Bicycling in Cuba—Take Two—February 2026

I am playing the accordion again; chest full of bravado and excitement one moment and clenched tight with worry the next. I am returning to Cuba again, this time to bicycle from Santiago de Cuba in the East, lengthwise to the western tip, but this time alone.

Well, that is not true. Not only will I be surrounded by the kind, forgiving and generous people of Cuba from day one, but I will also be joined halfway through by two friends in Havana. Two fellow Mainers, who will continue on with me and complete the western loop portion of the ride. The bicycle tour will cover 1,000 miles in entirety, I hope.

I was torn about returning to Cuba this time and vacillated to commit due to the actions of our current president and administration. The writing is on the wall in regards to the effort he is making to overthrow Cuba by making life there untenable. He is blocking needed oil and implementing tariffs that will effectively starve the already struggling country.

At first, I was selfishly worried about my own safety, but then I began corresponding with few people in Cuba and was told repeatedly that struggle is what defines Cuba.

“When have we not struggled? Come, we need people to come.”

“Don’t let fear mongering rule. That is part of the plan; to scare people away. We live here, it is the same. We make do.”

“You will be fine. It is only the Cubans that will suffer.”

So, I bought a ticket, got my visa and packed my bike. Now, I just worry about missing my family and how sore my bum is soon to be. I know food will be scarce, as well as electricity, but I feel comfortable in that situation now after so many bike tours. In fact I actually look forward to dabbling with having less. It makes life seem clearer. I live in relative opulence and I have a tendency to become a bit too comfortable. Within that comfort, I feel like I can start to lose my way. This time I intend to share as generously as possible.

Again, I will stay in Casa Particulares which are individuals homes, and steer way from resorts and hotels. I like to be immersed.

I will post when I can. I am incredibly lucky. I leave Thursday.