Denise Cobb, a former CNN anchor, and her husband, Brian, a media executive, have had some great chefs in their kitchen over the years. Thomas Keller, the owner of the French Laundry in Napa Valley and Per Se in New York, has cooked there three times. Eric Ripert, the chef at Le Bernardin in New York, has been there, too.

This weekend, Brian Boitano, the Olympic gold medal figure skater who is also a television chef, is cooking in their South Florida home — albeit for 32 people whom the Cobbs don’t know all that well.

It’s all for charity, in this case the 16th Naples Winter Wine Festival, a stop on the small but rarefied world of charity wine auctions.

This weekend, 17 dinners, including the one hosted by the Cobbs, will be held in some of the largest and nicest homes in Naples, Florida, a seaside town known for its vast wealth. No dinner will be larger than 40 people, and each one will feature top chefs and vintners.

At the Cobbs’ house, the winemakers Barbara Banke of Vérité and John Lasseter, the chief creative officer of Pixar who also owns Lasseter Family Wineries, were invited. Banke agreed to pour five of her wines that have received top 100-point scores from wine critic Robert Parker.

Unlike many charity auctions, which are fixtures in affluent communities, the price of entry for wine auctions in places like Napa Valley and Naples would constitute a large charitable gift in itself.

In Naples, couples paid $10,000 to be part of the weekend — or $25,000 for two couples who sought to be seated at the same private dinner on Friday. The entry price includes the auction on Saturday and a farewell brunch on Sunday.

At Auction Napa Valley, the oldest charity wine auction in the United States, dating to 1981, the cost ranges from $550 to attend the Napa Valley Barrel Auction, where people bid to buy cases of wine after tasting the wine right out of the barrel, to $4,000 for full access to the auction and events over four days in June.

While these auctions are private affairs, they serve a public need — helping the poorer residents in otherwise wealthy communities. And they’ve been successful enough that the format of drinking, dining and bidding has been copied.

“One of the beautiful things about our auction is it has helped to spur other charity wine auctions around the U.S.,” said Linda Reiff, president and chief executive of Auction Napa Valley. “We’ve had vintners who have helped create them in Naples, Sonoma County, the central coast, even your small elementary school PTA.”

The wine auctions, if they’re to be successful, are complicated affairs.

They start with the auction lots. In Naples, this will be the third time that a Rolls-Royce has been auctioned. Cobb said the first time the organizers struggled to persuade Rolls-Royce to donate a car to raffle off. “They were worried in the beginning that it wouldn’t raise enough money,” she said. “When they saw the amount of money people would bid for things, they changed their mind.”

The second Rolls-Royce, a Phantom Coupe, could have been bought for $500,000, but went for $2 million at auction in 2007. It came with a custom wine cellar in the trunk.

Yet not everyone is into cars or, for that matter, has the desire or ability to pay four times what something is worth, even for charity. So, Cobb said, the quest is for a mix of experiences and rarities to make up the 64 lots of the live auction.

One package is four tickets to the Masters golf tournament, including a private dinner with the golf legend Gary Player and private jet travel to and from Augusta, Georgia. Another is a 14-day trip around Europe on a private jet that holds 15 people. Then, there is the opportunity to watch a Dallas Cowboys football game with the owner, Jerry Jones.

The novelty of the lots is important to bringing people back year after year, festival trustees said. After all, there are only so many people in the country who have the time or money to spend 10 days flying from Napa to London to Paris with the chief executive of Opus One winery. Or if they do, once is probably enough.

However unique the lots are, what someone is willing to pay still depends, as in most auctions, on the mood in the room that day. Reiff said a 12-liter bottle of Screaming Eagle, the largest size made of the cult, limited-production cabernet sauvignon, sold for $500,000 at the Napa auction last year.

But, she said, there have been times when bidders have been so moved by stories they’ve heard that they donate without getting anything but good feelings in return.

“Our top auction lot is Fund-a-Need, which benefits our children’s health and education program,” she said. “You can have someone really moved, and they could raise their paddle and put up $500,000 alone.”

As in Napa, the focus in Naples is on charities to help children and women in the community.

“The one thing that was important was to make a profound difference in the lives of the children in Collier County,” said Valerie Gargiulo, a trustee of the wine festival and vice chairwoman of the grant committee at the Naples Children and Education Foundation, which distributes all the money raised. “The wine auction became our vehicle. We knew that if we had the wine and the great chefs coming, we could attract people.”

Since the first auction in 2001, the Naples Winter Wine Festival has given $135 million to charities in Collier County. Last year, the festival raised $12.3 million.

Gargiulo said the money raised was given to programs focused on mental health, vision and dental care and early child care. The aim is to make up for a lack of tax dollars being spent by the county, she said.

Sandi Moran, another trustee and the vice chairwoman of last year’s festival, said that festival trustees and grant committee members had worked over the last 16 years to prevent overlap in the services offered in the poorer areas of Collier County.

“We asked the charities not to duplicate services so they’d work together,” she said. “We asked them to do more for the children.”

Money raised also pays for periodic studies into what is needed in the area. That was how the foundation arm of the festival came to pay for a mobile dental clinic that treats children at their schools, and was also to start a program to give eyeglasses to any child who needed them.

As to replicating the success of these auctions, Reiff of Napa Valley suggested a cautious approach. Putting on a good charity wine auction is going to take much more time than people expect, she said.

“My advice would be to start small and stay focused,” she said. “Don’t try to be all things to all people, have clear and understandable causes that you’re raising money for and have a great committee.”

As the Naples festival was about to get underway, Moran did not stress the work that went into it — every trustee commits to hosting and paying for the dinner — but the uses of the money raised.

“People sometimes don’t understand that the festival is not just a big party,” she said. “We have a reason for it. We have the Naples Children and Education Foundation and the Naples Winter Wine Festival is how we raise money each year. There is a reason for this great party.”

The hope is that many well-heeled people will drink to that.