WESTBROOK >> There was no moon visible on the night of Nov. 4, 2016 as Capt. Joy Sherman steered a 45-foot catamaran from Key West across the Florida straits. Gale-force winds and 15-foot waves rocked and battered the boat. In the dark night, tankers and barges seemed to come out of nowhere.
The owner of Joyride Charters in Westbrook had been hired by the New York City-based sailing club, Sailors NYC, to captain one of the three sailboats in a flotilla. If she could make it through the night, she and her seven passengers aboard, along with the 12 women on the two other boats, would be well on their way to becoming the first all-female crew to sail to Cuba.
But it wasn’t going to come easy, and not just because of the elements or the busy commercial shipping lanes.
“Key West was a new harbor for me to navigate out of, and on top of that it was nighttime,” she said. “Also it was a brand-new boat for us, and with the wind and waves, we were having trouble getting the mainsail up.”
That wasn’t the only unknown. Given that the sea gates to Cuba had reopened only a year before, “we didn’t know what to expect,” said Mary Ann McCruden of Freeport, N.Y., a seasoned sailor who acted as Sherman’s first mate. “We had no idea if we’d be welcomed.”
Amid the constant pounding, most of the passengers became sick. Sherman, too, felt a queasiness overtake her.
That was unusual for the Waterford native, who’s had her sea legs since she learned to sail and drive powerboats at 7, and was conveyed to school in a Boston Whaler. After college, she spent four years traveling from Maine to Florida and the Caribbean aboard large luxury yachts as a stewardess, chef and first mate.
She founded Joyride Charters as a leap of faith in 2004 after an 11-year stint managing different departments of her father’s car dealership. The business, which has grown steadily each year, features three-hour sunset sails, private lessons, and escorted charters in the Caribbean, including the Bahamas and the British Virgin Islands, each winter.
All that experience, though, wasn’t helping her on the night of Nov. 4, as she contended with buffeting winds and ships that seemed to bear down on her, and a nausea that wasn’t receding.
So the eminently practical Sherman, who keeps her day job working in Yale’s African Studies Department, contrived a mind game. She pictured “the act of taking a hat and throwing it over a fence, and following it. Every moment was like another hat over the fence.”
It worked. The sun came up. After a stop at Varadero, a beach community midway between Key West and Havana, they set off again. It wasn’t any easier.
“The wind was still howling and the waves were even bigger, 15 to 18 feet, so we were rolling all the way to Havana,” Sherman said. Equally challenging was the narrow entry into Marina Hemingway, where all foreign boats are cleared, according to McCruden.
“Joy handled it beautifully,” she said. “She just knows what she’s doing. Plus she has this amazing calm.”
Alighting on land, it soon became clear that the demanding 30-hour sail from Key West had been worth it.
“It wasn’t like a normal Caribbean country,” said McCruden. “Havana has the look and feel of a metropolis.” And with the colorful colonial architecture and the private houses with arcades, balconies and internal courtyards, “it also has this distinctive charm.”
“I felt like we were deprived of Cuba for so many years,” she said.
For Sherman, it was the friendly and humble people that made an impression. And the tour guides with their strong views on the U.S. election. (It coincided with their arrival.) Not least was the restaurant in a private home, called a parador, that overlooked Havana Harbor.
“People are trying to do whatever they can to make money and if they can get some kind of tourist business they can make extra money, and the food was fabulous,” she said.
Following an uneventful crossing back to Key West, there was no fanfare on their historic passage, but that was okay.
“We were all really proud of being the first group of women to navigate a boat to Cuba,” said Sherman, who is planning another charter there. “We all want to go back.”
Even without the public acclaim, she recalled with satisfaction the moment that the magnitude of what she and her crew were about to accomplish dawned on her.
She was on the floor looking at the instrument panel when customs officials came on the boat.
“They were asking ‘Where’s the captain?’ and everyone was pointing at me and one of them said ‘No, the captain,’ and they kept pointing at me. They couldn’t believe I was a woman captain and we were all women doing this.”
Joyride Charters, 63 Pilots Point Drive, Westbrook. joyridecharters.com. 203-530-5037. [email protected]
Lisa Reisman, Shore Line Times
January 31, 2017