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Why you should underplan your vacation (or how we ran out of money in Cuba)

Posted in the following categories: Life Lessons

Earlier this year, my wife and I took our first trip to Cuba.

Cuba is a paradoxical mix between the past and the present, communism and newfound freedoms, and architectural beauty and decay. But if you’re like others I know, you have little interest in hearing the rest of my explanation of Cuba’s magnificence and why you should visit the country before its urban centers turn into Cancun.

No, you’d much rather hear the story about how we ran out of money.

You see, despite restored Americans relations, there are still numerous logistical difficulties to visiting Cuba. U.S. currency isn’t accepted, nor are U.S. bank cards or credit cards. Websites like Paypal also don’t work. This means cold, hard cash is required to pay for everything you need–from your hotel to your meals.

To mitigate that uneasy feeling of lugging around uncomfortable amounts of cash, I unearthed a Turkish credit card that had been collecting dust in one of my drawers (I’m a native of Turkey). The card hadn’t expired. I tend to be apocalyptic in my thinking, so I even tried the card at a local coffee shop in the United States to make sure it worked before we left.

Imagine my surprise when the check-in clerk at our Havana hotel informed me that the card had been declined.

“Can you try again?” I pleaded. The clerk grunted and ran the card a second time, as I waited with held breath.

“Declined,” she replied.

We stared at the walls of the hotel lobby, painted in an unsettling shade of brown, as we brainstormed options on the standard-issue hotel notepad: (1) fly to Miami, only 90 miles away, for a “quick” ATM run; (2) ask one of the flight crews staying at our hotel to bring cash for us; and (3) significantly cut down on the amount we had budgeted for the rest of our trip.

We opted for option three. As the prostitute said to the sailor, “It ain’t how much money you’ve got, honey, it’s how you use it.”

This meant that, despite slashing our budget, on the very last day of our trip, we had barely enough money to get to the airport from our hotel.

After we were dropped off at the International Terminal, I felt like Rocky at the top of the Philadelphia Art Museum. We had zero dollars to our name, but we had made it!

My optimism quickly turned into unease as I stared at the departure monitors in our terminal, scanning for our flight.

It was nowhere to be found.

I quickly found an information desk and inquired about the status of the flight.

“Alaska Airlines, Terminal 2,” the desk clerk said.

“Which way is Terminal 2?” I asked, assuming that it was a quick walk or shuttle ride away.

“It’s 3 kilometers away,” he replied.

“Can we walk?,” I asked.

“It’s a highway. You might get run over by car.”

I stared at the clerk in disbelief. After I pressed for alternatives, the clerk informed me that we could take a local bus to Terminal 2, but that would still require a fare of one dollar per person.

Those were two dollars that we didn’t have.

This left us with no other options but to resort to panhandling. My wife Kathy, who is far more attractive and charming than I am, took to asking complete strangers waiting in line at the money exchange if they can spare a dollar.

After some pleading and offering two Cuban cigars from one of our plantation tours, she found two people willing to make a small deposit into their karma bank.

With two dollars in hand, we boarded the bus overstuffed with locals and made it to Terminal 2 (where we coincidentally ran into Jodie Foster).

There are two morals to this story.

First, don’t ever assume that your Turkish credit card will work in Cuba.

Second, and far more important, the greatest travel stories involve trouble, not triumph. I’m a perpetual over-planner, but overplanning can take the joy out of travel. When I look back on my travels, the memories that stand out don’t involve art galleries, museums, or fancy French restaurants. They involve running out of money in Cuba, getting lost in Barcelona, bar hopping in Budapest ruin pubs, and food poisoning in Chile.

But that’s a story for another day.

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