Join us on Friday, January 16, 2026 to bid on these extraordinary auction lots.
To learn more about registering, please contact Nenaly Patino or purchase tickets here.
We look forward to seeing you there!
Feast & Vintages
This exceptional wine lot features over twenty (20+) hand-selected bottles generously donated by members of our Board of Trustees – recently honored as one of the Top 6 Boards of Directors in Southwest Florida’s Philanthropy and Charitable Communities. Truly the best wines from the best people, this collection reflects both refined taste and extraordinary leadership.
Six chefs. Six courses. One extraordinary evening. Your experience continues with a private dinner hosted by Pam and Bill Dempsey for you and nine (9) guests at the prestigious Hideaway Beach Club. Take in the gorgeous ocean views as the sun sets, while savoring a six-course chef’s dinner featuring dishes created by six talented chefs, each bringing their own inspiration and signature style to the table. Together, they create an elevated dining experience that not only delights the palate but also supports a meaningful cause.
Your evening will be enhanced by a live performance by a star vocalist from Gulfshore Opera, accompanied by a pianist. This mesmerizing musical moment sets the tone for the night, creating an immersive atmosphere of refined entertainment as guests enjoy exceptional wine, exquisite food, and the promise of an unforgettable experience. Dinner will be held on a mutually agreed upon date in the spring or fall.
Generously donated by Guadalupe Center Board of Trustees and Pam & Bill Dempsey
Empires and Aegean Elegance
A journey from Istanbul to Athens
November 26 – December 7, 2026
Embark on an unforgettable eleven-day, ten-night luxury voyage for one couple aboard Regent Seven Seas Voyager, sailing through the legendary waters of the Aegean Sea. This remarkable journey blends ancient history, iconic destinations, and world-class comfort into one radiant experience.
Your adventure begins in captivating Istanbul, where you’ll enjoy one night of five-star pre-cruise accommodations, including airport transfers. Explore vibrant bazaars, historic palaces, and soaring minarets before setting sail across turquoise waters once traveled by empires and explorers. Over the course of the cruise—including two serene days at sea—you will visit extraordinary ports such as Izmir and Marmaris, Turkey; Limassol, Cyprus; Rhodes, Heraklion (Crete), and Mykonos, Greece, before concluding in Athens (Piraeus). Each destination offers a curated blend of ancient wonders, cultural treasures, and breathtaking coastlines.
Your Category H Deluxe Veranda Suite includes unlimited shore excursions, gourmet dining in all onboard restaurants, premium beverages, daily replenished in-suite minibar, unlimited WiFi, spa access, valet laundry service, prepaid gratuities, and 24-hour in-suite dining. A journey of elegance, discovery, and indulgence—where history and luxury sail in perfect harmony. International airfare not included.
Enhancing this extraordinary voyage, the auction lot also includes a Louis Vuitton Keepall Bandoulière 50, Mini Dopp Kit, and a matching scarf in ocean blue, graciously donated by Waterside Shops. Thoughtfully curated for elegant travel, these timeless accessories are the perfect companions for a journey spanning empires, islands, and the sapphire waters of the Aegean.
Graciously donated by Regent Seven Seas Cruises. Generously coordinated by Preferred Travel & Co.
30 Miles Out to Sea
Escape to Nantucket for a seven-day, six-night stay in a stunning private home, designed for three couples and available on a mutually agreed-upon date in 2026.
Just 30 miles offshore, Nantucket is a timeless New England treasure where coastal beauty, rich history, and relaxed luxury converge. Accessible by ferry or flight, this iconic island offers cobblestone streets, gaslit evenings, and a pace of life that invites you to truly unwind.
Your hosts, Darlene and Don DeMichele, welcome you to their magnificent five-bedroom private residence in the heart of Nantucket’s historic district, just steps from charming shops, renowned restaurants, and the celebrated Whaling Museum. Surrounded by one of the nation’s largest collections of pre-Civil War homes, you’ll be immersed in centuries of character and coastal elegance.
Spend your days exploring 82 miles of pristine beaches, from calm waters at Jetties Beach to the surf at Cisco and Surfside. Enjoy fishing, biking, lighthouse visits, or simply strolling past hydrangea-lined streets. Evenings invite unforgettable dining experiences, from iconic lobster rolls to award-winning cuisine.
This adult-friendly retreat promises serenity, connection, and unforgettable memories—where the magic of Nantucket lingers long after your stay.
Generously donated by Darlene & Don DeMichele
African Splendor: A Curated Safari Adventure
Safari • Wine • Cape Town
Experience the ultimate South African escape on this seven-day, six-night luxury journey for one couple, exclusively curated by Travel Sommelier and valid through January 17, 2027.
This tailor-crafted adventure seamlessly blends vibrant city life, world-class wine, and unforgettable Big 5 safari experiences. Begin with two nights in Cape Town, one of the world’s most breathtaking cities. Stay at the elegant Cape Cadogan, perfectly situated near Table Mountain and the waterfront. Explore the Cape Peninsula, Cape of Good Hope, penguin colonies, Robben Island, or enjoy optional shark diving.
Next, travel to the heart of the Cape Winelands for two nights in Franschhoek, South Africa’s culinary and wine capital. Enjoy luxury accommodations at Leeu House, surrounded by dramatic mountain views, exceptional dining, and access to some of the country’s most celebrated wineries.
Your journey culminates with three nights at Marataba Private Game Reserve, an exclusive Big 5 safari destination within the Waterberg Biosphere. Stay at Marataba Safari Lodge, where daily game drives, a private boating safari, and refined cuisine create an unforgettable wilderness experience.
A remarkable blend of adventure, indulgence, and natural beauty—crafted for travelers seeking Africa at its most extraordinary. International airfare not included.
Graciously donated by Travel Sommelier.
Moonlight in the Garden
Step into an unforgettable night where elegance, nature, and culinary artistry come together. Darlene and Don DeMichele invite you to an exclusive private dinner for 20 couples, hosted within the breathtaking beauty of the Naples Botanical Garden.
Crave Culinaire’s renowned Chef Brian Roland will personally curate an extraordinary multi-course menu crafted especially for this occasion, pairing innovation with the freshest seasonal flavors. To elevate the experience further, Knights Bridge Winery will generously provide a selection of exceptional wines, perfectly paired to each course and poured throughout the evening.
This is more than a dinner—it is a night of wonder, connection, and celebration set in one of Naples’ most spectacular sanctuaries.
Location: Naples Botanical Garden
Date: March 31, 2026
Generously donated by Darelene & Don DeMichele, wines donated by Knights Bridge Winery
Land of the Pharaohs
October 10 – October 17, 2026
Experience the wonders of ancient Egypt on this eight-day, seven-night luxury journey for one couple, personally curated by the President and CEO of Big Five Tours and Expeditions. From arrival to departure, every detail is designed for seamless comfort, privileged access, and unforgettable discovery.
Your adventure begins in Cairo with VIP airport assistance and luxury transfers, followed by a stay at the iconic St. Regis Cairo. Explore the legendary Pyramids of Giza, the Great Sphinx, and the extraordinary Grand Egyptian Museum, including exclusive access to select galleries not yet open to the public.
After two nights in Cairo, fly to Luxor, where a private Egyptologist leads you through the awe-inspiring Temple of Luxor, Karnak, and the Valley of the Kings and Queens, including a special visit to the tomb of King Tutankhamun. Then embark on a refined four-night Nile River cruise, sailing to Edfu, Kom Ombo, and Aswan while enjoying gourmet dining, afternoon tea, and elegant onboard celebrations.
Your journey concludes with a same-day flight to Abu Simbel to witness the monumental temples of Ramses II, before returning to Cairo for a luxurious stay at the Waldorf Astoria. A rare and immersive journey through history, culture, and timeless splendor. International flights not included; all in-country transfers and flights are included.
Enhancing this exceptional experience, the auction lot includes a $1,148 gift card to Lafayette 148. Perfect for elevating your travel wardrobe or indulging in timeless luxury, it is a stylish complement to this unforgettable journey.
Graciously donated by Big Five Tours & Expeditions. Generously coordinated by Preferred Travel & Co.
From Vine to Veranda
A Knights Bridge Getaway
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Escape to the heart of wine country for a three-night luxury stay at the newly renovated Bailey Vineyard House, nestled on the stunning Knights Bridge Estate Vineyard in Knights Valley, Sonoma. Designed for three couples, this intimate getaway offers privacy, elegance, and unparalleled access to some of the region’s most celebrated wines.
Wake to sweeping views of Mount St. Helena, enjoy peaceful vineyard walks, and unwind on the veranda as the sun sets over the valley. Your experience includes an exclusive Knights Bridge Winery tour and tasting, featuring a barrel tasting of the estate’s flagship wine, Draco Dormiere, and a first taste of their new, limited-release Chardonnay.
Indulge in a private chef-prepared dinner at the estate, thoughtfully paired with Knights Bridge wines, and capture unforgettable moments with a one-hour professional photo shoot on the property by renowned photographer Michael Larson. Additional highlights include a private tour and tasting at Brandon Gregory Estate and a memorable lunch at Chef Charlie Palmer’s Folia at the Appellation Hotel in Healdsburg.
Transportation to and from the airport, concierge services, taxes, and gratuities are included. International airfare not included. Experience must be scheduled on mutually agreeable dates and expires January 31, 2027.
Graciously donated by Knights Bridge Winery and Kelley & Jim Bailey.
Sunlit Stones and Sapphire Seas
Discover Puglia, Italy
Escape to the heart of Puglia for an eight-day, seven-night stay at the iconic Masseria Torre Coccaro, a beautifully restored 16th-century estate surrounded by olive groves and the sparkling Adriatic coast. Designed for one couple, this journey blends timeless Italian charm with refined luxury, including a Deluxe Room (377 sq ft) and luxury transportation throughout.
Balance curated experiences with free time to relax, explore independently, or indulge in the masseria’s world-class spa and cuisine. The adventure includes four private experiences:
- Valle d’Itria Discovery: Visit Ostuni, Alberobello, and Locorotondo with an expert guide, traveling in comfort through whitewashed villages and UNESCO-listed trulli.
- Mozzarella & Burrata Experience: Learn the secrets of Puglia’s celebrated cheeses with a private demonstration and tasting, followed by a leisurely lunch.
- Private Catamaran Cruise: Sail the Adriatic with a skipper and crew, enjoying crystal-clear waters, coastal views, refreshments, and relaxation.
- Baroque Lecce: Explore the “Florence of the South” with a private guide, marveling at ornate architecture and vibrant historic streets.
This exclusive escape offers the perfect blend of culture, cuisine, coastline, and countryside, delivering an authentic and luxurious immersion into southern Italy. International airfare not included.
Enhancing this exceptional Italian escape, the auction lot includes a $1,148 gift card to Lafayette 148. Ideal for curating an effortlessly chic travel wardrobe, it adds a refined touch to your journey through Puglia’s sunlit countryside and sapphire seas.
Graciously coordinated by Preferred Travel & Co.
Special Thanks to our Presenting Sponsor & Elevated Annual Partner
Thanks to all of our Gala Sponsors & Annual Partners
