© Patti Hartman

“There has never been a time in my life where boats were not part of it,” says Joy Sherman, the owner of Joyride Charters in Westbrook, CT. “I lived in Gales Ferry, CT until I was 8 years old. My father had a boat in the Bahamas, and we lived on her when I was 6 and 7. I did some schooling in the Bahamas, and with lessons sent by mail from my teacher at home there were classes on the boat as well. I remember sitting in the main salon and crying that I had to do schoolwork! When we left the Bahamas, we lived on the boat in Miami and I was driven to school in our tender, a Boston Whaler.”

“As a kid I observed a lot,” Joy recalls. “My dad had very high standards for the upkeep of his boats, and they were immaculate. He had people that worked on his boats and I watched how they did things. I had a friend in elementary school whose family had a Blue Jay at Thames Yacht Club in New London. I remember sailing with her a lot and learning a lot on that boat. There was nobody observing if I screwed up. We had a lot of fun on that boat! One time we sailed it to Fishers Island. It took all day, and we only we had time to put our feet on shore and jump back in the boat to sail home.”

Joy earned her BFA in Photography at the Rhode Island School of Design. “I was doing photography for an interior designer in Providence, but the work was not steady. When the America’s Cup came to Newport, I met the crew of a 110-foot converted hospital ship called Global Star. They needed help serving drinks and meals to charter guests. My photo business was starting to do OK, but the opportunity to be on the water every day with guaranteed pay and tips was too good to pass up. I worked the entire summer aboard that boat. That fall, I moved to Florida and worked on several large charter yachts. I traveled the Caribbean, mostly as a cook, then first mate on a 60-foot Hatteras.”

Joy, who lives in New Haven, CT, launched Joyride Charters in 2004. “I was working full time at Yale University and didn’t envision the ability to work on the water. I had a U.S. Coast Guard Master 100-ton license, and my dad wanted to know what I was going to do with it. He was persistent, and found a 35-foot Pearson Alberg for sale in Essex. To appease him, I reluctantly went to look at her. I remember standing in the cockpit thinking, ‘Could I really do this?’ I decided to dive in. My dad, an impressive negotiator, made the deal with the owner, and I paid for her. I spent all winter creating my own website, designing a logo and business cards, and soliciting my new business. Years later, I sold Hado and bought a Catalina 36, Pure Joy. She’s super comfortable for charter guests.”

Joyride Charters offers afternoon and sunset sails on Long Island Sound. “You can sit back or take the helm,” says Joy. “Many times people have never sailed, and I love to get them behind the wheel. They’re usually hooked after that! I also provide lessons, on my boat or yours, and also help couples learn to work together on boats. It’s a smart thing to do if you’re a new boat owner. I’ve had couples tell me I saved their marriage.”

Pictured with Joy is Scupper The Boat Dog (his Facebook name). “Scup is a rescue dog and the first mate…well, really he’s the boss!” she chuckles. “While I get the boat ready for charters, he waits on deck for the guests to arrive. While sailing, he loves to cozy up to the guests. He’s made an amazing addition to my business and my life.”

“I’ve chartered boats in the Caribbean for twenty years, and added the global chartering division to the business about six years ago,” says Joy. “I charter boats in locations around Europe and the Caribbean, then sell the bunks. Thankfully, I’ve been able to fill boats rather quickly, sometimes adding a second and third boat and hiring local captains. I have a first mate aboard all charters, and passengers are encouraged to help manage the boat with rotating cooking of meals and sailing the boat if they like. We’re headed to Greece in October (depending on COVID), then Thailand in January. When the travel world opens up fully again, I’m planning to go back to the Grenadines, Cuba, Croatia, and Greece.”

In 2016, Joy was hired by Sailors NYC as captain of a 45-foot Fontaine Pajot catamaran, part of a three-boat flotilla comprising the first all-women crews to sail from the U.S. to Cuba. “It was an amazing voyage,” she recalls. “The weather wasn’t ideal when we left Key West at 11pm for the overnight sail, and we had strong winds, high waves, and multiple commercial vessels transiting the Gulf Stream all night. I didn’t expect Cuban men to be so surprised to see a woman captain. Women don’t run boats in Cuba, and they stood on the dock with their mouths open. Having an all-women crew was fantastic, and it was a wonderful and proud experience.”

“At this time in my life, there are many wonderful sailing moments both present and past,” says Joy. “As soon as the sails go up and the engine goes off, I’m transported to a collective memory of why I’ve always loved sailing.” ■

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