Ashley and Adam Gerry Share Their Gift of Giving

One of Ashley Gerry’s favorite childhood memories is bonding with her family over a holiday movie. “Every year, we would watch A Christmas Story by the fire,” she says. Adam Gerry’s fondest recollections from his youth were Christmas Eve dinners at his grandmother’s home. Naturally, at the heart of the couple’s own yuletide celebrations are their loved ones—especially daughters Alexandra, 23, Isabella and Cassandra, both 20 (born two months apart and adopted from Guatemala), Aniston, 13, and son Parker, 11. “My family is my world,” Adam says.

The Gerrys typically get a head start on the merriment in mid-October, when the lights adorning the exterior of their Tuscan-style Port Royal residence are installed. The custom display by Light Up Naples illuminates the property through early February, with the colors changing according to each month’s holiday theme.

Each year, they recruit Naples artist Clayton Brown, owner of Clayton Creations, to decorate the interior of the home for the holidays, as he has since 2013. “Ashley and Adam are always excited about Christmas, and I’ve seen the kids grow up, so theirs is one of the homes I most enjoy decorating,” he says. “It’s a tradition I look forward to every year.” The home’s Italian ambience serves as a springboard for the holiday decor’s rich palette. (Think: lush textures and saturated colors of gold, bronze, copper, topaz, and olive green, with pops of red, plum, and turquoise.)

A highlight of the ornamentation is the stairwell balustrade, which is scalloped with pine garland, entwined with lights, and embellished with large bows of chocolate brown velvet and shimmering metallics. Clusters of colorful glass orbs and sugared fruit are nestled into the greenery, while gold stockings embroidered with the family’s names dot the arrangement.

In the living room, a stunning 12.5-foot tree glints with warm white lights and wide, gold velvet and metallic ribbon encrusted with crystals and pearls. The tree is festooned with a variety of ornaments, along with flowers, birds, butterflies, berries, and peacock feathers. Whimsical elves and fairies peek through the foliage.   

The formal dining room, where the Gerrys will host Christmas Eve dinner for family and close friends, features an impressive array of nutcrackers, from a few inches high to a few feet tall. An ever-increasing collection of Santas perch artfully on tabletops, sideboards, and in alcoves and trees throughout the home. “Our storage keeps growing,” Ashley says with a laugh.

The family will celebrate Christmas morning in the wood-paneled sports bar, which houses Adam’s enviable collection of memorabilia. The warm space is decorated with a 10- to 12-foot live tree trimmed with treasured ornaments—some made by the children, others collected during the family’s extensive travels, and several saved from Ashley’s childhood. “These are things you can’t replace,” she notes. Later that day, the family will gather for dinner to fete Adam’s dad, Cablevision Industries founder Alan Gerry, for his ninety-seventh birthday.

The Gerrys will continue their annual tradition of chartering a trolley and transporting up to 30 family and friends clad in ugly Christmas sweaters to view the holiday lights in Victoria Park. Another special occasion is on tap for New Year’s Eve, when Ashley and Adam celebrate their fifteenth wedding anniversary.

Seasons of Generosity

For the Gerrys, the giving season is not just at Christmastime; it’s throughout the year. Their steadfast commitment to philanthropy will shift into high gear next month when they co-chair the twenty-sixth annual Naples Winter Wine Festival, January 30-February 1. The prestigious charity fundraiser benefits Naples Children Foundation (NCF), for which the couple serve as trustees and Ashley sits on the board.

NCF is one of the many causes to which the Gerrys devote their time, talent, and treasure. Adam dove into the local charity pool shortly after relocating to Naples more than two decades ago when he discovered an invitation to a fundraiser for Juvenile Diabetes Research Foundation (now known as Breakthrough T1D) in the mailbox on the property where he was building a home. Not knowing many people in town, he decided to attend and later learned that some of his children’s classmates were coping with the ailment. “It turned from a party for a cause to something more personal,” he says.

In addition to his ongoing patronage of Breakthrough T1D, Adam supports Community School of Naples and Naples Comprehensive Health (NCH). He sits on the boards of The Frederick Gunn School in Washington, Connecticut; Gerry Foundation in his hometown of Liberty, New York; and Bethel Woods Center for the Arts in Bethel, New York (the historic site of the 1969 Woodstock Music Festival). “I feel blessed for the wonderful opportunities I’ve had in my life, and when you have these opportunities, you want to give back. You have to give back,” he says.

Ashley’s philanthropic journey also began soon after moving to Naples in 2007, when she volunteered as a pediatric hugger at Golisano Children’s Hospital. “It was the best job I’ve ever had,” the Missouri native says. Her dedication to that organization endures, and she also serves on the board of Golisano Children’s Museum of Naples. In addition to supporting Breakthrough T1D and Community School of Naples, she is a benefactor of the Women’s Foundation of Collier County and Youth Haven. She has chaired myriad fundraising events for every organization fortunate enough to have her patronage.

In the wake of Hurricane Ian in 2022, Ashley helped spearhead Boots on the Sand—a benefit concert at Hertz Arena featuring Lynyrd Skynyrd, Ted Nugent, Gavin DeGraw, Tracy Lawrence, Ira Dean, and Jim Breuer—raising more than $1.5 million for local citizens affected by the devastation. “It truly was a wild and rewarding experience to be a part of,” she says.

The Gerrys’ friend, Marissa Hartington, founder of Marissa Collections in Naples, sees the couple as role models for making a difference. “They have an absolute commitment to the community and to the causes that are important to this town,” she says. “They’re an inspiration for others to become involved.”

For those who aspire to make a difference in the community, Adam offers this advice: “You can’t do everything. You can’t solve all the world’s problems, so you have to find what means the most to you and where you can have the greatest impact.”

Adam’s education—including a bachelor’s degree and master’s degree in business administration from Rollins College in Winter Park, Florida, and a juris doctor law degree from Syracuse University—serves him well as chairman and CEO for Granite Associates, the Gerry family’s private investment firm. The avid sports enthusiast—an investor in the Tampa Bay Lightning pro hockey team and D.C. United pro soccer team—delights in taking the family to Yankees and Mets baseball games when they visit New York. He also sips and socializes with fellow members of La Confrérie des Chevaliers du Tastevin, a French Burgundy wine society.

Ashley honed her keen sense of style at the University of Missouri in Columbia, where she graduated with a degree in fashion marketing. “I toy with Marissa [Hartington] that I’m going to come work for her when I have the time,” she jokes. Says Hartington, “I tease her back and tell her, ‘I wish you would.’ She has amazing taste.”

The fashion-forward residents of Naples likely won’t have a chance to consult with Ashley at Hartington’s boutique any time soon, however. She’ll likely be too busy with her year-round focus on family, friends, and philanthropy.

Story Credits:

Shot on location at the residence of Adam and Ashley Gerry, Naples

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