Anderson Andrews vitner dinner 2016
Anderson/Andrews 2016

Inside Naples Winter Wine Festival's Legendary Vintner Dinners

As NWWF celebrates 25 years of fundraising for Collier kids, we pull back the curtain on the nonprofit's lavishly planned Vintner Dinners, which kick off the festivities, priming guests for radical giving.

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What does it take to raise more than $30 million in a weekend? For Naples Winter Wine Festival, it starts with 17 regal, intimate dinners. 

In the beginning, 25 Naples seasons ago, a crew of well-connected snowbirds—oenophiles with vintners in their ranks—set out to bridge the gap in Collier County’s spending for children’s services. Inspired by Auction Napa Valley and armed with Naples’ trademark hospitality, the crew birthed the Naples Winter Wine Festival (NWWF). The result? A cool $300 million and counting, all directed to Naples Children & Education Foundation’s (NCEF) robust network of programs for Collier kids. At the core of the festival’s winning recipe lie the Friday night Vintner Dinners—small, beyond-bespoke suppers designed to ignite generosity. “The excitement people show up with on Saturday morning is built, in part, on the experience they had the night before,” says NCEF founding trustee Jeff Gargiulo. Shrouded in mystery, the lavishly planned gatherings are pure Naples legend. As a new philanthropic season and NWWF’s silver jubilee approach, we’re pulling back the curtain on the town’s most successful dinner party, tracing 25 years of haute wining and dining with a purpose. 

The Ambience         

Elegance with a heavy dose of whimsy  

Vintner Dinners are mostly hosted in the palatial homes of NCEF trustees, the nonprofit’s lead patrons—and that’s by design. “We want people to feel that though they may only be here once a year, they’re part of the community,” says Kelley Bailey, co-owner of Knights Bridge Winery and an NCEF trustee. When she set eyes on her new Port Royal home, the first thing that came to mind was NWWF. “I’m not thinking about an extra bedroom or anything—just, ‘Oh, we can do such a nice dinner here,’” she laughs.   

When not using their grandiose residences—from gilded Gulfside villas to Pelican Bay penthouses overlooking mangroves to Pine Ridge Estates’ abodes surrounded by Jim Dine and Bob Rauschenberg works—hosts recruit tony venues, like Naples Botanical Garden or a private hangar, where bare walls lend themselves to immersive art experiences. 

Fog machines, elaborate florals, illuminated poolscapes and custom decor underscore the whimsical nights, which often evolve from refined elegance to joyous celebration with spontaneous dancing. Add novel entertainment (contortionists, mentalists, Tony-winning singers), and you start to see the magic. 

The Food & Wine         

Singular wines and bites, artfully plated

There aren’t many occasions when culinary titans like Wolfgang Puck, Emeril Lagasse and Olivier Krug assemble in one place to collaborate on mind-blowing meals for a select few. “It’s just something you can’t buy,” says founding trustee Denise Cobb. Each dinner gets a chef and one or two vintners, with committees working year-round to secure a star-studded lineup. 

Festival founders set the bar sky-high from year one. Winery-owning trustees tapped their connections to bring in cult labels Staglin, Grace, Screaming Eagle and Harlan. “We laid out the promise that, if you come to our event, we’re going to treat you like a VIP,” Jeff, who also co-owns Gargiulo Vineyards, says. 

The royal treatment, coupled with NCEF’s measurable impact, keeps the heavyweights returning. Leading up to the big night, chefs and vintners collaborate on designing artful menus. “If you’re going to raise $30 million, you expect the best of the best,” says Silver Oak Cellars’ owner and longtime NWWF participant David Duncan, who plans to auction a 25-year vertical of Silver Oak magnums for the anniversary.  

The team pairs chefs and vintners who will bring out the best in each other’s creations. Every course is a masterpiece, featuring exotic ingredients and remixes of chefs’ signature haute dishes—imagine an ostrich egg scramble with oysters and caviar or Tom Colicchio’s rich, meltingly tender braised short ribs. Guests sip on large-format library wines and coveted vintages like OVID’s Hexameter or Harlan Estate’s The Maiden, poured by master sommeliers. Between courses, the makers share tasting notes and intimate stories, from ingredient sourcing to culinary philosophies. For gourmands, it’s pure heaven. 

The People           

Star talent and style to spare

At the season’s most prestigious social event, the guest list is as curated as the wine selection. Industry titans rub shoulders with Michelin-starred chefs, revered winemakers and master sommeliers, the occasional celebrity, and NCEF trustees—a venerable list of Naples’ who’s who. The mix makes for a mosaic of influence and passion, capped at a cozy 40 guests per dinner.

Behind the scenes, there’s a small army of kitchen staff, party planners, floral and lighting designers, NCEF staffers, drivers and volunteers ensuring it all goes smoothly. The trustees—who host and cover food and decor expenses to keep all festival fundraising directed toward the kids—play a crucial role in orchestrating these social symphonies. They research their guests and craft seating charts like matchmakers, ensuring a blend of personalities promising engaging conversation and potential alliances (patrons often split blockbuster travel packages at the Saturday auction, with partnerships and strategies cemented at the dinners). 

“The dinners serve a key role in so many ways,” Jeff says. The intimate settings allow hosts to expand on NCEF’s mission and stoke interest in auction lots. Kelley recalls the awed faces of her dinner’s winemaker, Derek Baljeu, and chef, Philip Tessier, when the Knights Bridge lot went for $800,000 last year. “[The next day], when they come under the tent, see the enthusiasm and realize what they’ve been a part of—it’s so gratifying,” Kelley.  

Exclusivity is a big part of the allure. Those members-only bottles of Screaming Eagle and Harlan you can’t get in a store or even at the winery? At a Vintner Dinner, you won’t only meet the winemaker—you’ll also get on the list, Denise says. 

From the moment they’re whisked from their homes in black cars to the final nightcap, every attendee is made to feel like the guest of honor. David says the dinners emphasize the best part of the festival: “Getting to know the folks there is the joy.”