This is the first post in the story of my family’s trip to Cuba. The secret, mysterious land just off our coast has been one of the few places closed off for Americans. And when you suddenly tell Americans they can now go somewhere they couldn’t before, it becomes a lure, a top-of-the-bucket list desire.
For my parents and me, it was a free cruise we had been given as a result of the ship/tanker crash we survived last summer while visiting Greece and Turkey. As we boarded that very same but now fixed ship in Jamaica, we were a bit wary but noticed a few upgrades, including the deck off our nice room. The food still was not so great and the cruise line’s staff and crew were disorganized, but almost everyone was very pleasant and kind and willing to serve with a smile.
My trip started off at an ungodly hour for me on December 24. I paid for a seat upgrade so I could get on early and sit in an exit row with some more room. But with some “turbulence” occurring near our Hub destination we sat and sat and watched the clock go past our now missed connections. Finally arriving in Charlotte and winded from a sprint to my connection gate, I headed back to the help desk and was told I missed the last flight to Jamaica. Fort Lauderdale and a lonely Christmas Eve was in my near future. One of my favorite hours of the year are usually spent with my family in Christmas Eve services so this vacation was starting out not so good.
Another super early morning got me on a very empty flight to Montego Bay where I landed safely and met my parents at the port. We had a nice Christmas day afternoon on board in our old boat—hoping we would avoid any collisions his time.
Our trip was scheduled to take us to Santiago, Havana, Maria de la Gorda, and Cienfuegos. Overall, the trip was interesting, the seas were really rough, and we ended up sailing past Guantanamo at night and going all the way around this very large island nation (or more accurately, this archipelago of islands nation).
The Cubans are just getting ready to become a destination for tourists. They have a lot to do to prepare for a rush of Americans (if they want to keep up the tourist trade from our countrymen). The lack of Internet access, luxury hotels, and more organized tours and sites won’t live up to most standards in the long run but at the moment the mystery of the destination and having the cruise boat as a home, provided the comforts the first adventurers need. We overhead many people saying they were glad to get to Cuba before the Americans came and ruined it.
Many people envision Cuba as a place out of time. I would say that is somewhat true. The cars are vintage for sure and there were lots of people using horses as transportation, but beyond that and the items found at their “flea markets,” it was very much like visiting a somewhat poor Caribbean country. When the Soviet Union ended, so did the rich support Cuba was getting. And while they have excellent health care and a nice education system, most people are poor. But not necessarily unhappy. The politics are complex and we got a balance of truth and propaganda—certainly seeing the “evil” portrayal of American politicians and the CIA and their hurtful policies during and after the revolution.
I was surprised at the overwhelming presence of books, postcards, monuments, etc. of Che Guevara. Of course the people can’t speak out against him but on the surface the memory of him is honored and celebrated everywhere. He was a monster in disguise and has a most impressive PR agent—in the form of El Jefe himself who is sliding into history as we speak.
The people were nice and it was a pleasant experience getting to know their culture—a mix of native Indians, Spanish, and Africans who have combined their cultures to form the unique culture that is now Cuban.
Next post, I’ll talk about our first port stop in Santiago.

Colorful buildings dot the streets. Some are slowly being renovated and some falling apart. A slow process.
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