What to do and where to go from the captain of Greenport’s women-run charter, Layla Sailing
Liz Gillooly learned the fundamentals of sailing at the Orient Yacht Club at just 8 years old but considers herself a “sailing school dropout” because of her indifference to racing. But her yearning for adventure and meaningful experiences is what led her to commanding a successful, women-lead boat charter business: Layla Sailing.
At 19, she was working a summer job at Scrimshaw Restaurant in Greenport when one day, a boat crew asked if Liz wanted to join their voyage from Greenport to the Virgin Islands. She couldn’t say yes fast enough.
For four years in Caribbean paradise, she worked on different sailboats and earned her captain’s license. Once she left the Virgin Islands, Liz further strengthened her sea legs as a first mate on a 116-foot catch rig sailboat traveling across the Atlantic Ocean for 25 days.
She spent the summer in the Mediterranean, became skilled in larger yacht maintenance and then moved onto her next job working on a whale-watching excursion in Maui, Hawaii.
Liz’s home has always been at sea, but after years of travel, it was time to return to the waters of her true home on the North Fork. She also embarked on the journey of buying a sailboat.
“I found Layla on Cape Cod and sailed her down at the end of November on a freezing, cold day where the weather was not what we expected,” Liz recalled. “We were soaked from head to toe, the whole way down the 14-hour sail, and then she was here—I got to do some work on her, fix her up and now I’m in my sixth year of sailing with Layla.”
In a male-dominated sailing world, Liz and her crew are breaking glass ceilings. With all the sailing secrets she has acquired from her travels, Liz mentors the next generation of female captains.
“I have been super fortunate that over the years, I’ve been able to train crew and right now, I happen to have an all-female crew, which is just so special,” Gillooly said. “I was brought up through this industry by a lot of women captains who sort of gave me an opportunity that I maybe wouldn’t have had—it’s been great to be able to mentor some of these young women.”
These are Liz’s favorite North Fork things:
Favorite place to sail
My favorite place to sail on the North Fork is Gardiner’s Bay. It’s just whenever I’m on a charter, I love taking people out past “Bug Light” (Long Island Beach Bar Lighthouse)—which is the lighthouse that sort of leads right to the entrance of Gardiners Bay. It just opens up when you get there and you’re in between two Forks. It reminds me of some of my travels and being out in the Caribbean. You can see the vastness of being out at sea.
Favorite beach
Truman’s Beach in East Marion and I love Pipe’s Cove in Greenport.
Favorite sunset views
My favorite spot for sunset views is on the deck of Layla, but from land, Truman’s Beach, again, is one of my all-time favorites as a place to go.
Favorite seafood spot
Little Fish (50 North Sea Drive, Southold) is one of my new favorites, we go there all the time. The Southold Fish Market (64755 Main Road, Southold) also has great snacks—they have everything, and the seafood is incredible.
Favorite thing to do with guests during a charter
Having people jump off the boat to go swimming. We have this big, blow-up inflatable toy called a Sunchill where people can float around, sit in a circle, and just chat and relax. I love to watch people be able to melt into the relaxation of being away from everything, all their responsibilities and just embrace the moment.
Favorite women-owned business
First and South (100 South St., Greenport) is one of my favorite restaurants in general and Sarah Phillips Loth who runs it is incredible. The North Fork Art Collective (207 Main St., Greenport) run by Kara Hoblin, is a wonderful gallery and so beautifully done—everything she does is amazing. I get my hair done at Craft Hair (213 East Front St., Greenport), that’s wonderful woman-owned business. Also, Steph and Elizabeth of Little Ram Oysters Co. (61600 Main Road, Southold) are both amazing women.
