When you get home and see everyone you know and show them all the photos you’ve taken the questions are pretty standard: Did you bring back any cigars? (no) Did you have any issues with customs? (also no) Then everyone says they want to go down there before it is too late, as though there is some kind of clock on the country. As though at a certain hour of a certain day a maw will open up and remove the very idea of Cuba from our existence. They’re worried that the push of tourism dollars will somehow ruin the country and the prestige of the old will be painted over with the convince of the new.
And maybe it will, but probably not within this lifetime. They’re great people, the Cubans, but they’re also very proud. They’re nice to you to your face, but I feel this is part of some grander ruse to keep you at arms length. To keep all of the things that you are desperately trying to seek in some kind of soul-finding journey at bay. Maybe it is here, maybe it’s not. Either way it likely isn’t for a traveler. This is not for you.
I’ve written a handful of things about the practical nuts and bolts Americans should consider when going to Cuba. The nuts and bolts to traveling anywhere aren’t terribly difficult to figure out. But when you land in a place like Cuba, especially Havana, there is a certain personality required that I don’t see in everyone who insists on hearing the travels. Sure, anyone can plop down a few grand for a chartered tour and see all the things you’re supposed to spend money on and take pictures of. There will always be those tours in any city any where. But going into a place on your own self-facilitated journey is something different.
I’ve always felt like coming back home from a place should leave you feeling uneasy. Maybe you’re more anxious about the world at large or you’re left wondering if the home you’ve picked is the one that you deserve (or even the one that deserves you?). Cuba definitely brings all of this out and it sits with you for a good while. Even weeks later as I punch out the words into this box I’m left wondering about a lot of things I’ve seen, and the things that were kept hidden. Just like how one can never fully adopt a language, a traveller might never actually know the entirety of what they are presented with.
I’m not sure I’m ready to go back to Cuba anytime soon. Not only are there plenty of other places on my list that I’d like to hit up first, but I need to go back with better intentions. I sort of floated through this trip with bad Spanish and guessing about a lot of things. By the end of the second day I was left wishing I had researched more, read more, printed out maps marked up with places that I needed to see or eat or experience. As a result, I sort of just existed, and that’s pretty much why I like hitting the road in the first place – to do something other than exist for a little while.
 Read More About my Travels in Cuba in 2017

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