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Save $1,000 per couple | $500 solo

Bourbon. Horses. Kentucky.

7 days

A Week on the Bourbon Trail

Our Distinctive A+R Style

  • From family-run craft distilleries to iconic world-famous makers, our uniquely in-depth tour reveals the full range of Kentucky spirits and traditions.
  • Thrill to Twilight Racing at iconic Churchill Downs followed by dinner overlooking the track.
  • Fine Southern cooking and farm-fresh fare in Louisville and Lexington.
  • From a stud farm to the auction house and even retirement pastures, we give you a rare look into the life of champion Thoroughbreds.
  • Delight in our farewell dinner with the owners of the picturesque Sun Valley Farm.
  • With 6 nights luxury hotel; 14 meals with wine + spirits at lunch and dinner; extensive sightseeing + bourbon tastings; all transfers; all gratuities except for your Trip Leader.

Show all itinerary details

Day
1

On arrival, you’ll be warmly greeted and escorted to The Brown Hotel, a luxury city landmark for nearly a century. This evening’s dinner features The Hot Brown, the culinary legend created here in 1926.  Meals D

Day
2

Following breakfast, this morning’s touring will begin with a special walking tour of Churchill Downs with VIP access to exclusive areas.  We’ll continue on to Butchertown, a charming city district that is one of Louisville’s oldest neighborhoods, tracing its roots to the early 1800’s.  After perusing the local shops of the Butchertown Market, we’ll enjoy fresh, innovative New American fare for lunch at the Butchertown Grocery before a mixology class at Copper & Kings, a craft distillery gaining fame with its fine brandies.  Our day will finish at the Frazier History Museum, an affiliate of the Smithsonian Institution, with the evening free.  Meals B+L

Day
3

Racing at Churchill Downs

Brown Hotel - Louisville, Kentucky

Today begins with a private trolley tour of Old Louisville, famed for the nation’s largest collection of Victorian mansions. Then it’s off to Louisville’s historic Whiskey Row where we’ll have a tour of the Evans Williams Distillery before a visit to the Old Forester Distillery, home of the first bottled bourbon, and a demonstration of how their barrels are as finely handcrafted now as they were in the late 19th Century.

We’ll return to the Brown Hotel to freshen-up before Twilight Racing at iconic Churchill Downs followed by dinner at legendary Matt Winn’s Steakhouse overlooking the track. Meals B+D

Enjoy this morning’s scenic drive into Central Kentucky where our tour and tasting at the renowned Maker’s Mark Distillery ends with dipping your own bottle of bourbon into their signature red wax.  After lunch at the Bottle & Bond Kitchen to enjoy its fine homemade Southern fare, you’ll tour My Old Kentucky Home. Once the centerpiece of a 1,300-acre plantation, this handsome Federal-style mansion is now a renowned house museum filled with antiques, period art and  finely restored architectural details. At the end of your visit, you’ll even learn how to make the perfect Mint Julep. Then explore the history of Kentucky’s Shaker community and sit down to a delightful garden-to-table dinner at Shaker Village. We’ll continue to Lexington and check in to the new Origin Hotel for a 3-night stay.  Meals B+L+D

Day
5

Welcome to Horse Country

Origin Hotel - Lexington, Kentucky

Keeneland is not just a world-class race course, it’s also the world’s leading Thoroughbred auction house. Get an insider’s look into this rarefied world with our private behind-the-scenes tour. At the James E. Pepper Distillery, a National Historic Landmark, learn about their illustrious history going back to the American Revolution. In the afternoon, we’ll take you to Justin’s House of Bourbon, known for its collection of rare and vintage spirits, and then to a family-owned craft distillery where you’ll create your own custom blend of bourbon. This evening’s unique Bourbon Flavor Wheel dinner at the renowned Holly Hill Inn features farm-to-table dishes that have many of the key tasting notes found in Kentucky bourbon. Created by famed chef and Inn-owner Ouita Michel, it’s a unique way to learn about food, flavors and bourbon-pairings.  Meals B+D
 
Note: Please see our sidebar for the October 10, 2021 Keeneland Racing itinerary.

After breakfast, visit the Old Friends Thoroughbred Retirement Farm to meet their dignified residents and to learn about their innovative approach to providing care for Thoroughbreds whose racing days and breeding careers have come to an end. Then savor your lunch at the fine farm-to-table cuisine of Castle Farms before exploring the lavish halls and landscaped grounds of the Kentucky Castle. In the afternoon, you’ll enjoy a private tour at one of Kentucky's renowned Thoroughbred farms. Later enjoy a magical twilight tour of Sun Valley Farm, set on rolling bluegrass pastures with well-tended fences stretching as far as the eye can see. By special arrangement, sit down to dinner with the Farm’s owners, enjoying congenial conversation and a chance to learn more about their Thoroughbred broodmares, responsible for producing more than 200 Stakes winners worldwide.  Meals B+L+D

Day
7

Departure

After breakfast, we’ll take you to the Lexington airport for your homeward flight.  Meals B
 

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A Day at the Races... Churchill Downs or Keeneland

Horse racing enthusiasts will want to travel on one of our special departures to experience some of the best horse-racing in the country! 

Click to View Our Itineraries Below:
September 14, 2021 Churchill Downs Itinerary >>
October 10, 2021 Keeneland Itinerary >>

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DepartureReturnFromAvailabilityDeparture Note
10 October 202116 October 2021$4,999Sold OutKeeneland Racing - View Itinerary >>
AccommodationPriceAvailability
Our Luxury Hotels$4,999Sold Out
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Save $1,000 per couple + $500 solo on all of our Small Group, Small Ship and Private Journeys when you pay-in-full within 7 days of booking and prior to the final payment date listed in our published terms and conditions.