Travel Wisdom, Lessons, and Reflections from a New Year’s Eve in Santiago de Cuba, 1989
Some trips entertain you.
Some trips relax you.
And some trips — usually the ones that don’t go as planned — leave you with the kind of travel wisdom you carry for the rest of your life.
My week in Cuba in 1989 was one of those trips.
It began with confusion and disappointment: a rocky beach, a resort short on towels, a diving fatality just days before I arrived. But somewhere between moped adventures, stone dinosaurs, bread lines, and a New Year’s Eve lobster feast grilled over an open flame, Cuba gave me something far better than perfect weather or turquoise water.
It taught me how to travel differently — with presence, humility, curiosity, and a willingness to be changed.
These are the five lessons gained through Cuban travel wisdom that still shape the way I explore the world today.
1. Don’t judge another culture through the lens of your own life
At 24, I arrived in Cuba expecting a version of the Dominican Republic — soft beaches, bottomless towels, and a predictable all-inclusive cocoon. Instead, I found volcanic rock, rationed supplies, currency contradictions, and daily life shaped by political limits I didn’t understand.
None of it made sense to me then.
Only years later did I understand the realities behind it — the U.S. embargo, restricted trade, and the creative resourcefulness Cubans needed in 1989.
This trip taught me a lesson I still remind myself of:
You can’t use your own life as the measuring stick for someone else’s reality.
You have to meet places — and people — where they are, not where you expect them to be.
And when you do, the world opens up in ways guidebooks can’t prepare you for.
2. Fear doesn’t always mean danger — sometimes it’s an invitation
I collected a whole list of “fear-laced but unforgettable” moments on this trip:
- Climbing a massive rock with no guardrails
- Swimming alone with dolphins in a pitch-black tube
- Running from a stranger in an empty amusement park
- Navigating a bustling city full of unknowns
- Riding mopeds through rural Cuba with no map, guide, or plan
None of those moments were inherently unsafe.
But each one pushed me beyond the familiar.
I learned something I still believe today:
Fear is not always a stop sign. Sometimes it’s a sign you’re alive and paying attention.
If you stay present and keep going, fear often dissolves into awe.
Most of the highlights of my Cuban adventure began with that flicker of fear.
3. Don’t outsource your safety — trust your own instincts
Cuba taught me that “safe” and “dangerous” are rarely universal ideas. They’re personal calculations.
Being told something is safe doesn’t make it so.
Being told something is risky doesn’t mean you shouldn’t do it.
Traveling in Cuba forced me to make my own assessments:
Would I climb a ladder into the sky with no rails today? Probably not.
But I looked, evaluated, and chose for myself.
Would I jump into deep water where I couldn’t see what was beneath? No.
But at 24, I took the risk — and it became a once-in-a-lifetime experience.
The travel wisdom here?
Collect information. Listen to your gut. Make your own call.
It’s how I’ve traveled ever since.
4. Not every moment needs a photograph to be remembered
Some of the clearest memories from my trip to Cuba aren’t in any album:
- The man carrying piglets in a backpack
- The breadline filling a long courtyard in our guide’s neighborhood
- The smoky scent of lobster grilling outdoors on New Year’s Eve
Some of those moments couldn’t be photographed.
Others just… weren’t.
Years later, driving toward Truckee at sunrise as wildfire smoke painted the sky in surreal colours, I thought of that man with the piglets. I couldn’t pull my RV over for a photo. So I did what I’d done back in Cuba:
I let the moment sear itself into my memory.
And it did.
That’s when I understood a truth I couldn’t articulate at 24:
If a moment matters, you won’t forget it.
Presence creates stronger memories than any camera ever could.
5. Your mindset shapes your trip more than the destination
Cuba didn’t change.
I did.
When I stopped comparing the resort to what I thought it should be…
Stopped wishing for better beaches…
Stopped trying to force the trip into some glossy brochure version…
Everything shifted.
Suddenly the dinosaurs were magical.
The dolphins felt like a blessing.
The scarcity made the lobster dinner extraordinary.
The cultural show felt like an invitation into the island’s heartbeat.
I realized:
You can’t control a destination — only the lens you experience it through.
When you let go of expectations, the magic finally has room to arrive.
Final Reflection: The Travel Wisdom Cuba Gave Me
I boarded the flight home from Santiago de Cuba with something I didn’t have when I arrived: a different relationship with uncertainty, with culture, and with my own capacity for wonder.
Cuba taught me how to travel — not by itinerary or checklist, but by presence, curiosity, and humility.
It taught me to slow down.
To stay open.
To pay attention.
To listen more than I speak.
To hold moments instead of collecting them.
To let every journey be what it wants to be, not what I expect it to be.
And above all, it taught me this:
The best experiences in life rarely follow the script.
They happen when you stop trying to control everything…
and start letting the world surprise you.
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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