When Ashley Gerry champions a cause, Southwest Florida listens. A co-chair of the 2026 Naples Winter Wine Festival (NWWF), she representsphilanthropic leadership for her generation—one that understands style and substance go hand in hand and that people give when they feel something real.
Her superpower lies in transforming fundraising into experiences guests can’t forget. In 2024, she envisioned a Barbie theme for the Golisano Children’s Museum of Naples’ Night at the Museum fundraiser and reimagined the event tent as the iconic Dreamhouse. This year, she converted the space into a Color Factory, with Warhol-inspired Pop art, and brought in artist Romero Britto as a party guest. In 2023, her psychedelic-era “Imagine All the People” NWWF dinner culminated with children from a local church singing “Imagine” for the group. “It becomes your job basically because you want it to be successful for these organizations,” Ashley says. “But I also have a lot of fun with it.”
That approach has earned her one of Naples’ most coveted volunteer positions. NWWF raises tens of millions each year for the Naples Children Foundation. Co-chairing the event represents a pinnacle of philanthropic leadership, reserved for the most established trustees. Ashley and her husband, Adam—who have attended the festival for nearly 15 years—step in this season, embodying the next wave of patrons resolved to pick up the charge.
Ashley arrived in Southwest Florida 20 years ago from Missouri and dove into the community. She started by volunteering as a pediatric hugger at Golisano Children’s Hospital in Fort Myers. “You get to hold babies all day,” she recalls. “It’s the most incredible ‘job’ you could have.”
Her first event, a fundraiser for the children’s hospital, planned while pregnant with her daughter, launched her trajectory of charitable organizing, with a focus on children’s charities. Since then, she estimates she’s orchestrated about 15 events and helped raise a collective $15 million for organizations like JDRF (now Breakthrough T1D), Youth Haven and the Community School of Naples, where her children attend. After Hurricane Ian, she helped spearhead the Boots on the Ground benefit concert, raising more than $1.5 million for relief efforts. She recently joined Gulfshore Life Woman of the Year Elizabeth Star in leading the Women’s Foundation of Collier County Women Lifting Women Initiative, where they’re helping girls and senior women secure stability and independence.
Ashley instills the same philanthropic spirit in her 11-year-old son and 13-year-old daughter. Currently, they’re gearing up for the holiday toy drive she has the family lead each year. “It’s important for them to start to see the impact they can make,” she says. —Justin Paprocki