2022 Auction Lots

Below is a listing of the amazing 2022
Naples Winter Wine Festival auction lots

Flexjet Raffle 2022

Three (3) night Kentucky Derby inside access experience from May 5 – May 8, 2022, for two (2) couples

Roundtrip, Private Air in a Phenom 300 from Naples, Florida to Louisville, Kentucky for two (2) couples

Three (3) nights’ accommodations in King Corner Suites at the Omni Louisville Hotel for two (2) couples
Four (4) tickets to a VIP pre-Derby party
Four (4) tickets to the exclusive, private Mansion at Churchill Downs during the Kentucky Oaks and the Kentucky Derby, with covered view and balcony over the finish line
Insider access to Churchill downs, including the Paddocks, trophy displays and more
Individual concierge to provide no wait access for all parts of the experience, including private entrance, food, beverages and wagering
Chef prepared meals and non-alcoholic and alcoholic beverages

Afternoon private tasting on either Thursday May 5th or Sunday May 8th of an exclusive selection of Old Carter and other rare whiskeys in downtown Louisville at the Old Carter Showroom
Two (2) Large Format whiskey bottles of Old Carter Whiskey
Original racehorse themed oil painting by equestrian artist, co-owner and founder, Sherri Carter
One (1) Hide Bag Co. Whiskey Tote
Two (2) $1,500 gift certificates toward custom hats made by Jenny Pfanenstiel of Formé Millinery Co., featured Milliner of the 148th Kentucky Derby


It’s been called “the most exciting two minutes in sports” and is nicknamed “the run for the roses”—a reference to the blanket of 554 red roses draped on the winning jockey at the end of the race. The Kentucky Derby is both the premier horse race in America and the high point of Louisville society. It has been held every year since 1875, throughout the Depression and the two World Wars.

Before you arrive, prepare for your trip by creating a custom hat in coordination with Master Milliner, Jenny Pfanenstiel, owner of Formé Millinery Co. Internationally recognized for her craft of hand creating and sculpting hats using the highest quality of materials found all over the world, she is a “Featured Milliner” of the Kentucky Derby and is the 2nd Milliner to ever be featured by Churchill Downs in the history of its racing. In addition to incorporating traditional millinery techniques that date back centuries, Jenny has become known for her unique style of sculpted hats that are created on her braid machine from the 1800’s. Jenny’s previous clients include Oprah Winfrey, Madonna, Michelle Obama, Barbara Corcoran, Nicki Sixx and Neil Diamond. She is looking forward to collaborating with you on a one of a kind look.

The winning bidder’s party of four will get to experience the 148th Kentucky Derby in a style accessible to very few of the more than 150,000 annual spectators. You’ll spend three nights at the Omni Louisville, just steps away from Main Street and Fourth Street Live. Your spacious King Corner Suite will overlook the city skyline and contain amenities such as a curated bourbon bar.

The key to your unparalleled Derby experience will be access to the Mansion, which eclipsed Millionaires Row as the most coveted spot in Churchill Downs to see and be seen. Even the Louisville elite can’t buy tickets to the Mansion—they need to be invited and make a three-year commitment. Given its secret, high-security location, most visitors to the track don’t even know the facility exists.

As soon as you pull into the Churchill Downs parking lot, 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. No detail is overlooked: the ladies room contains a Chanel counter with artists to refresh your makeup, along with a seamstress for anyone suffering a wardrobe malfunction.

Feel like wandering around the Paddocks and being photographed with your favorite jockey and horse or trying on the Longines diamond watches given to the winning jockey, trainer and owner? Just ask your concierge. There’s even a betting advisor who patrols the Mansion, dispensing inside information. When the bugle sounds, you’ll have an unobstructed view of the race from the balcony or covered terrace.

The festivities officially begin the day before the Derby with the Kentucky Oaks, America’s foremost race for three-year old fillies. The Longines Kentucky Oaks is also one of the oldest American sporting events, having been established along with the Derby in 1875. The race is also known for the Kentucky Oaks Charitable Initiative, which has raised more than $1 million since inception in the battle against breast cancer.

Churchill Downs itself has been designated a National Historic Landmark. It was founded by Colonel Meriweather Lewis Clark, Jr., grandson of the explorer William Clark and hosts live racing beginning one week before the Derby and extending to July 4th. The Derby itself is the first leg of the prestigious Triple Crown, which has been won by 13 horses beginning with Sir Barton in 1919 and most recently Justify in 2018.

It wouldn’t be Kentucky if you weren’t drinking bourbon, and downtown Louisville is dotted with tasting rooms. You’ll experience an exclusive, VIP tasting of rare whiskeys at the Old Carter showroom on West Market Street.

Sherri and Mark Carter are winemakers and distillers who are participating in the 2022 Naples Winter Wine Festival as Meet the Kids Day vintners. A leading critic described their wines as “swoon-inducing,” and their Cabernets have received ten perfect 100-point scores from Jeb Dunnuck, Lisa Perotti-Brown and Robert Parker, Jr.

The Carters founded the Old Carter Whiskey Co. after falling in love with the distilling process. As with their wine, the Carters strive for perfect balance in their barrel-strength whiskeys, showcasing dynamic flavors and full-bodied mouthfeel. After sampling the versatility of their range, you’ll take home a Large Format bottle of Old Carter Whiskey and an original, racing-themed oil painting created by Sherri.

This incomparable Kentucky Derby experience is just one bid away: Raise you paddle and make it yours!

Insider's Info

Roundtrip, Private Air is on a Phenom 300 and originates from Naples, Florida. Roundtrip airport transfer and private ground transportation for the duration of the trip is included. Gratuities are not included. This trip is date specific and must be taken May 5, 2022 – May 8, 2022. Tasting at Old Carter Whiskey to be scheduled for a mutually agreeable time during the dates of the trip. Food and beverages are only included as part of the Mansion tickets. All other food and beverage during the trip is not included and the responsibility of the winning bidder. Two (2) $1,500 gift certificates for custom hats will be provided by Jenny Pfanenstiel of Formé Millinery Co. Any cost above $1,500 per person and cost to ship the hat is the responsibility of the winning bidder. Gift certificates must be redeemed by November 1, 2022.


Carter Cellars, Jenny Pfanenstiel, Featured Milliner of the 148th Kentucky Derby and The Trustees of the Naples Children & Education Foundation
Airfare donated by Libby & Rick Germain

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