On a sailboat named after another sailboat, which borrowed its moniker from an Eric Clapton song, Liz Gillooly stands at the helm of Layla, steering her gently back and forth and surveying the bay in front of her. The motor is on, helping her to maneuver the 45-foot mammoth in between anchored boats and docks, yet the 30-year-old moves it with ease, gliding along through the still waters.
Every boat is new [at first], so there is a learning period. But now this feels like the back of my hand.Liz Gillooly, owner and captain of Layla
As the sailboat heads for open water, the boat-speak kicks in.
“Rachel, you can go ahead and start throwing the line,” she said to first mate Rachael Bofinger. “Watch out for the boom if we start jibing or tacking,” she cautions the other people on board.
Bofinger starts up on deck and begins pulling at ropes and straps, adjusting the sail as it goes, then moves back toward Gillooly, the captain, who continues navigating. Bofinger turns a crank with a handle, filling the windy air with a constant clicking noise, until she stops and the sail is in the perfect position.
Gillooly turns off the engine with a switch and the only noise left is the wind getting caught in the sails and the Peconic Bay salt water lapping up the side of the boat. The two-hour sunset sail is part of a package offered by Gillooly’s sailboat charter business, Layla Sailing, where in the warmer months she and Bofinger take groups of up to six out for a sail. On this warm June evening, the two are just beginning their second season with the business.
Gillooly grew up on the North Fork, taking sailing lessons at Orient Yacht Club from the age of 8, but when it came to racing, which many young sailors transitioned to, she was not interested.
“Learning how to sail, I was immediately like ‘Let’s bring sandwiches and just like go off course and relax on a boat,’ because that’s always been my way of enjoying the water,” she said.
At 20, she took a semester off from college when she was offered a spot on a sailboat headed down to the Virgin Islands. One semester off turned into a four-year stint down there.
“I worked on different boats and worked my way up and got a captain’s license,” Gillooly said. “And I just sort of fell in love with the lifestyle.” Over the course of six years, Gillooly has sailed across the Atlantic Ocean as a first mate, spent a summer in the Mediterranean, been employed as a whale watching guide, and landed in Maui working on a catamaran. Four years ago, she decided to come home to spend more time with family while traveling all over the world in the winters.
“I got a job working on a sailboat out here as a captain for three years,” she said. “I was the captain of East End Charters. And then I decided to make the leap to buy my own boat.” That was last year. After spending three years searching on yachtworld.com, the Craigslist of yachts, Gillooly found her dream boat in Connecticut — a Fastnet 45 from the 1970s — and launched Layla Sailing in May 2019.
“It’s a lot of work,” she said. “There’s a steep learning curve with all the maintenance and stuff that I have to do now. But I love it.”
Working in the male-dominated sailing world, Gillooly sees her all-women team not just as her and Bofinger, but as all the women captains they have worked with before and helped them get to this point. Bofinger, an Orient native, grew up with commercial fishermen parents, and after buying a one-way ticket out to Hawaii to live, she missed being out on the water in her hometown.
“I bought a bunch of books off Amazon and read them the whole time I was down there,” the 27-year-old said. “When I got back home, I bought an eight-foot little sailboat. I took it out and I was like, ‘OK, I can do this.’ And then I bought a 14-foot sailboat.” She met Gillooly while both worked for East End Charters and then came on board to work full-time for Layla Sailing. She is currently working toward her captain’s license. Together, this two-woman company has done more than 100 charters in its first year.
“I think [women in sailing] is getting more and more common. I happen to think that girls do a better job,” she jokes. “It’s an eye for detail.” Those details can be seen all around Layla. It’s the fluffy throw pillows in the back of the boat, the plush bean bags up front and the trays they use to make cute charcuterie boards.
Another huge part of Gillooly’s business is giving back. She donates at least 1% of every dollar spent with Layla Sailing toward environmental initiatives.
“From the beginning, I felt like I wouldn’t want to start a business without giving back to environmental causes,” she said. “The reason we’re all out here is because we love being on the water, and I think preserving it is kind of what’s most important.”
She also gives back to local institutions like the Orient Fire Department, Cornell Cooperative Extension of Suffolk and Eastern Long Island Hospital and, most recently, is giving away a sunset sail to a hero during the COVID-19 crisis.
“That’s the stuff I care about,” she said, “This community has given me so much already.”
One of her most cherished sailing memories is going out on a family friend’s boat named Layla in Orient.
“That was the most elegant, beautiful boat and it always meant the start of summer,” she said. “And then, when I bought a boat, our friend had just passed away, and it seemed like a good tribute to him and that feeling of summer.”