The Naples Winter Wine Festival has unveiled the first batch of live auction lots for its 2027 event, a lineup that includes a limited-edition Bentley, a private château stay in Burgundy and a four-day trip to the Cannes Film Festival. The festival returns to The Ritz-Carlton Naples, Tiburón on January 29-31, 2027, with proceeds again benefiting the Naples Children Foundation and its work supporting vulnerable children in Collier County.
Organizers announced the lots Tuesday, according to WINK News, giving an early look at what bidders can expect when the live auction convenes on Saturday, January 30. The festival carries the theme Hope Sings: A Brighter Tomorrow Takes the Stage, according to Life In Naples Magazine, and auction offerings this year span luxury travel, wine experiences and the aforementioned Bentley.
What's on the Block So Far
Among the highlighted lots are seven nights in a private villa in Punta Cana, Dominican Republic, and a 2027 Bentley Supersports with Mulliner configuration. Also featured are four nights with private use of Château de la Crée in Burgundy, France, and a nine-night trip through Thailand and Cambodia that includes stops in Bangkok, Siem Reap and Chiang Mai, along with tours, culinary experiences and a private dinner within the temples of Angkor.
Other featured packages include five nights in Argentina with Terrazas de los Andes and five days in Vail, Colorado with Silver Oak at the Duncan family's private residence. A Cannes Film Festival package covering four days in May 2027 includes a red carpet premiere, Chopard party access and a $25,000 credit toward a high jewelry purchase. The festival also announced a separate lot dubbed Million Dollar Meal…All For the Kids!, which includes an exclusive dinner at Mika in Coral Gables on November 16, 2027.
Ashley Gerry, a member of the festival's auction lot committee, said the first collection of auction lots combines exceptional experiences and sought-after wines with donor generosity, benefiting vulnerable children in Collier County. Valerie Boyd, the 2027 festival's co-chair and a fellow auction lot committee member, added that the live auction offers rare experiences through luxury brand and donor partnerships, inspiring generosity among attendees.
How to Get In the Door
How to Get In the Door Tickets are sold as packages covering the entire festival, and individual events cannot be purchased separately, except for The Vintage Cellar, which is a separate ticketed event, per the Naples Winter Wine Festival's own ticket page. Packages start at $17,500 per couple for a Double Magnum package, while a Jeroboam package runs $40,000 for two couples, the organization's site notes. The three-day festival kicks off Friday morning with the annual Meet the Kids Day, followed that evening by 16 intimate vintner dinners hosted by Naples Children Foundation trustees, Life In Naples Magazine reported.
Where the Money Has Gone
The 2026 festival raised more than $30 million at its live auction, part of a broader total that organizers say has topped $366 million raised since the event's start. Life In Naples Magazine has reported that figure dates to the festival's inaugural event in 2001, while Gulfshore Business has put the same $366 million total against a 2000 start date and said the festival has supported more than 385,000 children in Collier County — a number that diverges from the foundation's own claim, relayed by Life In Naples Magazine, of 420,000 children served through its annual grants and strategic initiatives. The Naples Children Foundation says it has impacted nearly 90 nonprofits in the local community, and according to its own impact reports, it has invested in programs intended to create lasting change for the county's most vulnerable children.
Recent auctions give a sense of scale. The 2025 festival raised more than $34 million, a record at the time and about $1 million more than the prior year, according to Wine Spectator, with 52 lots on the block and a top sale of $1.7 million for a 2025 Bentley Continental GT Speed Convertible. A private concert and dinner with Scotty McCreery sold for $1 million that year, and an eight-night Croatian Coast yachting voyage for four couples went for $850,000, per the Naples Daily News. The foundation's online auction has also become a steady fundraising arm, raising nearly $6 million since it began in 2015, according to WINK News, with its 12th annual edition alone bringing in over $1 million across more than 100 lots, led by a $31,000 Bahamas escape package.
