2025 Auction Lots

4 – 1.5 Liter 2016 Stonestreet Estate Vineyards Christopher’s Cabernet Sauvignon
4 – 1.5 Liter 2018 Stonestreet Estate Vineyards Upper Barn Chardonnay

Intimate four (4) night Kentucky experience with Stonestreet Farm in October 2025 for four (4) couples

Roundtrip, Private Air from Naples, Florida to Lexington, Kentucky on a Flexjet Challenger 300
Roundtrip, ground transportation to all stated activities

Four (4) nights’ accommodations at two (2) private guest houses on the Stonestreet Farm property in Lexington, Kentucky
One (1) full day at the races with Club Level access at Keeneland Racetrack
Full day private tour of Bourbon Trail distilleries
Dinner at Carson’s on Main
Dinner at Epping’s on Eastside
Dinner at Jeff Ruby’s Steakhouse

Four couples will indulge in the two high points of Kentucky culture: bourbon and horse racing. An exciting look into the glamorous world of raising and training Thoroughbreds will be paired with visits to some of the state’s most famous distilleries.

Many know Barbara Banke and the late Jess Jackson for their renowned American wine estates, but fewer realize their deep ties to horse racing. Jess Stonestreet Jackson’s love for racing began as a boy watching Seabiscuit win the 1938 Bay Meadows Handicap. His success with Kendall-Jackson wines allowed him to pursue Thoroughbred racing. In 2005, he purchased Stonestreet Farm in Kentucky. Jackson later acquired a controlling interest in Curlin, who won the Preakness Stakes and Breeders’ Cup Classic in 2007, and Rachel Alexandra, the 2009 Kentucky Oaks winner, whose legendary streak made history under his leadership.

The winning bidders’ party will stay at two private guesthouses at Stonestreet Farm and explore a natural environment that “lets horses be horses.” The farm has produced the winners of over 225 graded and listed stakes races. Barbara has served as Chairman of the Breeders’ Cup and Steward of The Jockey Club, as well as on the boards of Keeneland and National Museum of Racing and Hall of Fame.

Your group will dine at three of Lexington’s signature restaurants: Carson’s on Main, which combines local Kentucky products with craft breweries and bourbon; Epping’s on Eastside, an inventive, scratch-kitchen restaurant set in an elegantly restored historic building in Lexington’s Warehouse Block; and Jeff Ruby’s Steakhouse, a lively and elegant venue featuring USDA Prime steaks and fresh seafood.

You’ll be able to experience a full day at Keeneland, a unique venue in Thoroughbred history. Since opening in October 1936, Keeneland has combined world-class racing and industry-leading thoroughbred auctions. During its spring and fall meetings, owners, trainers, riders and fans travel to Lexington to participate. Your group will have privileged access to the Clubhouse, normally restricted to Club members. From there, you’ll enjoy an excellent view of the racecourse and paddock.

No trip to Kentucky is complete without bourbon. Your group will visit top distilleries on the Bourbon Trail, with options including Castle & Key, Bardstown Bourbon Company, Heaven Hill, Maker’s Mark and Woodford Reserve.

Each couple will take home a pair of Magnums representing Stonestreet’s flagship wines. The powerful, Upper Barn Chardonnay, produced from a vineyard planted at 1,800 feet, is a best-in class white wine. Christopher’s Vineyard Cabernet Sauvignon is the estate’s finest mountain-grown Cabernet Sauvignon, concentrated and balanced.

Experience what Kentucky is famous for and help our needy children at the same time: Bid high, bid often and make it your own.

Insider's Info

This lot is for four (4) couples. In order to participate in the Keeneland Racetrack experience, the trip must be taken in October 2025. If winning bidders choose to visit outside of October, the experience at Keeneland Racetrack will not be available. Visit to be scheduled for mutually agreeable dates and based on availability. Private Air must be scheduled at least thirty (30) days in advance and blackout dates in 2025 include but are not limited to January 2-5, 14, 21, 25 and 28; February 1, 4, 8, 11, 13-14, 16-18 and 25; March 1-2, 4, 8-9, 11, 15-16, 18, 22-23, 25 and 29-30; April 1, 5, 7-8, 22, 26 and 29; May 3, 6-7, 10, 13-14, 17, 20, 23-24, 26 and 31; June 3, 7, 9-10, 14, 17-18, 21 and 24-26; July 3-5 and 7; August 29-30; September 1-2; October 10-11 and 14; November 22-27 and 29-30; and December 1-2, 7 and 19-31. Additional blackout dates will be released for the second half of 2025 at a later date. Flexjet requires at least 48-hours notice for any changes to the flight itinerary. Ground transportation is included to all stated activities. Accommodations will be at two (2) of the guest houses on the Stonestreet Farm property. Most guest houses offer three (3) bedrooms with ensuite bathrooms. Two (2) couples will each share a guest house. Dinners listed above are à la carte and served with select wines. Additional meals and beverages are not included. Gratuities are not included for any portion of the trip.

Donor

Barbara Banke, Stonestreet Farm and Stonestreet Winery
Private Air donated by Usha & Monte Ahuja
with special thanks to Flexjet, LLC