David and Diane Carpenter have enjoyed a long history of vacationing in Naples. From their first visit in 1994 they admit, “We were hooked.” Over the years, stays at various beachside resorts with daughters Kimberley and Chelsea in tow solidified their affection for the area. In 2003, they purchased a villa in the Park Shore area.
During walks along picturesque Gulf Shore Boulevard, the couple would gaze up at the stately high-rise condominium buildings. They grew particularly fond of Le Ciel Park Tower and would wistfully quip, “Wouldn’t it be great to live there one day?”
To their surprise and delight, it happened in 2019. One of the penthouses became available for sale. In its original condition, the condo—with wall-to-wall carpeting and walls troweled thick with aging paint—showed its age. David and Diane instead saw stunning views and immense possibility. They hired PBS Contractors for the renovation work and commissioned Denise Fogarty’s interior design expertise.
Diane, who has always enjoyed creative work, also contributed her talents, choosing a minimalist vibe for the 3,600-square-foot space. White—present on the walls, the ceiling, the floor, and much of the furniture—became the dominant color. “I had to fight for the blue sofa in the great room,” remarks David.
The result is a peaceful space 20 stories above the ocean where, when at work on their laptops, the couple are only distracted by kiteboarders cavorting in the sky, dolphins frolicking in the saltwater, and herds of manatees huddling near the shore. “Somedays we don’t want to leave,” they say.
The couple credit their fortune to immense hard work and a bit of luck. David, a lawyer who specializes in mergers and acquisitions, works for a large Chicago-based law firm. At present, he travels between Naples and New York City. Diane was a stay-at-home mom for 20 years. Their daughters were born in London, England, but raised in the United States.
In 2004, a sip of Cabernet Sauvignon forever changed the course of Diane’s life. “It was absolutely phenomenal,” she remembers. She was with a group of wine aficionados at Zoe’s, a restaurant on Fifth Avenue South (no longer extant), when she took the transformative taste. A friendship with the makers of that fabulous Cab, Paul and Christina Hobbs, followed, and Diane began learning everything she could about wine.
In 2014 she and David bought 4 acres of property in Sonoma County, California, and commissioned crews to help convert a 1.5-acre horse paddock into the Ross Knoll Vineyard. “I left the [wine] books to live my passion,” she says. In 2017, Diane and team planted 3,000 Pinot Noir vines. The first harvest, reaped in 2019, included a rosé—Cuvée Kimmie—named after their eldest daughter and served at her wedding celebration that year.
During Diane’s years of vineyard ownership, she experienced multiple hardships: fires, frost, and even COVID. Eventually, the couple decided to sell the California property, maintaining an evergreen contract allowing them to source fruit from the land for their wines. The goal now is to produce 300 cases a year, mostly for friends and family.
Following the pandemic, when working remotely became more popular and possible, the couple decided to cut down on their travel. The self-described nomads sought a more permanent sense of place in their lives. With a capable team of winemakers in place, barrel samples can easily be sent to Florida for Diane to review, no longer necessitating travel to California six times a year. The Carpenters have whittled down home ownership to residences in Chicago’s Gold Coast and Naples—where following the pandemic, they welcomed their daughter, her husband, and their grandchildren as neighbors.
Today, much of their conversation and conviviality takes place over wine. Diane happily shares her knowledge while treating fine-wine palates in a blissful setting high above the Gulf of Mexico. “Everybody loves her product,” says David. Diane continues to host blending events—often out of town. She also contributes her viticulture knowledge as a partner in a documentary production company, Forgotten Man Films, which just launched a streaming network called Somm TV, a forum designed to provide information and entertainment related to food and wine.
While the Carpenters continue to work on making their world a smaller place, Naples remains a constant in their lives. “We have found a really good spot for us,” they declare.
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