Roberta DePiero has spent her time in Key West collecting things: sponsors, scholarship funds, thousands of photographs, and even bags of trash picked up along Key West roadsides and beaches. Ultimately, it fits under one description: someone who shows up.
She arrived in Key West on something of a whim. A February 1991 vacation from Cleveland to visit a friend turned into a permanent move that April, landing her first job on the Schooner Appledore. “I could sail, be on the water, and be tan all the time,” she said of the appeal.
Now Roberta has been following her opportunities, inspiration, and heart on the little island at the end of the road for 35 years.
Her business, Key West Playbills, marks its 20th anniversary this year. It began after DePiero left five years of selling radio ads and was tapped to sell program ads for the Waterfront Playhouse. One theater led to another, then many more. She teamed up with long-time collaborator Peter Arnow and soon the two were selling ads across 17 different programs. “It’s been a great business,” she said, “but it’s kind of amazing to me that I’ve been doing this for 20 years.”
She’s equally known these days for Plogging the Keys, the litter-pickup effort she didn’t start but has been committed to shaping into a prominent community fixture. Friend Dee Dee Green launched the program years earlier; DePiero joined during the pandemic and now has helped grow it from a handful of regulars into gatherings that draw more than 65 people — helped along, she admits, by hosts who provide free breakfast treats at the end.
That instinct for turning small efforts into lasting institutions shows up throughout her life. As a member of The Sons and Daughters of Italy Key West Lodge #2436 she helped rebuild a membership base that had dwindled below the state minimum after the pandemic by organizing wine tastings, special events and a film series with the Tropic Cinema that raises money for the lodge’s scholarship fund for high school students of Italian descent.
A second-generation fundraiser and event planner, “it comes naturally to me to plan, execute and make things fun,” she said. She has organized and led any number of projects, and while even though by her own admission, “was never really what you’d call a poetry enthusiast,” she took the helm of the Robert Frost Poetry Festival, and with a mission to attract a broader audience, staged events like “Pirate Poetry” readings at sea and percussion-backed live readings with local musicians.
DePiero’s other lasting contribution to Key West is visual. She is co-author of two photo books: “After Life – Images from the Key West Cemetery,” published in 2014, and “Isolated Island – The Key West COVID-19 Spring of 2020,” a 300+-page collection featuring the work of 26 local photographers documenting the island from March 1, 2020, when Florida’s first COVID-19 cases were announced, until June 1, the day after the Florida Keys quarantine checkpoint was dismantled.
The project began with DePiero and friend Jody Gross riding bikes and photographing what they encountered; it grew, with collaborators Carol Tedesco and Eric Grahl, into a fundraiser that ultimately raised more than $60,000 for the Sister Season Fund. “I’ve never done anything that big from just a small idea,” she said, calling it the achievement she’s proudest of.
Photography is a vein that runs through nearly everything DePiero does. What began with volunteering to photograph headstones for Find A Grave requests turned into her becoming a chronicler of the island’s civic and cultural life — the Pet Masquerade, Nutcracker Key West, Red Barn Theater and Fringe productions, fundraisers and events of every kind. “I go back and look at pictures I shot in 1991 or 2000,” she said, “and I see people who are no longer here. It’s part of my genealogy — and genealogy of Key West.”
Her personal life mirrors that same sense of arriving somewhere and staying. She met her husband, Reef Perkins, after deciding to give Key West one more year to deliver either a job or a person she absolutely loved. She and Reef married in 2003. When she’s not organizing an event or scheduling a cleanup, she’s riding her bike, gardening, traveling, scrapbooking, or keeping up with Italian, a language she’s studied since 2010.
Asked what keeps Key West appealing after all these years, DePiero points to the people. “I love that I know the mayor by name, and the chief of police,” she said. “If my car breaks down, or I fall off my bike and break a collarbone — like I did in February — I can always call a friend nearby to help. Key West is a very special place and I love living here, even with the hurricanes.”
