An Incredible Trip to Cuba as “Skipper Americana”

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One day, after delivering a boat to the 31st Street Marina in Chicago, I ran into Bruce, a super cool, retired pilot, captain friend of mine. While we were chatting it up on the dock (where all good plots are hatched), he said “Hey, a bunch of us are planning a trip to Cuba this winter. You should come.” Who would say no to that?? Fast forward a few months and this eclectic band of wonderful people were off on a grand adventure.

The Cast of Characters

Trip to Cuba Goldfish Poker

Playing Goldfish Poker aboard the Piropo.
Photo courtesy Shelly Galligan.

The cast of characters also included Bruce’s wife Amy, a drop-dead hysterical, crusty ER nurse, card shark and kindred spirit; Greg, an uber smart, techy, can-do guy who’s cool as a cucumber and the definition of grace under pressure; Kate, dingy racer turned big boat sailor, world traveler with a heart of gold, and fluent in Spanish!; Noel, a triathlete and strong, silent-ish type. Taking it all in and photographing it for posterity: Diana, a nurse practitioner, free spirit, enlightened dancer of the salsa; Susan, a tough-as-nails Chicago cop with a warm chocolate chip center; Johnny, an infectiously bouncy, happy, stamp collecting, retired teacher turned Zumba instructor and poet laureate of the boat. Think Tigger; and one whiny complainer in that “every party needs a pooper” kind of way.

This amazing band of soon-to-be adventurers made our way from different parts of the Midwest and gathered in Santa Clara, Cuba, to explore for the first few days. While on land, we stayed in hostels, Cuba’s equivalent of a bed and breakfast. Our hosts provided cheese, fruits I had never had before, and plates piled high with yummy toast. We were especially grateful as the abundance of food we enjoy in the U.S. is not the case in Cuba.

A Step Back in Time

Trip to Cuba Timewarp

A Trip to Cuba truly is a step back in time…
Photo courtesy Shelly Galligan.

We’ve all heard that being in Cuba is like taking a step back in time. This is absolutely true. It’s an amazing, diverse mix of beautiful architecture, gorgeous old cars, and stark reminders of revolution and politics. There are no signs of wealth or privilege to be seen. Cuba’s richness lies in tradition, beauty and the warmth of her people. I felt very welcome, though blond hair and fair skin were something of an oddity in Santa Clara. Several older people looked at me with wide eyes and asked to touch my skin and several young men tried to teach me how to salsa dance. Little known fact, Galligans don’t dance. Even salsa dancing Diana couldn’t make it happen for me.

We explored Santa Clara on foot and by pedal cab. Up and down city streets, through the town square, museums of the revolution, and an outdoor tchotchke market. There are a few restaurants and through Kate’s stellar Spanish skills we were able to unearth the local favorites.

From Santa Clara in Central Cuba, we headed to Cienfuegos on the Caribbean coast. There was an issue with the service we had arranged to take us to Cienfuegos so the hostel owner made arrangements for someone he knew to take us. This turned out to be a delightful alternative. Our driver was wonderful and shared so much fascinating information about the country and life living in it. He’s a musician and his father a physician. We were all such a great match, he agreed to return for us at the end of the charter to take us to our next destination.

There was a smidge of waiting involved for the boat to be ready which we used to explore this charming coastal city. We took a horse drawn cab into the center of town. The horses in Cuba are very skinny with sharp bones visible right through their hides. There also seems to be only one breed of dog. My running shtick was that there’s only one dog in Cuba and he really gets around.

The Catamaran Piropo

Trip to Cuba Piropo Safety Meeting

Holding a safety meeting aboard the Piropo.
Photo courtesy Shelly Galligan.

At some point during the wait, I wandered out to the boat to take a peek. There was a tall, dark and handsome man changing the oil. I asked if it would be okay if I observed the process. He looked at me like I had three heads and went about his business with a dismissive look. Undeterred, I watched the process then returned to the Marina for our navigation meeting with the charter people.

When we were able to take possession of the boat and move aboard, tall, dark and handsome (who’s name turns out to be Michelle) showed up with his clipboard and checkoff sheet to orient us to the vessel, the catamaran Piropo. He wanted to address the captain and looked at one of the guys who shook his head. He looked at another who shook his head and pointed at me. He looked at me and as it dawned on him he said, “Noooo” with some disbelief and a shake of his head. I said, “Oh, yes” with a nod of mine. One more “Noooo” and an “Oh, yes”, then profuse apologies started to pour. I’ll admit it was a pretty great moment for me.

After we stowed our gear, got the galley in order and figured out how to get the chart plotter from German to English, we set off toward our first overnight destination. Cayo Guano is a tiny island, uninhabited except for a lighthouse and keeper’s quarters.

Señora Capitana

Skipper Americana's Trip to Cuba

Señora Capitana.
Photo courtesy Shelly Galligan.

The next morning we were off to Cayo Largo via a stop at Playa Sirena. Once anchored at Playa Sirena, Greg, Kate and I snorkeled to shore for a beach walk. There were strange tracks all over the bottom of the ocean here, like the lunar module had been popping wheelies all over the place. We eventually figured out they were conch tracks! There were hundreds of them in this pristine place. We referred to them as Fidel’s conchs going forward.

While walking on that beach we happened upon another Cienfuegos charter, captained by a Cuban man from the Marina. They were anchored in a protected little cove. He and Kate got to chatting about sights we should see and she told him I was the captain. Word had apparently traveled ahead of us and I was greeted with a reverent, “You are Señora Capitana?!” Apparently, there aren’t many women captains in Cuba. The looks of incredulity I received from the charter people, other captains and port authorities along the way were absolutely wonderful. I loved my fifteen minutes of fame!

By the time we got to the marina in Cayo Largo the breeze had really picked up and we docked in challenging conditions. The Port Captain and the Immigration Officer came aboard to check us in. Again with the raised eyebrows! In light of the Señora Capitana thing, the Port Captain told me that in Cuba the man always has the last word in his house and asked if I knew what that word was? “Yes Dear!” He then gave me a tour of the area and a complimentary umbrella-ed beverage in honor of Internacional Dia de la Mujer. Forty knot breezes kept us holed up on Cayo Largo for several days. Señora Capitana became Skipper Americana with the familiarity. We kept ourselves busy with umbrella drinks, cigars, and sightseeing excursions on land and by the dingy. The mojitos in Cuba are second to none.

The Trip to Cuba Turns Sporty

The day before we were to head back to Cienfuegos, the wind started to blow the floating docks off their anchors. It was time to bug out as an evacuation of the docks was ordered. Checking out of Cayo Largo involved taking everyone’s passports to multiple offices. At the last office, there was a very commanding woman in charge. When I walked in, she snapped her fingers and three men jumped to their feet and offered me their chairs. It was amazing! That task finished, we shoved off the struggling dock, headed back to a cove on the inside of Playa Sirena and found a spot amongst the throng to anchor for the night, with a planned departure back toward Cienfuegos the next morning.

If anything, the wind increased in velocity overnight and we had a tough decision to make. We either had to make arrangements to have the boat picked up at a significant cost or get it back to Cienfuegos in big wind and waves. We discussed the situation at length, checked weather forecasts and local knowledge and made a decision to poke our noses out and try (after passing out a few doses of meclizine). The wind was smokin’ and the waves were big. They were the kind of waves that when you’re in the trough, you can’t see anything but water all around. Noel did his best to get photos, but they couldn’t do the waves justice.

The beautiful Piropo did her job. She handled the waves with grace and style. It was sporty for quite a while, but the wind did eventually settle down and the sailing was wonderful. We arrived back at the marina in Cienfuegos safely with Michelle still apologizing!

Trip to Cuba? Totally Worth It

Once back in port, our driver from Santa Clara was waiting to take us to Trinidad, a UNESCO city, to experience more of this stunning country. Trinidad was charming and lovely as were the people we met along the way. The artwork, architecture and music made my heart happy. I “might” have bought a box of Cuban Cohiba cigars from a guy. Another hostel, another wonderful experience, then sadly back to Santa Clara to leave this beautiful country. Our driver gave each of us a parting gift of homemade peanut candy and a CD of his music. The amazing people we meet while traveling are the very best part. I spent a little time in the “naughty room” in Customs on the way home, and I’m on TSA’s Global Entry s**t list, but it was totally worth it.

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