Destination: Kentucky Bourbon Trail
Savor the Spirit: A 4-Day Kentucky Bourbon Trail Itinerary
If there’s a place where sipping whiskey feels like an art form, it’s Kentucky. Home to 95% of the world’s bourbon, the Bluegrass State invites you to slow down, savor the craftsmanship, and explore its rolling countryside. The Kentucky Bourbon Trail isn’t just about tasting—it’s about immersing yourself in history, hospitality, and the heritage of America’s native spirit.
Here’s a 4-day itinerary for a curated, luxurious take on the Bourbon Trail.
Day 1 – Louisville Arrival & Urban Distilleries
Louisville Slugger Museum
Base: Louisville
Check-In: The Brown Hotel — a historic landmark known for Southern elegance and its iconic Hot Brown sandwich.
Morning: Arrive in Louisville, settle in, and take a stroll through Whiskey Row.
Distillery Visit #1: Old Forester Distilling Co. — The only bourbon continuously sold before, during, and after Prohibition. Their tour includes a working cooperage demonstration.
Lunch: Proof on Main — chic, art-filled dining inside the 21c Museum Hotel.
Distillery Visit #2: Rabbit Hole Distillery — A modern take on bourbon-making with striking architecture and rooftop tastings.
Evening: Dinner at Jeff Ruby’s Steakhouse. End with a nightcap at Angel’s Envy Distillery’s bar (even if you toured elsewhere earlier).
Day 2 – Bardstown: Bourbon Capital of the World
Base: Bardstown
Morning Transfer: Private driver from Louisville to Bardstown (about 1 hour).
Distillery Visit #1: Heaven Hill Bourbon Experience — Immersive history and tastings from the largest family-owned distillery in America.
Lunch: The Rickhouse — bourbon flights and hearty Southern fare in a brick-walled cellar.
Distillery Visit #2: Bardstown Bourbon Company — Known for innovation and sleek, modern facilities. Their “Bourbon + Food” experience pairs spirits with gourmet bites.
Stroll: Explore Bardstown’s charming historic district and shops.
Evening: Dinner at The Kitchen Table at Jim Beam for elevated farm-to-table dining.
Day 3 – Lexington & Horse Country
Base: Lexington
Morning Transfer: Bardstown to Lexington (~1 hr 15 min). Scenic drive through rolling horse farms.
Distillery Visit #1: Buffalo Trace — Legendary bourbon heritage and home to favorites like Blanton’s and Pappy Van Winkle. Their Hard Hat Tour is a must for behind-the-scenes access.
Lunch: Holly Hill Inn — refined Southern cuisine in a historic setting.
Distillery Visit #2: Woodford Reserve — Elegant copper pot stills, limestone aging warehouses, and exceptional reserve tastings.
Evening: Dinner at Coles 735 Main. Stay at the 21c Museum Hotel Lexington or the boutique Gratz Park Inn.
Day 4 – Craft Distilleries & Farewell
Base: Lexington (Departure)
Morning: Stop at Wilderness Trail Distillery in Danville — a rising star with unique mash bills and precision fermentation.
Brunch: Doodles — farm-to-table Southern comfort food with a playful vibe.
Final Sip: If time allows, swing by Castle & Key in Frankfort — a stunning restored distillery designed by the same architect as the Kentucky State Capitol.
Departure: Head home with a few bottles (and maybe a bourbon-scented candle) as souvenirs.
Luxury Travel Tips for the Bourbon Trail
Hire a Private Driver: Allows you to enjoy tastings without worry.
Book Tours Early: Many premium tastings and behind-the-scenes tours sell out weeks in advance.
Mix Big Names & Hidden Gems: The magic is in balancing iconic distilleries with small craft producers.
Stay Central: Splitting overnights between Louisville, Bardstown, and Lexington helps minimize drive time.