What to Expect When Flying Into Cuba from the United States
What to Expect When Flying Into Cuba from the United States

What to Expect When Flying Into Cuba from the United States

I stepped off the plane directly onto the tarmac where government agents waited nearby in a large, stuffy, sad-colored rectangular room. A small television played a wrestling match in the center of the holding area, while all the passengers formed five extremely well-behaved lines. Some of us looked nervous. I definitely was. Oblivious to our anxiety, a beautiful little girl with black hair and pink barrettes ran circles around the room’s columns until her mother stumbled over to pick her up. Her mom wore thick stack heels which made her look wobbly. A third of the female passengers wore the same style shoe in various colors. Thick, plastic, blocky stilts. The men wore gold colored watches and creative hairstyles: mohawks, half-shaved heads, and spikes. It was a sign of the timewarp we’d soon enter.

The agent looked at me sternly. A small Logitech webcam took my picture. I remember the brand because it was the same camera I used to Skype my then boyfriend ten years ago. The agent looked at me again and said my full name with neither favor nor disdain. “Yes,” I said with a too eager smile. He looked down at my passport and travel card, stamped them both, and directed me to the dusty beige door to my right. I turned the knob and breathed a sigh of relief. I had officially arrived in Cuba.

What to Expect When Visiting Cuba
What to Expect When Visiting Cuba

What to Expect When Visiting Cuba for the First Time

Whatever I expected — I was wrong about Havana. It’s a city of contradictions. The streets are full of trash but no roaches or rodents. The buildings are dilapidated but inside are layered in marble, murals, and mosaics from ceiling to floor. There’s graffiti everywhere but little crime. In fact, Havana is exceptionally safe. Late at night, families sit in the middle of streets on folding chairs, playing dominoes. The people are as interested in tourists as are the cats that roam the neighborhood. My two friends and I existed as locals, and the locals treated us as such. Someone would occasionally ask where we called home. “Ah, Chicago. Like Al Capone!” The mob had left their mark, and Havana is still in 1954.

The capital city is spartan, stripped down to necessities. It turned out the things we needed were more glamorous than anything we could create. We needed fresh air, rolling mountains. We needed to laugh, walk, move, dance. Mojitos? Need them too!

The island is cinematic, a sound stage of classic cars and Spanish colonial architecture.

“Excuse me, um…como, que… This street?” A tall white man walked up to my friend and me, pointing like an octopus and speaking gibberish.
“It’s okay. We’re from Chicago.” His face filled with shame. “Are you serious?” He pointed to a woman facing us, his sister. “We’re from Chicago too.” The Americans had arrived.

If you’re American, here’s some advice: Taste Cuba while you can. You’ll be better for it.

This month we’ll tour Havana and Viñales together, forgetting our troubles under the shade of a century-old tree.

Estás listo?

Photos: Kari Herrera for Chicagoings; La Guarida Restaurant in Havana, Cuba