Cuba Madness

Cuba Madness

I don’t know if I’ll get in trouble for this, but oh well. I dig honesty.

So I thought I’d tell you the truth about my trip to Cuba. It hasn’t happened yet, but the flight is paid for and my accommodation is booked. SNAP. I go very soon, and the trip is long overdue, because I’ve obsessed over it since Destiny’s Child was still a thing. And it was all Armin’s fault. My friend, he took an illegal trip to Cuba about fifteen years ago, and his stories…oh his stories. His photos. His enthusiasm. His damn Cuba trip soaked into my bones and left me with a Cuba crush. I vowed I would get down there at some point, no matter what—fuck the legalities.

So now, many moons later, I’ve decided it’s time—and the way I started planning for this trip has been very different to my others. First, I’ve heard stories about it being legal-ish. Some people said you could go, no problem. NPR said it was still sticky—not totally okay just yet. Others said it was still very illegal, and until that changed, I was rolling the dice with secret entry.

I was, though, told on many occasions that I could go there totally legit if I obtained an “artist” visa. To get that “artist” visa, I’d have to prove an itinerary. To prove that itinerary, I’d have to fill in paperwork that spoke to every minute of every day with valid names, locations, and times of interviews I would conduct in the name of my “artist” research. In other words, I’d have to prove I WAS NOT going down to Cuba to lay on the beach or hang out in a bar full of son cubano, cigar smoke, and rum dreams. And to that I said, “I’m sure.”

I’d have to prove I WAS NOT going down to Cuba to lay on the beach or hang out in a bar full of son cubano, cigar smoke, and rum dreams.

That shit was nevva-eva gonna happen. Yeah right. No way. I was going to get VERY drunk in a VERY Cuban bar with paint peeling off the walls, five guitars being strummed into spontaneous combustion, and me sweating balls while I Pachanga’d my tits off. The rest of the time would be spent face down on the beach.

But how would I obtain my “artist” visa with that story? I wouldn’t. Embassies don’t like tit disappearance tales. And so the next option was to go illegally, but was it safe to go illegally? Was it easy? Could I get away with it? I didn’t know. I didn’t even know if it was safe to research trips to Cuba on my computer. The possibility stood that if I Googled “going to Cuba as an American” a man in black might show up in my bedroom and 2 a.m. to cuff me to the United States and slap a $10,000 fine on my forehead.

So after many hours of pondering and some timid Internet surfing, I made a decision. I would call the Cuban embassy. I would have an earnest conversation about my intentions—my possibly illegal, travel thug intentions of skipping their rules if they needed an itinerary from me. And then—I’d ask them what they thought about them apples.

And that’s exactly what I did.

Stay tuned to read about that weird ass conversation.


Read Shelby’s book, Good Globefor a hilarious look at some of her other adventures.


  • Cate

    I have a dream…aahhh Cuba. Thank you Shelby for showing me the way. I continue to be a fan…