Last October, Jared and I went to Cuba. It was an attempt to shake ourselves out of the endless question loop, where we were constantly working out what to do next. I hoped Cuba would bring some clarity, but figured at the very least there would be mojitos.
So did it work?
Well, if there’s one thing I know for sure, it’s that travel does not eviscerate your problems. It may help you temporarily forget them, it may even minimize them, but it does not make them go away. The questions were still there when we got back to Jacksonville, crowding the condo and waiting expectantly for an answer.
But Cuba did what travel does so well, and brought me back to the present moment. It reminded me not to take every decision so seriously, not to be such a maximizer when it comes time to make a choice.
If you like piña coladas
This was especially clear in Viñales, a town two hours west of Havana. Most Cuban tobacco is grown in this area, so it’s a critical part of the economy (no Viñales = no Cuban cigars). Its rolling green hills and rich red soil attract a growing number of visitors, who come to ride horses along the fields and learn the difference between a puro and a factory-made cigar.
When you start each day with breakfast on a terraced rooftop with mountain views, it’s hard to feel stressed out. Instead of researching every possible thing to do and every possible tour operator, we asked our Airbnb host for suggestions.
She was a former doctor who found that there was better money and less pressure in Airbnb, so she left medicine for hospitality. She suggested a horse tour—her brother, a former veterinarian, now leads tours in Viñales for the same reason.
“He treats his horses well,” she said, and that was enough for us.
We spent the next morning on horseback, following well-worn trails past tobacco and coffee farms, stopping to chat, to taste, and to swim. Jared bought a pack of puro cigars to bring to his brother’s December wedding (and we learned, weeks later, how important it is to store them in a humidor; many went moldy in the Florida climate and had to be tossed).
In the afternoon, we pulled up chairs at one of the many restaurants lining the main street. I ordered a piña colada and some soup, having had my fill of mojitos by then, and the waitress came back to check that there was enough alcohol in it. (FYI there definitely was.)
She also brought out a box of dominoes, then laughed from afar as we tried to figure out how to play. Eventually we just took turns matching them up, never really sure what we were doing.
Fake it till you make it
It was the unofficial theme of our Cuba trip—not being sure what we were doing, but giving it our best shot. And you know what? The week was arguably better and certainly no worse than it would have been had we deeply researched each decision.
We were mentally free to just go where we felt like going, without indulging the time-consuming urge to look up reviews or must-do lists. While it did often result in aimless wandering, it also removed the pressure to gather all the information before making a decision.
Our trip started and ended in Havana; both times we stayed at the same Airbnb near a public wifi park. Most days we just walked until we came across something interesting (which didn’t take long) or got hungry (which also didn’t take long).
We walked along the malecón, through the old town, and around the university. We visited museums we had never heard of, greeted the city’s many cats and dogs, and caught the occasional pedicab when the heat got to our heads. We ate ropa vieja and croquettas, drank mojitos and daiquiris, and said “I can’t believe we’re actually in Cuba” at least twice each day.
We didn’t return to Jacksonville with a solution to the then-unanswered question about where we should live—that took another four months. But Cuba helped us step outside of our heads, and offered yet another reminder that you don’t have to have all of the answers in order to move forward.