A chartered catamaran sail in the Caribbean off Cuba.

Written and photographed by Linda Grasso

I am not a boat person. The last time I hit the seas I was pregnant and vacationing on the island of Lanai. My most vivid memory is of the boat’s captain pressing cold towels to my neck.

Nevertheless, I signed up for a voyage on a 41-foot catamaran with four cabins, in the Caribbean Sea off the southern coast of Cuba, with my husband and son. We would be part of a flotilla of five families—all from the LA area.

Also my husband and I wanted to spend time with our 20-year-old son. Ever since he started college, he’s pleaded, “I just want to sleep in my own bed.” When he shocked us with, “That sounds like a cool trip!” we jumped on it. (Five days of having him all to ourselves—no electronic devices and I’ll just say it—no girlfriend—was just too lovely to refuse.) We thought our younger son could also join us but then discovered he didn’t have enough school vacation. Should we cancel? We decided to go for it.

Day 1
After an hour-long flight from Miami, we arrived in Cienfuegos, a small city on Cuba’s southern coast. As our group hopped aboard a big charter bus, I popped a motion sickness patch on the back of my ear, and we were off to the marina.

The afternoon was spent in a flurry of activity. Some families arrived to a boat stocked with food; others needed to buy provisions. Some of the captains spoke English; others did not (ours thankfully did). Then came lots of fee paying and document showing. Apparently Cubans are not allowed to charter boats for fear they will flee to America.

We enjoyed dinner at a local restaurant. As evening fell, a large patio was transformed into a dance floor. It was Saturday night. Young and old—and everything in between—made merry. They danced and chatted together in a mixed social scene rarely seen in LA.

Day 2
I slept in. Our crew, however, had been up since 6 a.m. embarking on the eight-hour, 55-mile journey to Key Largo. I was grateful that by the time I woke up, we’d passed through the deep, rough ocean waters and were in more shallow, calm, emerald- blue waters.

During the sail, the captain ran two fishing lines. Alerted to a catch by the shrill, whirling sounds of the line, he flew into action. We caught one yellowtail and three barracudas. The crew followed the Cuban custom of pouring rum down their throats “to ease them into death.” Apparently there is no PETA there.

We anchored for the night and took a dingy over to a friend’s boat for a cocktail and a salsa lesson from the crew. Later we feasted on fresh lobster prepared by our cook, Corona. Afterward I asked him what I should buy when we arrived in Havana, besides rum and cigars. He responded, “Forget about that. Walk the streets and interact with the people. That is how you experience Cuba. Touch our soul and that is how you will remember Cuba.”

Day 3
We sailed to a nearby reef for snorkeling and then docked at Key Largo where we found a few small open-air restaurants and inns. One of the four catamarans did not show up. We had not seen the crew since setting sail from Cienfuegos and thought they were just doing their own thing but—at this point—we started worrying. After a couple of stressful hours, the missing boat showed up. Turns out they’d had engine trouble and were stranded on rough seas overnight. We were concerned about getting their boat repaired so they could continue with the rest of the journey.

While that mini-crisis played out, we took a dingy to an even smaller island with nothing commercial on it. We found more gorgeous shells, including football-size conch shells with raspberry interiors and a myriad of large starfish that ranged from gold to maroon. There were iguanas all over. That evening, we enjoyed an amazing sunset.

After another lobster and fish dinner, the young and old on our trip (there was nothing in between) rocked out to music on our catamaran. Some of the teenagers were not familiar with the music of Bruce Springstein (not ours!). Suddenly in the midst of dancing on a chair with my son, I realized while in Cuba, we were doing like the Cubans.

Day 4
We awoke to good news. Our friends’ boat had been repaired. After a planning meeting with all the boat captains, aimed at keeping our flotilla intact for the duration of the trip, we sailed to Paradise Beach on Key Largo. We explored—and exfoliated. The pearly white sand, as the spa aficionados on the trip discovered, was terrific for a full body exfoliation.

While snorkeling we discovered a sunken ship, beautiful purple coral fans, tons of brightly colored fish—as well as stingrays. When one slid by me about two feet away, remembering the Crocodile Hunter/Steve Irwin story, I hightailed it back to the catamaran. I had no idea I could swim that fast!

Day 5
We spent a gloriously relaxing last day. I’d had a ball, but to be honest, I was ready to get off the boat (and head to the next leg of our journey, Havana). I was also ready for real bathroom facilities. (The toilet? I won’t go there but the shower was basically a sink faucet that pulls out.) And I was definitely looking forward to some different cuisine. Every entre seemed to have the same sauce (I’m pretty sure the base of it was catsup) and was served on white rice. We only had veggies once.

That said, it was an exhilarating experience. For the most part, my motion sickness remedy worked and I found being shut off from the world deeply relaxing. I’ll always remember the scenic, pristine beauty of those islands and the chance to spend quality (unplugged) time with great friends, my husband and, most of all, my son.