Bicycling around Cuba 2026–Day One

Last night I bedded down on the floor of the Miami airport, in the hallway above D15. It was loud, bright, cold and hard as cement—literally. Some might say perfect sleeping conditions. There were a few other fellow travelers lined up along the corridor, letting go of all noble pretenses, and wrapping themselves in blankets of jackets, open mouthed drooling onto their luggage that doubled as pillows. 

I was no better. I nestled into my sleeping bag liner that I bring with me when I travel, just in case the sheets somewhere are simply too nasty. I wore a fleece jacket with a hood cinched up around my head and cocooned  myself entirely. I am sure that the liner looked like some sort of body bag that made it appear like I was an abandoned corpse.

During these times, I try not to think lest I fall into despair about choosing to leave my cozy bed and loving family behind. Instead I find walls going up in my mind, allowing me only to think about immediate needs. Sleep. Lucky for me it happened.

Now I am on the plane, heading to Santiago de Cuba. There are very few people speaking English and I think that is a testament that tourism is way down. The town where I am starting my ride is along the south-eastern coast. It is surrounded my the Sierra Maestra mountains, the tallest mountains in Cuba. It is known for being riotous and rebellious; this is the area that Castro’s revolution took hold. 

I hear there is excellent music and a vibrant art culture, but there has also been a terrible hurricane this year and there is no longer reliable electricity. I think the instability is keeping many away.

For some reason,  I am not nervous anymore. It seems like the leaving is the hard part for me. I am feeling ready. Now the adventure can unfold.