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From the Editor

Elegance. glamour. heart. and, yes, Deep Pockets. We’re talking, of course, about the Naples Winter Wine Festival, an annual rite that in many ways defines our town and certainly brings us renown the world over.

In this issue, we offer a special section (see p. 57) to take you inside the 11th running of this extraordinary event. You’ll meet the top chefs and vintners coming to town, learn of the most exclusive wines to be sipped and auctioned, hear trustee memories of unforgettable moments from the past and—most poignantly—get acquainted with some of the kids whose lives benefit from the $82.5 million raised over the first 10 years.

But I wanted to know more. Who’s running this year’s show? And what exactly do they do to make it so successful? Enter co-chairs Bruce and Cynthia Sherman. Bruce (very smart, very savvy) and Cynthia (charming, deeply intelligent) give full credit to the team effort from their fellow trustees, the festival employees and the army of volunteers.

Yet, what is it like for a powerful financial guru like Bruce and a successful corporate lawyer like Cynthia
to have to watch the pennies and go gently into the business of friendly persuasion?

Says Bruce, sheepishly, “I learned to beg.”

Says Cynthia, knowingly, “It’s been like staging a couple of weddings at once.”

They divided their chores to play to their individual strengths. Bruce, strategic, determined, with a keen eye for reading people and making deals, took on the building of the fabulous lots for auction. Cynthia, with her great taste, people skills and command of detail, assumed responsibility for the look and feel of the event itself.


The Lots Challenge

Push the right button and Bruce is off on a recitation of the travels, calls, meetings and trials on the way to landing some pretty amazing offerings. He allows that this beseeching was “a huge role change” for him. “Some people say no, especially in this economy,” he notes. “And there’s no manual in how to do this.” But the yeses prevailed and here’s a sample that, as a native New Yorker, I just have to share. This lot is called “The Ultimate New York Experience” and—wow!—this is some of what you’d get in this package for four people: six nights in a swanky Fifth Avenue apartment overlooking Central Park; two chauffeured Lexus vehicles throughout the stay; wining and dining in such restaurants as Per Se, Babbo’s, Gramercy Tavern, Aureole and The Modern; tickets to the Tony-winning Broadway show Memphis; private magic lessons with David Blaine; a dinner with (Judge) Judy and Jerry Sheindlin at their Greenwich, Conn., home; tickets to a Yankee game and a Madison Square Garden event; dinner with Regis Philbin and his producer Michael Gelman after attending a taping of LIVE! with Regis & Kelly; a special fitness class with Kelly Ripa at her gym; a visit to the set of Gossip Girl; and a behind-the-scenes tour of the world-famous Christie’s Auction.


The Look and Feel

Meanwhile, Cynthia was getting creative to invest an event with elegance and fun and still, she says, “keep to the budget.” The pop art theme emerged, inspired by Andy Warhol, and Cynthia engaged the talented Sherri Morrison as the graphic designer. See our special section cover for vivid evidence of her striking artistry. It’s the work on the details that will give texture to festival events—the tablecloths, napkins, chair backs, centerpieces—and you can look for bright pinks, oranges, yellows and purples to dazzle in just the right way.


Finally …

The planning and arranging are done. It’s been a year in the lives of the Shermans. “I couldn’t have done this if I were still working,” says Bruce. The Shermans feel good about what their team has put together. “But,” says Bruce, “if the balloons fall down at the auction, if the snacks aren’t good enough, if the auctioneers have a bad day, if it’s too hot in the tent … they’ll be looking at the co-chairs.”

Fear not. When you have the gold standard in the art of “begging” and “wedding planning,” you can count on a world-class Naples Winter Wine Festival. As ever.

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