On Nov. 4, Joy Sherman, an administrator for the Yale Council of African Studies, faced an immense challenge: captaining a sailing crew on a round-trip voyage from the United States to Cuba and back.

To complicate matters, her group had to depart in the middle of the night from a harbor filled with reefs and other obstacles that Sherman had never navigated before. But despite the elements posing constant challenge, Sherman and her crew completed the historic journey from Key West, Florida, to Havana and back, becoming the first all-female crew to accomplish the feat.

“She included all of us,” said Ginny Jaeger, a crew member. “[She] was the youngest one, but she was always inclusive and open to hearing anything. It was an awesome experience, and she made it great.”

An experienced sailor and the owner of Joyride Charters, a sailing company based in Westbrook, Sherman was hired by the sailing club Sailors NYC to captain a six-woman crew on the 106-mile trip from Key West to Havana.

While the distance to their destination was relatively short, Mother Nature did not facilitate a smooth trip for Sherman and her crew. Their catamaran was jolted by 15-foot waves all throughout the night and the constant rocking of the boat led to many of the crew members, including Sherman, getting seasick. The only visible light was that emanating from the large freighter ships populating the sea, which required constant vigilance to navigate. According to Jaeger, Sherman hardly slept at all throughout the night.

The one constant amid the array of challenges was Sherman’s steady and inclusive leadership. Mary Ann McCrudden, an experienced crew member who served as Sherman’s first mate, said she felt nearly unaware of the challenges facing the catamaran.

“I never even thought we had a difficult situation with the seas and the wind and the storm,” McCrudden said. “I never felt at all that I was ever in danger.”

Jaeger was just as effusive in her praise, explaining that Sherman prioritized safety and made all of the sailors, regardless of their levels of experience, feel included on the trip.
Under Sherman’s command, the crew arrived in Varadero, Cuba, after the sun came up. In passing through customs, the crew underwent an extensive search, with the officers fascinated by the Americans’ assorted sweets. The search was “business as usual,” according to Sherman, until one of the customs officers demanded to know where the captain was. Never imagining the possibility of a female captain, they could hardly believe their eyes when Sherman raised her hand, according to Sherman.

After the search, Sherman’s crew proceeded along the coast of Cuba toward Havana. The sailors had an opportunity to explore the metropolis, marveling at the beauty of the city while being struck by its evident poverty. Sherman noted the absence of cell phone usage when walking around the city, and how many locals looked her directly in the eye.

“[People in Havana] seemed so happy and sort of humbled, or innocent,” Sherman said.

Still, no amount of trusting smiles could hide the poverty present on the island. The group met a dockmaster who had to give up his job as an English teacher because he couldn’t make ends meet. They also met a military veteran, educated in information technology, who was relegated to selling tourist trinkets on the street.

Nevertheless, the majority of Cubans whom the crew met in Havana remained hopeful that American tourism would prove to be a boon for the newly reopened country, though they expressed overwhelming fear about the potential for the Trump administration to negate much of the progress that has been made between the Cuba and the United States, Sherman recalled.

After spending time on the island, the crew decided to head back to Key West during the day. Fortunately, the sailing weather was far better on the return trip. The crew not only witnessed a beautiful sunset, but also saw dolphins and other sea life along the way, Jaeger said. She described the return trip as being “so much more relaxing” compared to the choppy nighttime departure.

Sherman’s navigational skills would be tested once more, however, as day turned to night. Arriving at Key West at 1 a.m., the crew had to dodge the same reefs that complicated their departure. But Sherman passed the final challenge with flying colors, cementing her crew’s legacy as the first group of all-female sailors to successfully complete the round trip.

Sherman hopes to continue to build off of this experience by hosting a sailing trip around Cuba for Yale students next December.