Naples Winter Wine Festival raises more than $30M at live auction

5:49 p.m.

Lot 51: Fund a Need: The Picture of Health 

Unofficial total raised for lot: More than $7 million 

Unofficial total raised for auction: About $30.8 million 

Make a lasting difference in the lives of children by funding the future of pediatric health in Collier County. This year’s Fund a Need focuses on health care, addressing critical gaps in mental health, oral health, vision and primary care services to ensure every child receives the support they deserve. Every bid directly advances access to life-changing treatment, early intervention and long-term wellness for vulnerable children and families. Together, we honor the impact of past generosity while building a healthier future for the next generation. Move forward with us. Make a difference with us. Embrace the challenge with us. Remember, it’s all for the kids. 

5:28 p.m.

Lot 50: Paying It Forward 

Winning bid: $400,000 

Secure a front-row seat to the 2027 Naples Winter Wine Festival while taking home exceptional luxury. Two couples will enjoy a jeroboam package including 3 nights at The Ritz-Carlton Naples, Tiburón, access to all festival events, premium auction seating and car service to their chosen vintner dinner. The tangible centerpiece is a 2026 Mercedes Ultimate Toys Luxury J Lounge Limo Sprinter van, finished in black with sand leather interior and custom Naples Winter Wine Festival touches. Completing the experience is a $30,000 credit toward fine jewelry at International Diamond Center. Back home, the vehicle and memories become enduring symbols of generosity, celebration and commitment to children’s futures. 

5:24 p.m.

Lot 49: Trustee Treasure Trove 

Winning bid: $380,000  

Acquire a world-class wine collection curated to define the ultimate cellar. This extraordinary lot features iconic producers and elite formats, from imperials and double magnums to magnums and standard bottles. Highlights include Château Palmer, Domaine du Comte Liger-Belair, Château Latour, Château Mouton Rothschild, Château Trotanoy, Colgin, Harlan, Hundred Acre, Petrus, Vérité, Pulido Walker, Pingus and Shafer Hillside Select. Complementing the collection is a custom high-top table by Method & Concept and Thomas Riley Artisans’ Guild, paired with four drink disks and six handblown glasses designed for refined tasting. Back home, this remarkable ensemble becomes a centerpiece of hospitality, celebration and legacy, offering an unmatched opportunity to steward some of the world’s most coveted wines. 

5:20 p.m.

Lot 48: Isle Be Back: Adventures in the Galápagos 

Winning bid: $800,000  

Explore one of the planet’s most extraordinary ecosystems with a private yacht expedition to the Galápagos Islands. Four couples will enjoy 9 nights beginning with 2 nights in Quito at five-star Casa Gangotena, featuring guided touring of Old Town and the equator, plus a cultural evening with traditional dance and Ecuadorian cuisine. Then sail for 7 nights aboard the 124-foot Galapagos Explorer, visiting Santa Cruz, Española, Floreana, Bartolomé, Genovesa and Daphne Major with expert-guided wildlife excursions, snorkeling, kayaking and gourmet dining. The vessel offers luxury suites, a Jacuzzi and attentive service from an 11-member crew and two bilingual naturalists. Back home, the adventure lives on through unforgettable encounters with nature, all meals and logistics seamlessly included. 

5:12 p.m.

Lot 47: Fast Track to the French Riviera 

Winning bid: $450,000 

Live the glamour of Formula 1 aboard a floating five-star sanctuary. One couple will enjoy 5 nights from June 3–8, 2026, aboard The Ritz-Carlton Yacht Collection’s Evrima, featuring a terrace suite with two nights in Saint-Tropez and two nights in Monte Carlo. The centerpiece includes two VIP tickets to the Monaco Grand Prix with exclusive viewing access, complemented by gourmet dining, select beverages and special onboard experiences. Additional highlights range from celebrity-hosted events to fashion showcases and curated shore excursions. Back home, the experience resonates as one of motorsport’s most iconic weekends. All-inclusive yacht fare and roundtrip business-class airfare to Nice, France, are included, ensuring seamless luxury from start to finish. 

5:07 p.m.

Lot 46: The Grand Tour of Dolce & Gabbana Alta Moda 

Winning bid: $380,000  

Enter the world of haute couture at its most exclusive with a coveted invitation to Dolce & Gabbana Alta Moda. One couple will enjoy 6 nights in Italy from July 12–17, 2026, staying in luxury accommodations at a yet-to-be-revealed destination, paired with five days of elite fashion experiences. Highlights include a welcome celebration, high jewelry presentation and dinner, two runway shows followed by seated dinners and a final gala party. Back home, the experience continues with a $15,000 shopping credit toward Dolce & Gabbana clothing at Saks Fifth Avenue Naples and a limited-edition Dolce Box “L’Amore è Bellezza” handbag. Roundtrip business-class airfare to Italy is included, delivering the ultimate expression of Italian style and craftsmanship. 

5:02 p.m.

Lot 45: The Summit of Taste, Health and Wellness 

Winning bid: $170,000  

Rejuvenate body and spirit on a European wellness journey anchored by Michelin-starred cuisine and elite spa science. Two couples will enjoy 9 nights beginning with 2 nights in Kaysersberg, France, at Relais & Châteaux Le Chambard, including dinner at 2-Michelin-starred La Table d’Olivier Nasti and a Trimbach family-hosted vineyard tour, tasting and lunch. Continue for 7 nights at Chenot Palace Weggis in Switzerland, where each guest receives a personalized wellness program featuring advanced detox, recovery, prevention or sleep therapies, plus three healthy meals daily. Back home, each couple receives an extremely rare 3-liter bottle of 2016 Trimbach Riesling Clos Sainte Hune, a fitting finale to a transformative experience. 

4:55 p.m.

Lot 44: Vanquish Velocity: Waves and Wheels 

Winning bid: $1.1 million 

Own automotive artistry paired with a high-octane Miami driving experience. The winning bidder receives a one-of-a-kind 2026 Aston Martin Vanquish Volante convertible finished in Iridescent Sapphire with Glacier White leather, Gloss Black carbon fiber accents and Pale Blue contrast stitching. The thrill continues with a 1-night VIP Miami escape featuring an ocean bungalow stay at the five-star Four Seasons Hotel at The Surf Club, followed by a four-hour private driving session at The Concours Club. Culinary highlights include a multicourse wine-paired meal at Verge by Chef Brad Kilgore and a tasting menu dinner at Lido Restaurant. Back home, the Vanquish becomes a rolling statement of luxury, engineering and exclusivity. 

4:49 p.m.

Lot 43: Crown Jewels to Coastlines: A Lavish European Escape by Land and Sea 

Winning bid: $420,000 

Embark on a sweeping European journey that blends royal intrigue, diamond heritage and Mediterranean cruising. Two couples will enjoy 14 nights beginning with 3 nights in London at The Dorchester in deluxe junior suites, including a full-day “Diamonds in the Rough” experience hosted by auctioneer Humphrey Butler, featuring private visits to the Tower of London, Hatton Garden and Sir John Soane’s Museum, plus a gallery lunch. Then sail for 11 nights aboard The Ritz-Carlton Yacht Collection’s Evrima in The Loft Suites, visiting Cowes, Bordeaux, Porto, Lisbon, Cartagena and Ibiza with all-inclusive dining and personalized service. Back home, memories span continents. Roundtrip business-class airfare to London and returning from Barcelona is included. 

4:45 p.m.

Lot 42: The Best of Vega Sicilia and Spain’s Basque Country 

Winning bid: $280,000  

Experience Spain’s most coveted wines and cuisine in a journey few collectors will ever replicate. Two couples will enjoy 5 nights split between Valbuena de Duero and Bilbao. Begin with 3 nights near Vega Sicilia, including a private VIP estate tour, tasting and multicourse lunch, followed by a wine-paired lunch at Michelin-starred Asador Etxebarri and dinner at 3-Michelin-starred El Celler de Can Roca. Continue for 2 nights in Bilbao with visits to Torre Loizaga’s Rolls-Royce collection and a private tasting at Marqués de Riscal in Rioja. Back home, winners receive a priceless vertical of Vega Sicilia Único in magnum format, spanning vintages from 1970 to 2010. Roundtrip business-class airfare to Spain is included. 

4:40 p.m.

Lot 41: Game, Set, Style 

Winning bid: $350,000 

Serve up courtside prestige and Manhattan luxury at the pinnacle of professional tennis. Two couples will enjoy a bespoke 3-day U.S. Open experience in New York City in September 2026, including 2 nights in superior suites at The Carlyle, A Rosewood Hotel. The centerpiece is four courtside seats to the men’s or women’s singles finals, delivering unmatched proximity to championship play. Signature inclusions include an elegant dinner at Ralph Lauren’s Polo Bar, personalized itinerary planning by the Ralph Lauren team and two $5,000 shopping credits at the Madison Avenue flagship store. Back home, style and memories extend long after match point. Roundtrip first-class airfare to New York is included, ensuring a seamless Grand Slam escape. 

4:36 p.m.

Lot 40: Million Dollar Night of Country with Thomas Rhett 

Winning bid: $1.375 million 

Experience an unforgettable night of country music in an intimate aviation setting designed exclusively for Naples Winter Wine Festival patrons. Fifty-five couples will gather at Naples Jet Center in November 2026 for a private performance by country superstar Thomas Rhett, whose career includes 24 No. 1 singles, 16 billion streams and multiple ACM and CMA awards. The evening unfolds inside a 30,000-square-foot hangar transformed into a luxury concert venue, featuring concierge-level service, casual gourmet cuisine and premium beverages. Guests will enjoy front-row proximity to one of Nashville’s brightest stars, surrounded by sleek aircraft and festival friends. Back home, the memory of this extraordinary musical night endures, representing the perfect blend of entertainment, philanthropy and once-in-a-lifetime access. 

4:34 p.m.

Lot 39: Stars, Cinema & Chopard Splendor 

Winning bid: $400,000 

Total raised so far: $17.69 million 

Step onto the world’s most glamorous red carpet for a cinematic experience reserved for the elite. One couple will enjoy 3 nights in Cannes during the 2026 Cannes Film Festival, staying at the iconic five-star Hôtel Martinez. Highlights include walking the red carpet for a major film premiere, reserved seating at the legendary Chopard Party and a hosted dinner at a five-star restaurant. Guests will enjoy access to the exclusive Chopard Rooftop for hair and makeup, gourmet dining and champagne, plus a private viewing of Chopard’s 2026 High Jewelry Red Carpet Collection. Back home, the glamour continues with a $25,000 credit toward a high jewelry purchase. Roundtrip business-class airfare to France is included, delivering a truly star-studded escape.

4:28 p.m.

Lot 38: The Beauty and Majesty of Lake Como with Black Book Villas 

Winning bid: $1.1 million 

Total raised so far: $17.29 million 

Live the Italian dream in a world-class villa on one of Europe’s most glamorous lakes. Four couples will enjoy 7 nights at Villa Polli on Lake Como, a lavish estate featuring seven ensuite bedrooms, a heated pool, Jacuzzi, sauna, hammam, fitness room, cinema and game rooms, lush gardens and full daily service from a private chef and butler. A 24-hour concierge curates unforgettable experiences, including a private three-hour Giuditta boat tour and a multi-course dinner at Hotel Passalacqua, named Best Hotel in the World. Leisure time invites lakeside lounging, village strolls and sunset aperitivi. Back home, the memories of shimmering waters, alpine views and Italian indulgence linger long after departure, defining a once-in-a-lifetime escape. 

4:20 p.m.

Lot 37: From Summit to Shoreline, The Montage Way 

Winning bid: $260,000 

Total raised so far: $16.19 million 

Experience the ultimate dual-destination luxury escape with Montage, blending alpine adventure and coastal serenity. Three couples will enjoy 8 nights split between 4 nights in Deer Valley, Utah, and 4 nights in Palmetto Bluff, South Carolina. In Deer Valley, stay in expansive suites at Montage Deer Valley with daily breakfast, a 60-minute spa massage per person and seasonal activities ranging from sleigh rides and dogsled adventures to fly-fishing and luxury boating, depending on travel timing. In Palmetto Bluff, enjoy a 3-bedroom residence at Montage Palmetto Bluff, daily breakfast, golf cart access, spa treatments and a multi-course wine-paired dinner hosted by a Bryant Estate representative. Back home, memories linger from two iconic resorts. Roundtrip private air from Naples to Heber City, Utah, aboard a Citation Latitude is included. 

4:15 p.m.

Lot 36: Cabernet and Carats 

Winning bid: $400,000 

Total raised so far: $15.93 million 

Pair legendary Napa cabernet with rare high jewelry for an ultra-exclusive California and Las Vegas escape. Two couples will enjoy 5 nights beginning with 3 nights in Napa at Harvest Inn, featuring private tastings and a multicourse wine-paired dinner at Naoko Dalla Valle’s home, plus dinner at 3-Michelin-starred The French Laundry. Continue for 2 nights in Las Vegas in Fleur de Lis Suites at the five-star Fontainebleau, including full butler service, a private Graff high jewelry viewing with a $20,000 credit per couple, VIP entertainment, spa treatments and a Grand Canyon helicopter tour. Back home, each couple receives verticals of Dalla Valle’s Maya and MDV, plus bottles of Delaire Graff Estate Cabernet. Roundtrip business-class airfare and one-way private air from Napa to Las Vegas are included. 

4:11 p.m.

Lot 35: Eight Knights on a Grand Greek Odyssey 

Winning bid: $850,000 

Total raised so far: $15.53 million 

Set sail on a private Greek island odyssey that blends ancient culture, crystalline seas and floating luxury. Four couples will enjoy an 8-night journey beginning with 1 night at a luxury hotel in Corfu or Zakynthos, followed by 7 nights aboard the 164-foot ORIY private charter yacht. The curated itinerary includes stops in Corfu, Parga, Antipaxos, Lefkada, Kastos, Ithaki, Kefalonia and Zakynthos, with bespoke cultural, culinary and wine experiences ashore. Onboard, savor gourmet meals prepared by a private chef, attentive service and sweeping Mediterranean views. Back home, winners receive premium Knights Bridge wines in magnums and one methuselah. One-way private air on a Citation Longitude and one-way business-class airfare are included, based on sailing dates. 

4:06 p.m.

Lot 34: Balmain Unbound: Paris Edition 

Winning bid: $350,000 

Total raised so far: $14.68 million 

Enter the rarefied world of haute couture with unparalleled access to Paris Fashion Week. Two couples will enjoy 5 bespoke nights in Paris in fall 2026 or spring 2027, staying in luxury suites at the five-star Grand Hôtel du Palais Royal. The experience includes four tickets to Balmain’s exclusive Ready-to-Wear show and four tickets to the house’s private party and cocktail reception. Guests will enjoy two hosted dinners and two lunches with a Balmain representative, unlocking behind-the-scenes insight into one of fashion’s most influential maisons. Every moment is designed for insider access, style and celebration. Back home, each couple receives a $10,000 gift certificate for a Balmain boutique in the U.S. city of their choice, extending the Parisian glamour long after the final runway walk. 

4:01 p.m.

Lot 33: Magic in Music City 

Winning bid: $320,000 

Total raised so far: $14.33 million 

Celebrate Nashville’s creative soul with fine wine, gourmet dining and an intimate live performance. Four couples will enjoy 2 nights in Music City, staying at a luxury hotel and savoring a private multicourse dinner at the home of Debbie and Noah McMahon of The Setting Wines, prepared by acclaimed Chef Selim Ülker and paired with rare wines and fine bourbon. The evening culminates in an exclusive acoustic concert with multi-platinum artist Mat Kearney. Another night features a tasting menu dinner with wine pairings at Yolan, one of Nashville’s most celebrated restaurants. Back home, each couple receives one magnum of The Setting Wines Rockpile Ridge Cabernet. Roundtrip private air from Naples to Nashville aboard a Challenger 300 or 350 is included. 

3:53 p.m.

Lot 32: Brush Creek Ranch Bound with Staglin Family Vineyard 

Winning bid: $600,000 

Total raised so far: $14.01 million 

Discover the romance of the American West paired with world-class cabernet and refined adventure. Two couples will enjoy a 5-night escape hosted by Shari and Garen Staglin, beginning with 1 night at St Julien Hotel & Spa in Boulder, Colorado, and a Michelin-starred wine-paired dinner at Frasca Food and Wine. Continue for 4 nights at the five-star Lodge & Spa at Brush Creek Ranch in Wyoming, featuring horseback riding, fly-fishing, a private hat fitting, a pasta class at The Farm and a Staglin-hosted dinner at Cheyenne Club. Each day blends rustic adventure with polished luxury. Back home, each couple receives six magnums of Staglin Family Vineyard Estate Cabernet Sauvignon. Roundtrip private air from Naples to Boulder and return from Saratoga, Wyoming, is included. 

3:47 p.m.

Lot 31: Million Dollar Meal…ALL for the Kids! 

Winning bid: $1 million 

Total raised so far: $13.41 million 

Turn generosity into an unforgettable culinary celebration that gives back to children in need. Forty couples will enjoy an exclusive evening at Prime Social Reserve in Naples on Nov. 17, 2026, featuring a multi-course dinner prepared by Michelin-recognized Celebrity Chef Dustin Valette, 2026 Chef de Cuisine, in collaboration with Executive Chef Alejandra Bringas. The evening begins with a cocktail and wine reception with passed hors d’oeuvres, followed by an elegant dinner expertly paired with fine wines. Guests will also enjoy live musical entertainment by award-winning singer-songwriter Kelly Neff, creating an immersive and memorable atmosphere. Back home, the true reward is the impact: Every dollar raised supports the Naples Children Foundation’s mission to transform the lives of children in Collier County.

3:43 p.m.

Lot 30: Gargiulo: A Journey Through Culinary Italy 

Winning bid: $650,000 

Total raised so far: $12.41 million 

Experience Italy through the lens of masterful cuisine, legendary wines and intimate access. Two couples will embark on a 6-night culinary journey hosted by Valerie Boyd and Jeff Gargiulo alongside Celebrity Chef Angelo Auriana. The adventure begins with a private planning dinner at the Gargiulo home in Naples before continuing to Italy for 4 nights in Bologna and Emilia-Romagna, featuring visits to Mercato di Mezzo and iconic producers of Parmigiano Reggiano, Prosciutto di Parma and balsamic vinegar of Modena, with daily regional lunches and dinners. Conclude with 2 nights in Bergamo led by Chef Auriana for private food tours and tastings. Back home, each couple receives three double magnums of etched 2022 Gargiulo Vineyards Cabernet Sauvignon. Roundtrip business-class airfare to Italy is included.

3:36 p.m.

Lot 29: Rev Up and Wine Down: Bespoke Napa Valley Indulgence 

Winning bid: $240,000 

Total raised so far: $11.76 million 

Shift effortlessly from supercar thrills to Michelin-starred elegance in Napa’s most indulgent playground. Four couples will enjoy 4 nights in luxury suites at the five-star Poetry Inn Napa Valley, hosted by Sullivan Rutherford Estate. Signature moments include a “Merlot Mastery” blind tasting with winemaker Jeff Cole, a private culinary experience with Loco Tequila pairings prepared by Michelin-starred Chef Rogelio Garcia and a multicourse dinner at 3-Michelin-starred The French Laundry served with J.O. Sullivan Founder’s Reserve wines. Additional highlights include a 90-minute spa treatment per person and a sports car driving experience with Napa Valley Car Club. Back home, each couple receives a 3-liter 2021 J.O. Sullivan Founder’s Reserve Cabernet Sauvignon, a vertical of Founder’s Reserve Merlot and three Loco Tequila expressions. 

3:30 p.m.

Lot 28: A Private Paradise Between the Pitons 

Winning bid: $420,000 

Total raised so far: $11.52 million 

Escape to a Caribbean sanctuary where luxury, privacy and natural beauty meet in perfect harmony. Four couples will enjoy 4 nights at La Belle Hélène, a 13,000-square-foot private villa in St. Lucia featuring 10 ensuite bedrooms, expansive indoor-outdoor living, a lagoon pool and full access to Windjammer Landing amenities. Signature inclusions include a multicourse in-villa welcome dinner paired with fine wines, family-style breakfasts, a full-day private catamaran charter and personalized concierge service by Parea Travel. Relax on floating pontoons, explore secluded coves or unwind in the villa’s private courts, gardens and sunset-view lounges. Back home, the experience lingers as a once-in-a-lifetime island retreat. Roundtrip private air from Naples to St. Lucia aboard a Challenger 300 is included.

3:23 p.m.

Lot 27: Miami Grand Prix: Fast Cars and Napa Classics 

Winning bid: $350,000 

Total raised so far: $11.1 million 

Feel the adrenaline of Formula 1 paired with collector-caliber Napa wines in a high-octane Miami escape. Two couples will enjoy 3 nights at the five-star Nobu Hotel Miami Beach from May 1–4, 2026, with four exclusive passes to The 72 Club, the elite trackside lounge overlooking Turn 4 and the podium at the Miami International Autodrome. Enjoy panoramic race views, premium cuisine, luxury hospitality and seamless planning by a dedicated concierge team at Parea Travel. From pre-race celebrations to post-race revelry, every detail is elevated. Back home, each couple receives a curated collection of large-format and standard bottles from Heitz Cellar, Burgess, Stony Hill, Ink Grade and Haynes Vineyard, extending the thrill of race weekend long after the checkered flag waves. 

3:18 p.m.

Lot 26: Where Cabernet Elegance Meets Riviera Shores 

Winning bid: $420,000 

Total raised so far: $10.75 million 

Blend Napa’s most elegant cabernet with Riviera-style indulgence in one seamless escape. Four couples will enjoy 5 nights in Mexico at Rosewood Mayakoba, staying in an Exclusive Resorts four-bedroom villa featuring 6,000 square feet, a private pool, ensuite bedrooms and personalized concierge service. Highlights include a private chef dinner with Darioush wine pairings, a half-day fishing excursion or VanDutch 56 yacht charter and a $5,000 resort credit. At a separate time, winners will enjoy an intimate wine-paired dinner at Darioush Winery in Napa hosted by Shahpar and Darioush Khaledi. Back home, each couple receives a vertical collection of Darioush Darius II Cabernet Sauvignon in magnums plus one double magnum. Roundtrip private air from Naples to Cancún aboard a Citation Sovereign is included.

3:12 p.m.

Lot 25: An Oasis of BVLGARI Wonders in Dubai 

Winning bid: $650,000 

Total raised so far: $10.33 million 

Indulge in Arabian opulence where couture, cuisine and desert adventure converge. Two couples will enjoy 5 extraordinary nights in Dubai with luxury accommodations at the five-star Bvlgari Resort Dubai. Signature experiences include a private yacht charter with lunch on the Persian Gulf, a guided full-day Abu Dhabi tour featuring Sheikh Zayed Grand Mosque, Louvre Abu Dhabi and Qasr Al Watan and a luxury desert safari capped by a sunset dinner. Additional highlights include a Signature Hammam treatment, private tours of Old Dubai and Alserkal Avenue, a private BVLGARI high jewelry appointment and gourmet dining at Michelin-starred Il Ristorante by Niko Romito and STAY by Yannick Alléno, plus Pierchic and Bvlgari Resort restaurants. Back home, the memories shine brightest, while the experiences redefine luxury travel. 

3:07 p.m.

Lot 24: Grace & Grandeur with Domaine Serene 

Winning bid: $380,000 

Total raised so far: $9.68 million 

Go behind the velvet rope of Oregon wine, where hospitality is private and the pours come from deep in the library. Two couples will enjoy 5 nights in the Dundee Hills with accommodations at the private Domaine Serene Winery Hill House. Signature inclusions begin with a garden tour and a private multicourse dinner hosted by proprietor Grace Evenstad, plus private tastings of Domaine Serene, Maison Evenstad and Château de la Crée wines. The itinerary also features a library tasting in Portland, a chef’s pairing dinner in Lake Oswego and a VIP estate tour that includes a blending session with the winemaker. For a change of pace, enjoy a deep-sea fishing excursion off the Oregon Coast. Back home, the winners receive a collection of Domaine Serene, Maison Evenstad and Château de la Crée wines in large-format and standard sizes, plus roundtrip business-class airfare to Portland. 

3:04 p.m.

Lot 23: Vistas & Vintages: Continuum in the Smoky Mountains 

Winning bid: $400,000 

Total raised so far: $9.3 million 

Pair Appalachian serenity with Mondavi-led hospitality and finish with a Napa feast few ever see. Three couples will enjoy a 6-night retreat in Tennessee, starting with 3 nights at Blackberry Farm featuring a private multicourse dinner with curated beverages, an adventure activity and spa treatments. Continue with 3 nights at Blackberry Mountain, highlighted by a private wine-paired dinner hosted by Tim Mondavi or Carissa Mondavi, a group mixology class and additional spa time. The experience culminates with a multicourse wine-paired dinner at Continuum Estate in Napa, hosted by a Mondavi family member. Back home, the winners receive a collection of Continuum and Sentium wines in large-format and standard bottles. Roundtrip private air from Naples to Walland, Tennessee, on a Phenom 300 is included. 

2:58 p.m.

Lot 22: Sonoma Sojourn with Browne Family Wines 

Winning bid: $280,000 

Total raised so far: $8.9 million 

This is Sonoma with the keys handed over: private estate living, chef-driven dining and a piano lot built for collectors. Two couples will enjoy 6 nights, including 4 nights in executive suites at the Browne Family Wines Estate and 2 nights at Appellation Healdsburg. Signature moments include an intimate chef-prepared dinner at the estate paired with CIRQ and CHEV wines, a multicourse tasting menu at Valette prepared by 2026 Chef de Cuisine Dustin Valette and hosted by proprietors Sarah and Michael Browne, plus a farm-to-table dinner at Charlie Palmer’s Folia. Additional highlights include a choice of golf or spa treatments at Mayacama. Back home, winners receive a remarkable 110-bottle piano lot of CIRQ and CHEV wines in formats ranging from 5 liters to 375 ml. 

2:52 p.m.

Lot 21: The Art of Sicily with Tasca d’Almerita 

Winning bid: $450,000 

Total raised so far: $8.62 million 

Live Sicily as insiders, with estate time, hands-on traditions and Etna’s dramatic edge. Two couples will enjoy 5 nights in Sicily, beginning with 3 nights at the historic Regaleali estate in Contrada Regaleali with private tastings, hands-on Sicilian cooking and ceramics classes, a scenic picnic lunch and family-style dinners paired with Tasca d’Almerita wines. Then continue for 2 nights at San Domenico Palace, a Four Seasons Hotel in Taormina, with visits to the Tascante estate, Mount Etna and a vineyard lunch. The itinerary blends culture and cuisine with the kind of access that turns a trip into a story worth retelling. Back home, the winners receive a curated collection of Tasca d’Almerita wines in magnum and standard sizes, ready to reopen Sicily with every pour. 

2:49 p.m.

Lot 20: Take the Gamble: From Oakville to Europe’s Shores 

Winning bid: $320,000 

Total raised so far: $8.17 million 

Start with Oakville’s most intimate tastings, then sail Europe with Ritz-Carlton-level ease. Two couples will enjoy 4 nights in Napa at Gamble Estates’ guest house in Oakville, featuring private tours and tastings at Gamble Estates, Seven Apart, Rudd Estate, Memento Mori and Greer Wine, plus multicourse wine-paired dinners hosted by estate proprietors. Then continue with a 9-night voyage aboard The Ritz-Carlton Yacht Collection’s Evrima from Lisbon to Dublin, with calls in Porto, A Coruña, Bordeaux, Plymouth and Cobh. All-inclusive dining, premium beverages and personalized service from a suite ambassador keep the experience seamless from port to port. Back home, each couple receives a 3-liter bottle of 2022 Gamble Estates Oakville Cabernet Sauvignon, a cellar centerpiece that matches the scale of the journey. 

2:44 p.m.

Lot 19: Luxury and Wildlife on the African Savannahs 

Winning bid: $650,000 

Total raised so far: $7.85 million 

Trade boardrooms for big skies on a Belmond safari that pairs city glamour with bucket-list wildlife. Two couples will enjoy 9 nights in Africa, beginning with 3 nights in junior suites at Mount Nelson, A Belmond Hotel, Cape Town, including a Jeep wine country tour, a cabana day and dinner at Amura by Ángel León. Then fly to Botswana for 3 nights in luxury tented rooms at Eagle Island Lodge, A Belmond Safari, in the Okavango Delta, with twice-daily game drives, a mokoro water tour, boating, fishing and inclusive meals. Continue for 3 nights at Savute Elephant Lodge, A Belmond Safari, in Chobe National Park, with game drives, a San Bushman rock art hike, a baobab grove visit and a pop-up helicopter dinner. Back home, the story is the souvenir, and roundtrip business-class airfare from the U.S. to Cape Town plus highest-class airfare to Maun is included. 

2:38 p.m.

Lot 18: From the Vineyards of Chile to the Heart of Napa 

Winning bid: $260,000 

Total raised so far: $7.2 million 

Chase bold Chilean terroir, then finish with a classic Napa homecoming built around library wines. Two couples will enjoy an 8-night journey beginning with 2 nights in Santiago in Grand Terrace Suites at the Mandarin Oriental, including a Maipo Valley wine tour with tasting at Doña Paula and a multicourse dinner at Boragó. Continue for 3 nights at VIK Chile in Puro VIK bungalows with a private vineyard tour, cooking class, gourmet dining and resort activities from hiking to horseback riding. Then conclude with 3 nights in Napa at Southbridge, featuring dinner at Goose & Gander, an estate multicourse dinner hosted by proprietor Beth Novak with an exclusive library tasting and a tour and tasting at Spottswoode. Back home, the winners receive a curated collection of Spottswoode Estate wines in magnum and standard sizes. Roundtrip business-class airfare to Chile is included. 

2:34 p.m.

Lot 17: Spirit of The Bahamas 

Winning bid: $550,000 

Total raised so far: $6.94 million 

This is the Bahamas at full throttle: private yacht living followed by resort-level luxury in a festival co-chair’s home. Four couples will enjoy 8 nights in The Bahamas, starting with 5 nights aboard the 115-foot M/Y Spirit, featuring 5 ensuite cabins, a Jacuzzi, water toys, chef-prepared meals and a crew of 6 to handle every detail. Spend your days island-hopping, snorkeling, fishing or simply unplugging on deck. Then shift ashore for 3 nights at the Albany Bahamas residence of 2026 festival co-chairs Ashley and Adam Gerry, a 6-bedroom home with a terrace plunge pool and marina views, plus dining at three resort restaurants, one round of golf per person, spa treatments and full access to Albany amenities. Back home, the memories are the treasure, and roundtrip private air from Naples to The Bahamas on a Citation Longitude is included. 

2:28 p.m.

Lot 16: Living Italy, One Sip at a Time 

Winning bid: $500,000 

Total raised so far: $6.39 million 

Turn Italy into your personal tasting trail, from Verona to the Tuscan coast to Brunello country. Three couples will enjoy 9 nights across Verona, Bolgheri and Montalcino, beginning with 4 nights at Relais Villa Della Torre in Verona with Michelin-starred dining, private touring and a cooking class, plus a helicopter transfer to Bolgheri with a stop at the Ferrari Museum. Spend 3 nights in Bolgheri featuring seaside dining at La Pineta, a Tuscan barbecue under the stars and a private boat tour to Elba Island, plus village visits. Conclude with 2 nights at the San Polo estate in Montalcino with vineyard experiences and a farewell wine-paired dinner featuring Marilisa Allegrini wines. Back home, the winners receive 6 magnums from Marilisa Allegrini estates. Roundtrip business-class airfare to Italy is included. 

2:22 p.m.

Lot 15: From Courtside Power to Mountain Precision 

Winning bid: $260,000 

Total raised so far: $5.89 million 

Get closer than most fans ever will, then craft a Napa cabernet that’s truly yours. Three couples will enjoy 4 nights in California, beginning with 1 night at Four Seasons San Francisco and ultra-premium seats at Chase Center for a Golden State Warriors game, joined by NBA legends Isiah Thomas and Chris Mullin and Cardinale winemaker Chris Carpenter. VIP access includes photo opportunities and a postgame private dinner at Miller & Lux. Then continue to Napa for 3 nights at the Manzanita Guest House, where the group will blend a custom Cardinale Cabernet and enjoy a private chef dinner hosted by proprietor Barbara Banke, plus a fireside chat with her son, Christopher Jackson. Back home, the winners receive etched, signed magnums and standard bottles of their custom Cardinale wine. 

2:15 p.m.

Lot 14: The Best of Paris and Bordeaux in One Week 

Winning bid: $450,000 

Total raised so far: $5.63 million 

Design high jewelry in Paris, then toast it with Bordeaux’s most iconic pours. One couple will enjoy 7 nights split between Paris and Bordeaux with Cos d’Estournel and Messika, starting with 5 nights in a junior suite at La Réserve Paris. Signature inclusions include exclusive access to Maison Messika’s Haute Joaillerie Atelier, a private meeting with founder Valérie Messika and the opportunity to design a bespoke high jewelry piece, plus experiences such as a behind-the-scenes tour of the Opéra Garnier and a private Riva yacht cruise on the Seine, paired with Michelin-starred dining. Continue for 2 nights at La Maison d’Estournel with private tours, tastings and elegant wine-paired dinners at the estate. Back home, the winners receive a 5-liter 2018 Cos d’Estournel. Roundtrip business-class airfare and business-class train transfers between Paris and Bordeaux are included. 

2:11 p.m.

Lot 13: Sonoma’s Finest with Aperture and Chef Valette, Colorado High-Life with Cuvée Luxury Villas 

Winning bid: $400,000 

Total raised so far: $5.18 million 

Pair a winemaker’s insider Sonoma weekend with a Cuvée-powered mountain retreat and a cellar-sized payoff. Three couples will enjoy 3 nights in Healdsburg with VIP access at Aperture, including a blending session with winemaker Jesse Katz and a farmer’s market tour and cooking class with 2026 Chef de Cuisine Dustin Valette. Signature moments include dinner at The Matheson paired with Aperture wines, a whiskey tasting, golf at Mayacama, visits to Stonestreet and Vérité, plus dinner at Valette. Then retreat for 5 nights to Cuvée’s West Wing Penthouse at The Ritz-Carlton, Bachelor Gulch, with ski-in/ski-out access and an in-residence chef dinner. Back home, the winners receive 3 double magnums and 3 magnums of Aperture Cabernet, plus 15 cases of their custom-blended wine. Roundtrip private air from Naples to Eagle, Colorado, is included. 

2:04 p.m.

Lot 12: Château Life: An Exclusive Bordeaux Journey 

Winning bid: $600,000 

Total raised so far: $4.78 million 

Take over a Grand Cru dream: a private château stay with tastings that are typically off-limits. Five couples will spend 5 nights in Bordeaux with exclusive access to Château Troplong Mondot in Saint-Émilion, enjoying a private château with 5 bedroom suites, a pool, electric bicycles and sweeping vineyard views. With The Bordeaux Concierge, winners will receive 3 days of private visits and tastings at 6 Grand Cru Classé estates, including hosted lunches at 3 properties. Signature moments include an in-depth immersion tour and tasting of Troplong Mondot’s celebrated vintages, a countryside-style dinner in the orchard prepared by the Michelin-starred estate restaurant and a special dinner at Michelin-starred Les Belles Perdrix. Back home, each couple receives 1 magnum of 2019 Château Troplong Mondot. 

1:58 p.m.

Lot 11: Tasting the 800-Year Legacy of Del Dotto 

Winning bid: $260,000 

Total raised so far: $4.18 million 

Live inside Napa luxury while tasting one of the valley’s most storied family legacies. Four couples will enjoy a 5-night VIP stay centered on Del Dotto Vineyards, with accommodations at Villa Piazza in Yountville, featuring 4 king bedrooms with ensuites, multiple lounges and outdoor living with a bocce court, fire pit, pool, hot tub and panoramic vineyard views. The itinerary includes 2 full days of curated tours and tastings with options such as Amizetta, Gemstone, Girard and Peter Michael, plus a private Del Dotto Estate barrel tasting hosted by the family. Culinary highlights include a multicourse tasting menu dinner at 3-Michelin-starred The French Laundry and a private lunch in the Piazza Del Dotto winery garden paired with library wines. Back home, take a collection of etched Villa Del Lago and Del Dotto single-cluster and family reserve cabernets from 2012-2021. 

1:53 p.m.

Lot 10: The Sun-Drenched Paradise of Puglia with Black Book Villas 

Winning bid: $450,000 

Total raised so far: $3.92 million 

Claim the kind of Italian villa week that feels like a private resort booked just for your closest friends. Four couples will enjoy 7 nights at Villa Dusenszky Vitale by Black Book Villas in Puglia, a five-star estate offering 9 bedrooms, 15 bathrooms, indoor and outdoor pools, a hammam, spa, tennis court and 57 acres of gardens and olive groves. Signature inclusions bring the region to life, from an in-villa pizzica music and dance experience to a mozzarella-making demonstration with aperitivo, a hands-on cooking class, a local winery visit and a dinner at a neighborhood trattoria. Between events, explore whitewashed hill towns and trulli villages, stroll centuries-old groves or join the September vineyard harvest. Daily housekeeping, chef, waiter and luxury concierge services are included for a seamless stay. 

1:48 p.m.

Lot 9: The Ultimate Invitation: CHANEL 2026 High Jewelry Collection at La Pausa 

Winning bid: $480,000 

Total raised so far: $3.47 million 

Enter a world where access is the luxury, and the guest list is the prize. One couple will enjoy 4 nights on the French Riviera with exclusive access to the unveiling of the CHANEL 2026 High Jewelry Collection at Villa La Pausa from May 6-10, 2026. Stay in a luxurious suite at the five-star Grand-Hôtel du Cap-Ferrat, A Four Seasons Hotel, and attend CHANEL’s premier high jewelry events, including a welcome cocktail, black-tie gala dinner and private viewing of the new collection. The Maison will curate select meals and experiences tailored to the couple’s preferences, delivering a bespoke Riviera itinerary shaped around style, culture and celebration. Roundtrip business-class airfare to France is included. 

1:42 p.m.

Lot 8: Scaling the Heights of the Promontory Territory 

Winning bid: $400,000 

Total raised so far: $2.99 million 

Own a perfect-score Napa vertical and pair it with access money can’t typically buy. Three couples will enjoy a 2-night getaway at five-star Relais & Châteaux Meadowood, including a spa treatment for each guest. The signature experience is exclusive access to Promontory’s remote territory, featuring a private tour and tasting with winemaker David Cilli and a multicourse, library wine-paired dinner prepared by 3-Michelin-starred Chef Christopher Kostow, hosted by Amanda Harlan and Will Harlan. The cellar component is extraordinary: a rare vertical of 6 double magnums of Promontory vintages from 2013-2018, each a perfect 100-point wine and a cornerstone addition to any serious collection. 

1:37 p.m.

Lot 7: A Tale of Two Wine Worlds: France and California 

Winning bid: $500,000 

Total raised so far: $2.59 million 

Live the rare double life of two iconic wine regions, hosted by the families behind them. Two couples will enjoy 8 nights split between Bordeaux and Napa, courtesy of Florence and Daniel Cathiard of Château Smith Haut Lafitte and Cathiard Vineyard. In Bordeaux, spend 3 nights at five-star Les Sources de Caudalie with lunch at the Cathiards’ home, a “Caviar from Sea to Soil” tasting, Signature Caudalie Ritual spa treatments and dinner at 2-Michelin-starred La Grand’Vigne, then continue for 2 nights at the Cathiards’ private waterfront Lodge SHL Cap-Ferret with a pinasse boat outing. In Napa, stay 3 nights at five-star Relais & Châteaux Meadowood in Treeline Suites, capped by a VIP Cathiard Vineyard tour and a multicourse dinner hosted by winemaker Justine Labbé at the Cathiard private home. Back home, each couple receives signed magnums from both estates. 

1:29 p.m.

Lot 6: The Jewels of Biondi-Santi and the Gems of Fratelli Piccini 

Winning bid: $350,000 

Total raised so far: $2.09 million 

Treat yourself to Tuscany at its most refined: art, jewelry and Brunello with insider access. Three couples will enjoy 6 nights hosted by Biondi-Santi and Fratelli Piccini, beginning with 2 nights at The Place Firenze featuring private atelier time at Fratelli Piccini, select cultural visits and a welcome dinner, plus a €10,000 jewelry credit per couple. Continue through Chianti for 1 night at Castello di Ama with private tours, art and wine, then 1 night in Montalcino at La Posta. The Biondi-Santi centerpiece includes a vineyard walk, library visit and lunch with CEO Giampiero Bertolini. Return to Florence for 2 additional nights with a guided Uffizi tour and a closing dinner. Back home, each couple receives a “Collection La Riserva” box of Biondi-Santi Brunello di Montalcino Riserva. 

1:23 p.m.

Lot 5: 20 Years of Alpha Omega: Celebrating Around The World 

Winning bid: $350,000 

Total raised so far: $1.74 million 

This is a milestone celebration that jumps from Napa’s most coveted vineyards to a private world at sea. One couple plus a guest couple will spend 3 nights in Napa hosted by Alpha Omega’s Michelle and Robin Baggett, with private vineyard tours, barrel tastings, a progressive Beckstoffer Vineyard tasting, a farm-to-table wine-paired lunch and a 20th anniversary dinner poured from library depths. Then trade land for legend with 14 nights aboard The World, Residences at Sea in a luxurious residence featuring a primary bedroom plus a second interior bedroom, with an in-residence chef dinner, 60-minute spa treatments, a vertical wine tasting with the ship’s sommelier and all meals and beverages included. Back home, enjoy a remarkable Alpha Omega collection highlighted by 2 double magnums of the 20th anniversary flagship ERA and 20 assorted Beckstoffer single-vineyard cabernets. 

1:17 p.m.

Lot 4: The Spirit of Argentina: From Tango to Terroir 

Winning bid: $500,000

Total raised so far: $890,000

Go from tango lights to mountain vineyards in a perfectly paced Argentina adventure. Two couples will enjoy 6 nights split between Buenos Aires and Mendoza, starting with 2 nights at a five-star boutique hotel paired with guided cultural touring, a private tango lesson and tickets to the Rojo Tango show at the Faena Hotel. Continue to Mendoza for 2 nights in a luxury suite with massages, tea service and a Michelin-starred dinner paired with Catena Zapata wines, then finish with 2 nights at the Catena family’s private estate, Casa La Vendimia, for exclusive wine experiences and gourmet dining at Michelin-starred Azafrán and Angélica Cocina Maestra. Back home, each couple receives a cellar collection including large-format bottles. Roundtrip business-class airfare to Argentina and highest-class airfare between Buenos Aires and Mendoza are included. 

1:12 p.m.

Lot 3: Montalcino Dreaming 

Winning bid: $240,000

Total raised so far: $890,000

Claim a Tuscany escape built for serious wine lovers who want access, not crowds. Two couples will spend 5 nights in Montalcino with accommodations in the 2-bedroom Dimora Orto Apartment at Argiano Dimore. The trip includes a private VIP tour and tasting at Argiano hosted by the CEO, winemaker or agronomist, plus private tastings at Altesino and Caparzo. Signature dining moments range from a gourmet lunch and a 4-course wine-paired dinner prepared by Chef Elena Montini at Sala Ara Jani to a multicourse, wine-paired evening at the 2-Michelin-starred Ristorante Campo del Drago at Rosewood Castiglion del Bosco, plus a hands-on cooking class with Chef Montini. The lot also includes a large-format collection of estate wines for each couple and roundtrip business-class airfare to Italy. 

1:08 p.m.

Lot 2: In the Footsteps of a Queen with Rare Champagne 

Winning bid: $350,000

Total raised so far: $650,000

Step into royal history and rare bubbles with a Paris-and-Champagne immersion few can touch. Two couples will enjoy 6 nights in France, beginning with 3 nights at Grand Hôtel du Palais Royal in Paris, including a private Versailles tour with access to Queen Marie Antoinette’s private apartment, lunch at Ducasse au Château de Versailles and a private visit to the Mellerio jewelry boutique. Then continue for 3 nights at the historic Résidence Eisenhower in Champagne for private vineyard and cellar tours at Rare, a Reims Cathedral visit and a multicourse dinner featuring a vertical tasting of Rare Champagne from 1985-2015. Back home, each couple receives a magnum of Rare Millésime 2008 and Rare Rosé Millésime 2014, plus roundtrip business-class airfare. 

1:04 p.m.

Lot 1: A Road Classic and Vineyard Jewels 

Winning bid: $300,000

Total raised so far: $300,000

Own a head-turning collectible that pairs rugged heritage with cellar-worthy prestige. Take home the 1991 Land Rover Vineyard Series Defender 90: Chardonnay 20-6IX, rebuilt with a 300 TDI engine and finished in Chawton White with Mandarin Italian Nappa leather, bespoke wood flooring and a custom rear wine case. The cellar component is equally outsized: 31 large-format bottles from 2026 Naples Winter Wine Festival vintners, anchored by an extremely rare 6-liter 2016 Biondi-Santi Brunello di Montalcino Riserva. The collection also includes magnums from standouts such as Alpha Omega, Cardinale, Château Smith Haut Lafitte, Continuum, Cos d’Estournel, Dalla Valle, Domaine Serene, Gargiulo, Promontory, Rare Champagne and Vega Sicilia. 

The Naples Winter Wine Festival returns Jan. 30–Feb. 1 to The Ritz-Carlton Naples, Tiburón, with the event’s signature live auction set for 1 p.m. Jan. 31. Now in its 26th year, the festival is one of the world’s most prestigious charity wine auctions, pairing rare vintages, elite culinary experiences and ultra-luxury travel with a philanthropic mission that directly benefits children and families in Collier County.

Since its launch in 2001, the festival has raised more than $336 million through the Naples Children Foundation, supporting programs focused on health care, education and social services for vulnerable children.

The 2026 festival follows a record-setting year. In 2025, fundraising surpassed $34 million, exceeding the previous annual record and underscoring Naples’ status as one of the nation’s most generous philanthropic communities. Organizers say this year’s auction lineup is designed to build on that momentum, featuring a curated slate of once-in-a-lifetime offerings that blend global travel, private access and exceptional wine.

“Our team has worked throughout the year with our generous donors and loyal supporters in curating some truly remarkable wine, food and travel experiences for this year’s live auction,” said Joe Matina, a Naples Children Foundation trustee and auction lot committee member. “We anticipate that these unique experiences will encourage our patrons to bid high and bid often.”

The live auction catalog spans a wide range of experiences, from immersive journeys through iconic wine regions and private villa retreats to luxury yacht voyages, major sporting events and exclusive cultural invitations. Many lots feature insider access, including private tastings and hosted dinners at renowned estates, behind-the-scenes tours and curated itineraries led by celebrated vintners, chefs and hosts. Several offerings also include collectible wine components, with magnums, double magnums and rare library selections designed to anchor serious cellars and milestone celebrations.

“These latest auction lots pair the world’s most exotic travel experiences with the very best in food and wine,” said Valerie Gargiulo, a Naples Children Foundation trustee and auction lot committee member. “All funds raised during the live auction will help us create lasting change by investing in proven programs that transform the lives of the most vulnerable children in our community.”

Festival leaders say the auction’s success reflects months of collaboration among donors, volunteers and staff. “Thanks to our generous donors and loyal supporters, our team has been able to assemble some truly amazing wine, food and travel experiences for this year’s live auction,” said Ashley Gerry, 2026 Naples Winter Wine Festival co-chair and an auction lot committee member. “We anticipate that these incredible opportunities will encourage festival attendees to bid high and bid often.”

Gulfshore Business Senior Editor Tim Aten will provide real-time coverage from inside the auction tent, reporting winning bids for each lot and tracking a running total of money raised throughout the evening. Updates will be posted as the live auction unfolds, offering readers a detailed look at how the day’s bidding progresses and how quickly the total climbs.

Proceeds from the festival benefit the Naples Children Foundation, which supports a broad range of programs serving children and families across Collier County, with a focus on long-term impact and measurable outcomes.