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16 Day Kentucky Bourbon Trail
Starting on Jun 01, 2026 ending Jun 16, 2026
Please wait...
DAY 1-4
Shepherdsville, KY
WELCOME
Orientation & Get Acquainted Social – meet your Ambassadors and fellow guests
Welcome Dinner at Local Restaurant
Bourbon Social Event – sample different types of bourbon with your new friends!
Private Motorcoach Transportation to Activities
Frazier History Museum – the official starting point of the Kentucky Bourbon Trail, offering engaging exhibits on Kentucky’s heritage & bourbon
Lunch on Whiskey Row – dine in the historic bourbon district that celebrates Kentucky's bourbon heritage
Evan Williams Bourbon Experience – learn about the first distillery on Whiskey Row, tour an operating distillery & taste their signature spirits
Louisville Guided Motorcoach Tour – a private sightseeing tour of the city’s highlights including Churchill Downs, Falls of the Ohio & Fossil Beds, St. James-Belgravia Historic District & Conrad Castle, Muhammed Ali Center
Kentucky Derby Museum – a deep dive into horse racing history, featuring exhibits, memorabilia & immersive experiences celebrating the Derby
Lunch at Churchill Downs
Churchill Downs – enjoy thrilling races at the home of the world-famous Kentucky Derby
Free Day to Explore Bourbon Country
OPITIONAL: Explore Louisville's Urban Bourbon Trail
OPTIONAL: Bernheim Forest Giants
DAY 5-8
Bardstown, KY
DRIVING MILES 27
My Old Kentucky Dinner Train – a unique culinary experience aboard a vintage train, featuring gourmet meals and scenic views
Private Motorcoach Transportation to Activities
Heaven Hill Distillery Tour and Tasting – explore bourbon production, learn about its history & savor exceptional spirits
Lunch at Local Restaurant
Maker’s Mark Distillery Tour and Tasting – a captivating journey through the whiskey-making process, showcasing craftsmanship, history & iconic red wax-dipped bottles
Free Day to Explore Bourbon Country
My Old Kentucky Home Tour and Lunch – a historic mansion built in 1795 and owned by the Rowan family, offers a glimpse into the antebellum South's charm & elegance
My Old Kentucky Home Culinary Biscuit Demonstration – learn how to make the south's iconic beaten biscuits in the beautiful carriage house
My Old Kentucky Home Southern Julep Demonstration – learn what goes into making a proper Kentucky Mint Julep and taste one of your own
DAY 9-11
Frankfort, KY
DRIVING MILES 53
Private Motor Coach Transportation
Buffalo Trace Distillery Tour and Tasting – a bourbon lover's dream, offering insights into the production of world-class bourbon in a historic setting
Campground Cookout – food, fun and friends!
Private Motorcoach Transportation to Activities
Castle & Key Distillery Experience – with a castle standing proud, explore the historic grounds, witness traditional bourbon-making processes & savor tastings of crafted spirits
Lunch at Local Restaurant
Woodford Reserve Distillery Tour – explore the flavor sources from grain to glass, ending with a tasting of award-winning bourbons
Rebecca Ruth Candy Shop – a sweet experience, showcasing handcrafted chocolates, rich history & Kentucky’s famous bourbon balls
Private Motorcoach Transportation to Activities
Four Roses Distillery Tour – get a glimpse into bourbon-making history, showcasing craftsmanship and tasting opportunities in a charming setting
DAY 12-16
Lexington, KY
DRIVING MILES 28
OPTIONAL: Ark Experience
Private Motorcoach Transportation to Activities
Kentucky Horse Park Tour and Lunch – showcases equestrian history with museums, interactive exhibits & retired racing legends
Keeneland Racetrack Tour – a behind-the-scenes look at Thoroughbred horse racing
Bourbon Social Event – sip on bourbon and socialize with friends!
Private Motorcoach Transportation to Activities
Wild Turkey Distillery Tour – learn about the unique production process, visiting the distillery and a historic rickhouse
Lunch at Local Restaurant
James E. Pepper Distillery Tour – explore the distillery museum, tour the working distillery & savor award-winning whiskeys
Private Motorcoach Transportation to Activities
Lexington Brewing & Distilling Co. Tour and Tasting – an award-winning, family-owned brewery and distillery, shaped by a heritage that includes seven generations of Irish distillers
Farewell Dinner at Local Restaurant
Goodbye Continental Breakfast – grab some food and coffee before we part ways