Pineapples have long symbolized hospitality. Legend has it that sailors would spear a pineapple on a fence post to symbolize their safe return, but the spiky fruit also served as an open invitation to come celebrate. In Orlando, pineapples are also a symbol of endurance. “When Orlando’s citrus was completely wiped out by the Great Freeze, pineapples remained,” says Carol Holladay, owner of The Pinery.
Hospitality and endurance are fitting symbols for Holladay. The ebullient entrepreneur who returned to her native state after living in Charleston, South Carolina for many years, was set on opening a restaurant where the community would feel at home. “In Charleston, everything is about celebrating the Lowcountry. I thought to myself, ‘Why isn’t anyone celebrating Florida?’"
Her path to The Pinery, named because it’s located on what was once the largest pineapple farm in the United States, wasn’t without its bumps. The building housing the restaurant was a beloved funeral home. “[It] had been here since the 1950s (it was on the Historic Registry) and with the new buildings going up, the neighbors were upset because they were watching their community change. I listened, and thought, ‘Let’s make this a win-win.’"
Holladay set about turning the restaurant into an homage to old Florida. From vintage postcards and antiques, to reproductions of historic signs, the dining room is a treasure trove of a bygone era.
While the look may harken to the days of old Florida, the thinking is positively fresh, new, and female focused. An all-female executive team was built with Beverage Manager Nicole DeLucia-Barney and Chef Naomi Freeman running things. “I wanted an all-female team here,” says Holladay. Indeed, female influences run rampant and cross generations. “When Naomi walked in, I learned that she was from the same part of Florida where my grandmother was from and where I spent a lot of time growing up,” she says. “It was serendipitous.”
Therefore, the trio looked to their own families for some of the food and beverage offerings. The menu takes cues from Chef Freeman's mother incorporating some of her recipes and De-Lucia Barney paid homage to Holladay's grandmother with a signature cocktail (others are named for historic Orlando touchpoints). The influence even extends to the restaurant’s interior design, which showcases pecky cypress salvaged from the home of Orlando’s famed entrepreneur, Lisa Hawley. “I love feeling that energy,” says Holladay.
Still, like the pineapples that survived the freeze, Holladay too has endured a set of challenges, including Covid-19 and a breast cancer diagnosis. She's also overcome the naysayers who thought she and her team would fail and others who think her time would be better spent home with her children.
The ever-positive Holladay shrugs it off, preferring to admire the golden glow of a full dining room on any given night, knowing that she’s contributing to her community. “I created The Pinery to bring a sense of self to a community that felt they were losing that. I want everyone to feel special when they come here—that’s why we built this place.”
Hero image: Lindsy Hardin-Deal/The Pinery
All photos courtesy of the Pinery
