2026 Auction Lots

Below is a listing of the amazing 2026
Naples Winter Wine Festival auction lots

Flexjet Raffle 2026

Four (4) night island escape to a luxurious private villa in St. Lucia for four (4) couples

Roundtrip, Private Air from Naples, Florida to St. Lucia on a Flexjet Challenger 300
Roundtrip private airport transfers

Four (4) nights’ exclusive use of the private villa La Belle Hélène by Windjammer Landing
La Belle Hélène features 13,000 sq. ft. of impeccable living space, ten (10) bedroom Suites with either King or Queen beds and ensuites, expansive indoor-outdoor living spaces, a private lagoon pool and a dedicated team to curate every detail
Full access to resort amenities at Windjammer Landing Resort & Residences, including pools, a private beach, a fitness center and non-motorized water sports
Full-day private catamaran charter, including light bites and select alcoholic beverages
Multi-course wine-paired in-villa welcome dinner prepared by a private chef
Family-style breakfast included each morning
Personalized concierge provided by Parea Travel

Picture a luxury retreat like no other, a world that combines beauty, privacy and every imaginable comfort—Red’s snapshots won’t begin to do it justice.

Four lucky couples will experience the indulgence of a lifetime, beginning in the sky aboard a Flexjet Challenger 300, where private air travel meets world-class comfort—because paradise should start the moment you leave the ground. Touching down in St. Lucia, guests are immediately immersed in the lush embrace of the island’s most sacred landscape. La Belle Hélène is not merely a villa—it is a destination rich in history, designed for discerning travelers seeking something truly special. This secluded waterfront estate is nestled between the Pitons and the Caribbean Sea, with a prime seafront position along the Queen’s Chain that no other property on the island can match. Whether you’re dining beneath flame-lit tiki lanterns, lounging on floating pontoons or waking up to the silhouette of the Pitons rising in golden morning light, La Belle Hélène offers an atmosphere that is both breathtaking and deeply personal.

Once the private Caribbean sanctuary of Lord Glenconner—a British aristocrat who brought global attention to St. Lucia—La Belle Hélène was a haven for royalty, rock stars and icons including Princess Margaret, Mick Jagger and David Bowie, a place where barefoot luxury met old-world eccentricity. Guests at La Belle Hélène are not just visitors: They become part of its living story. Every stay adds a new chapter, and guests are invited to craft an unforgettable chapter of their own.

The private estate features 10 bedrooms, including three private poolside bungalows with sea views. The Master Suite includes a private outdoor jacuzzi on its balcony, and three other bedrooms have their own separate living rooms. A personal butler, chef and housekeeping staff are included, serving breakfast, lunch, dinner and drinks on demand. Daily turndown service and 24/7 butler access ensure that every detail of your stay is flawlessly executed.

The property offers a range of unique amenities designed for both relaxation and recreation. A lagoon-style pool—the widest and deepest private villa pool in St. Lucia—features a dramatic fire pit, a jumping wall and a stone tower overlooking the sea. For sports and games, guests can enjoy indoor and outdoor table tennis, a pool table, cornhole, as well as private soccer, pickleball and basketball courts, all set on a waterfront terrace with jaw-dropping views of the Pitons.

Floating pontoons with private jetty access allow direct entry for swimming and snorkeling beneath one of the Caribbean’s most treasured marine sites. Complete with deck chairs and umbrellas, the pontoons provide unmatched relaxation framed by the island’s most iconic views.

Over 12 unique seating areas are scattered throughout the lush botanical gardens and sunset-view locations, many featuring fire pits, tiki lanterns and intimate lounges that offer a new way to experience the Pitons each day. The estate also provides direct access to Sugar Beach, a pristine white sand beach perfect for sunbathing, swimming or simply soaking in the Caribbean scenery, and guests will enjoy full access to all the amenities and features of the Windjammer Landing Resort.

The experience begins with a multi-course in-villa welcome dinner prepared by a private chef, warmly ushering guests into an unforgettable stay. Guests will also enjoy a full-day private catamaran charter, exploring St. Lucia’s sparkling waters. For those seeking further adventure, Parea Travel can assist with planning additional activities, from golf outings to island excursions, ensuring every detail of the visit is tailored to the guests’ desires.

This unique lot promises and delivers paradise on earth—Red urges you to bid as generously as possible and make the experience your own.

Insider's Info

This lot is for four (4) couples, but the villa can accommodate up to ten (10) couples. If the winning bidders choose to invite additional couples, the cost of airfare, airport transfers and any additional cost for the in-villa dinner and activities are at the winning bidders’ expense. This trip must be redeemed within twelve (12) months of the auction, for mutually agreeable dates and based on availability. Blackout dates for the villa include, but are not limited to, February 14-19; March 1-April 6; May 6-10; July 15-22; November 23-30; and December 19, 2026-January 2, 2027. Roundtrip, Private Air is included from Naples, Florida to Hewanorra International Airport on a Flexjet Challenger 300 or similar aircraft. Blackout dates for Private Air include, but are not limited to, February 5, 8, 13-17, 19 and 26; March 1, 6-8, 12-15, 20-22 and 27-29; April 3, 7, 10, 12 and 13;  May 2, 21, 22 and 25; June 19 and 22; July 2-6 and 29; August 27, 28 and 31; September 4, 6 and 7; October 8, 9 and 18; November 20-25 and 27-30; December 17, 19-23 and 26-31, 2026; and January: 1-6 and 18, 2027. Private Air must be redeemed by January 31, 2027. Flexjet requires a minimum of 30-days advance notice prior to your desired departure date and 48-hours prior notice for any changes to your flight itinerary. One (1) roundtrip group airport transfer in St. Lucia is included. Guests arriving or departing separately will be responsible for the costs of any additional transfers. A private chef will be available during the stay, but all costs of food and non-alcoholic beverages, except during the stated in-villa welcome dinner and daily family-style breakfast, are at the winners’ expense. Select alcoholic beverages, non-alcoholic beverages and light bites will be provided during the catamaran experience. Meals are only included as stated above. Alcoholic beverages are not included, other than during the catamaran experience and the select wine-pairings during the welcome dinner. Gratuities are not included for any portion of the trip and are the responsibility of the winning bidders.

Donor

La Belle Hélène by Windjammer Landing and Parea Travel
Private Air donated by Flexjet, LLC

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