.
The quiet stories over lunch on Cayo Granma.
All of it built toward that night — a night that shifted how I travel and maybe who I was becoming.
The Lesson Cuba Saved for Last
I didn’t have the words for it at 24.
I do now:
When you stop forcing a place to be what you expected, you finally get to experience what it actually is.
And sometimes, what it is… is unforgettable.
Coming Up Next: The Many Lessons Cuba Taught Me
After this final installment, I’ll share one last post. The lessons that stayed with me long after I flew home. Cuba changed how I travel, how I see people, and how I understand myself. Those insights were the real gift of this journey.
Read the Cuba 1989 Travel Series
A five-part memoir of a trip that changed everything.
Part 1 — Arriving in Cuba: The Other Side of the Island
Part 2 — The Resort That Wasn’t What We Expected
Part 3 — The Moped Adventure Through Baconao
Part 4 — The Giant Rock & the Moment Cuba Opened My Eyes
Part 5 — New Year’s Eve in Santiago & Cayo Granma
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