2023 Auction Lots

Below is a listing of the amazing 2023
Naples Winter Wine Festival auction lots

Flexjet Raffle 2023

Ultimate eight (8) night Kentucky Derby and the heart of horse country experience for two (2) couples on Thursday, May 4–Friday, May 12, 2023

Roundtrip, Private Air on a Bombardier Learjet via Northern Jet Management from Naples, Florida to Louisville, Kentucky and returning from Lexington, Kentucky for two (2) couples
Private ground transportation to stated activities in Louisville and from Louisville to Lexington

Louisville, Kentucky:
Three (3) nights’ accommodations in Club Luxury rooms at The Brown Hotel for two (2) couples
Four (4) tickets to the Mansion at Churchill Downs during the Kentucky Oaks on Friday, May 5, 2023 and the Kentucky Derby on Saturday, May 6, 2023
Mansion tickets include insider access to Churchill Downs, personal concierge, private entrance, chef-prepared meals, alcoholic and non-alcoholic beverages and no wait wagering
VIP tour of Makers Mark and Beam Suntory, followed by lunch
Two (2) whiskey baskets with the winners’ choice of whiskey

Lexington, Kentucky:
Five (5) nights’ accommodations and exclusive use of Stonegate Farm private residence
Stonegate Farm features a four (4) bedroom main house, a guest house, pool, gym and tennis courts and is situated on 200 scenic acres
One (1) hour tour of Stonestreet Farm followed by a meet and greet with champion thoroughbred Rachel Alexandra while enjoying wine and hors d’oeuvres
Exclusive guided driving tour of Hill ‘n’ Dale at Xalapa and visit with stallions, including the renowned winning stallion, Curlin
Four (4) 90-minute facials and four (4) 90-minute massages at About Face Organic Skincare Studio
One (1) dinner at Castle Farm at The Kentucky Castle


Whether you’re a fan of thoroughbred racing, a clothes horse, a bourbon lover or an adrenalin addict, the only place to be on the first Saturday in May is Churchill Downs in Louisville.

The winning bidder’s party of four will experience the best of the Kentucky lifestyle during eight enchanted days in May. You’ll begin in Louisville, where you’ll spend three nights in Club Luxury rooms at the historic The Brown Hotel.

You’ll attend both the Derby and Friday’s Kentucky Oaks (a stakes race for three-year-old fillies) with tickets to the supremely private Mansion at Churchill Downs, which has eclipsed Millionaires Row as the most coveted place to watch the races.

In fact, the Mansion is so exclusive that most visitors to the track don’t even know it exists, given its secret, high-security location. Even the Louisville elite can’t buy tickets to the Mansion—they need to be invited and make a three-year commitment. As soon as you arrive, your assigned concierge will greet you and transport you in a golf cart toward the Churchill Downs red carpet. You’ll be presented with a glass of Champagne for the ride up in the private elevator and escorted through the heavily guarded, hidden door. Inside, there are food stations and bars manned by chefs and bartenders flown in from all over the country.

You can watch the races from your covered balcony, or feel free to visit the Paddocks and trophy display. A personal concierge will make sure you have effortless access to food, drinks and wagering.

While in Louisville, you’ll take advantage of the city’s proximity to the nearby Bourbon Trail to visit two of the area’s leading bourbon distilleries and receive VIP tours at both Maker’s Mark and Beam Suntory.

With memories of the Kentucky Derby still fresh in your mind, you’ll travel to Lexington for a five-night stay at Stonegate Farm, located next door to Woodford Reserve and minutes away from Keeneland and Kentucky Horse Park. Magnificent and private, the 200-acre estate includes a pool, pool house, gym and tennis courts. Your party will have exclusive use of the residence, with a main house that sleeps eight guests comfortably.

You’ll have a guided driving tour of Hill ‘n’ Dale Farms, a renowned horse breeding ranch with a roster of world-class stallions and clients based in nearby Xalapa. You’ll be able to spend some time with thoroughbreds during your visit, including the famous Curlin, the highest North American money earner, whose racing wins included the 2007 Preakness and Breeders’ Cup Classic.

Racing enthusiasts will be delighted at the opportunity to tour Stonestreet Farms in Versailles, the thoroughbred ranch founded by famed vintner Jess Stonestreet Jackson. Jackson approached horse breeding with the same combination of pragmatism and passion that he brought to winemaking. In 2009, he acquired a majority interest in the filly Rachel Alexandra after watching her win Kentucky Oaks by an astounding 20 lengths. While enjoying wine and hors d’oeuvres, you’ll meet the legendary horse in her stables0.

Each member of your party will be able to recharge their batteries; two guests will receive a Thai massage and two will receive a therapeutic massage plus a 90-minute luxury facial for all four guests at the About Face Organic Skin Care Studio in Lexington. Afterward, head for The Kentucky Castle outside Versailles, a 50-year-old castle on a hill with sweeping views of 100 acres of farmland, and savor a farm-to-table meal at the Castle Farm restaurant.

This magical eight-day journey provides the ultimate in thoroughbred racing and bourbon tourism, with ample opportunity for rest and relaxation. Raise your paddle high and start designing your Kentucky Derby hats today!

Insider's Info

Due to the nature of events in this trip, it is date specific and will take place Thursday, May 4-Friday, May 12, 2023. Roundtrip, Private Air from Naples, Florida to Louisville, Kentucky and returning from Lexington, Kentucky is included. In Louisville, Kentucky, winners will have a private car and driver to stated activities and ground transportation from Louisville, Kentucky to Lexington, Kentucky which will take approximately 80 minutes. Ground transportation is not included during the stay in Lexington, Kentucky. Stonegate Farm’s Main House offers four (4) bedrooms with a Master King bedroom, a Queen bedroom and two (2) bedrooms with Double Twins and Guest House includes two (2) bedrooms with Full beds. There is no housekeeping or staff at the private house. Gift certificates for Castle Farm and About Face Organic Skincare Studio must be presented at the time of service. Dinner at The Kentucky Castle is valid for four (4) people for a value of up to $200, wine and gratuities are not included. Reservations must be made in advance, and the certificate must be redeemed between Monday, May 8-Thursday, May 11, 2023. Four (4) 90-minute facials and four (4) 90-minute massages consisting of two (2) therapeutic massages and two (2) Thai massages are included. Due to the size of the facility, only two (2) winners can get services simultaneously. Services must be schedule at least two (2) weeks in advance and take place on the Monday through Thursday following the Kentucky Derby. Gratuities are not included for any portion of the trip and are the responsibility of the winning bidders.


About Face Organic Skincare Studio, Barbara Banke, Beam Suntory, Dr. Stephen & Penny Pomeranz and The Kentucky Castle

Private Air donated by Northern Jet Management

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