I first heard about Capt. Liz Gillooly in 2016 from my cousin while working three jobs in our shared hometown on the North Fork of Long Island and living with my parents to save money for a boat.
But despite being the same age and growing up only 13 miles apart, Liz and I never met until 2021. While I slung breakfast sandwiches for tips, started my esoteric sailing blog, and perused Craigslist for old sailing yachts, Liz was already a licensed captain, her Catalina 22 sat on a trailer in her parents’ driveway while she was in Africa, and her own sailing blog was peaking.
Although she may not admit it, Liz was a pioneering sailing blogger and travel writer with her website “Moxie & Epoxy” (moxieandepoxy.com), which she started in 2013. Professional, practical, and self-directed, Liz taught herself search engine optimization and quickly monetized her blog to live the life of a digital nomad, traveling and blogging from around the world.
Though she started sailing at 8 years old, her yachting and blogging career began accidentally when she postponed college for financial reasons and took a year to travel in Central America. She returned to the United States, finished a year of school, and landed an unpaid crew position on an 80-foot maxi yacht from New York to Sint Maarten. Captivated by the voyage, Liz stayed in the Caribbean for nearly four years, working charters with mostly other women captains and crew and earning her USCG captain’s license.
From the Caribbean, Liz made her first transatlantic and Mediterranean cruise as the first mate on a 116-foot ketch. Then she moved to Hawaii to work as a day charter captain and solo hike Kauai’s Napali coast before returning to New York. Her next command was with a charter company on her home waters and in her local yacht club’s dinghies where she taught sailing.
Between sailing seasons, Liz was travel writing and blogging in Africa, Asia, and Central America, being featured on early multimedia travel networks like Matador and travelcontinuously.com, and in sailing media such as Ocean Navigator and the Boat Radio podcast.
When I finally floated into Liz’s homeport in 2021, she welcomed me into Sterling Harbor in Greenport, New York, where, since 2018, she has owned and operated her charter business, Layla Sailing, aboard a gorgeous Fastnet 45. Designed by Bill Luders, Layla emerged from the LeComte yacht yard in the Netherlands. Liz hired me for day work helping to button Layla up, as the charter season was now over. I was intimidated as I paddled my falling-apart kayak up to the licensed captain with all her sea miles and her beautiful yacht, but my insecurities melted away as soon as she welcomed me aboard. Liz is passionate about supporting other women sailors. We banged out cotter pins, flaked the sails, and secured the hull and rig to be hauled out the following day. Since the designer of my boat, Bill Tripp, also had designs come out of LeComte, we declared ourselves “cousin ships”—after all, my cousin was the only reason we met.
Liz is passionate about having an all-women-run small business and crew, having seen the gender disparities in the yachting industry. In the future, she plans to sail Layla to the Caribbean for winter work, but for now, she is quickly becoming the yacht charter of choice for hipsters and New York City’s urban professionals.
Recently elected a town trustee in Southold, Liz also serves as a member of the steering committee for the Southold Justice Review & Reform Task Force. She’s determined to create opportunities for women and focus on water rights through her venture into local politics. Along with her seamanship, what’s most impressive is Liz’s deep entrepreneurial and political knowledge and how it intersects feminism, anti-racism, and climate justice. I’ll never forget standing around with some community members at the marina after working on Liz’s boat, and someone made an insensitive remark. Capt. Liz put her arm around the person’s shoulder and explained with love why it was harmful.
After we met, Capt Liz left the harbor to take Layla to the yard. We waved and took a picture of each other’s boats from our respective cockpits. I was also off the next day on a longer voyage south, so our time together was short. But I trust and hope I will sail with her again.