Kentucky Bourbon Trail


Follow Kentucky’s Bourbon Trail into heart of Americana, taste the finest bourbons with exclusive MO/AD access


Taste the best of everything at industrial-chic eateries, neighborhood kitchens run by celebrity chefs, and at rollickin' honky tonks


The birthplace of American whiskey, a Churchill Downs horse race, VIP tastings at iconic local distillers

Why Kentucky

Every day of this bluegrass immersion is filled with exclusive, VIP access into the heart of America’s best bourbons, from Louisville to Bardstown and Lexington. Savor the Bluegrass State’s best food and drink in an unforgettable setting of brick streets, winding roads, rolling mountains and horse farms. Then it’s right back to more of the very best bourbon—or as George Bernard Shaw called it, “liquid sunshine.”

Moments That Matter

Meet craft distillers and traditional coopers who char oak barrels in historic rickhouses. Go behind the scenes of the most iconic names in American bourbon, and meet the modern up-and-comers who are crafting whiskey for a new generation. There’s plenty of bourbon to taste⁠, of course—along with catching a horse race at Churchill Downs (site of the Kentucky Derby), eating in honky tonks and riverside distilleries-turned-restaurants, where southern staples are deliciously elevated. This is an experience to stimulate all of your senses.

Your Private Experience

Who It’s For

Lovers of food, culture and of course, whiskey. Great for a long weekend or an extended sojourn.

When to Travel

Our favorite time of year is April to October, especially the mild and sunny days in May, early June and September.

Make It Yours

The end-all-be-all of whiskey journeys? More art? More horses? More fine dining? We'll craft a trip that highlights your finest Kentucky dreams.

Day by Day

Explore bourbon’s birthplace—from Louisville to Bardstown and Lexington—with VIP access at craft distillers, the best local foods, and a horse race at the site of the Kentucky Derby.

Day 1

Welcome to Louisville! (And that’s pronounced LOU-uh-vull.) Settle in to your hotel on historic Whiskey Row, then saunter by 18th-century cast iron-facade buildings brimming with distilleries and tasting rooms to sample a few favorites. Dinner is in the historic neighborhood of Old Louisville for elevated Southern cooking delivered in multiple courses and paired with local bourbons, of course.

  • Private airport transfers
  • Whiskey Row tour
  • Dinner & bourbon pairing

Day 2

Hit the Bourbon Trail, starting with a behind-the-scenes look at the Brown-Forman Cooperage, where oak barrels get hand-crafted then charred into perfect bourbon-aging vessels. Afterwards, start your day’s sips at family-run Peerless distillers, which first opened in 1889. Then you’ll see it’s not all whiskey around here: at Copper & Kings, a modern brandy distillery in Louisville’s Butchertown, you’ll get a private tour and sample some craft cocktails as a perfect chaser to lunch. Finish the day at another Louisivlle icon, Churchill Downs—with dinner and drinks while betting on horses at the fabled home of the Kentucky Derby.

  • Private tasting at Peerless
  • Private tasting at Copper & Kings
  • Lunch at famed honky-tonk
  • Dinner and night horse race at Churchill Downs

Day 3

Today you roll past the bluegrass meadows, horse farms and mountains en route to quaint historic Bardstown, dubbed the Bourbon Capital, where you’ll stop at its most famous resident, Maker’s Mark. Walk through the stages of its whiskey, then finish with a tasting and specially prepared lunch. Your next base is Lexington, home to Kentucky University (and more bourbon, don’t worry), where we’ll have time to explore its historic downtown, which is where you’re based. Next, have a private tasting at the city’s favorite craft spirit supplier, Justin’s House of Bourbon, noted for its robust collection of rare, craft varieties not found elsewhere.

  • Maker’s Mark tasting and lunch
  • Private tasting at Justin’s House of Bourbon

Day 4

Start with an insider’s look at a rural distiller in the spring-fed mountains with over 200 years of experience. Visiting Woodford Distillery is like traveling back in time, and you’ll go behind the scenes on a VIP tour. Afterwards, rinse your palates with cold Kentucky Ale from Lexington Brewing and Distillery back in town. Dinner tonight is a real treat: at a historic distillery on the Elkhorn River, refashioned as Middle Fork, one of Lexington’s most accomplished kitchens. It’s an industrial-chic space with a sprawling open kitchen and wood-fired grill. You’re in no rush, so eat Kentucky-style: slow, with plenty of laughter and drinks.

  • VIP tour & private lunch at Woodford Distillery
  • Tasting at Lexington Brewing and Distillery
  • Dinner at Middle Fork

Where We Sleep

A luxurious boutique hotel on Louisville’s Whiskey Row, an art-filled hotel housed in a 19th-century former bank in downtown Lexington. You’ll love these places.


The perfect Louisville set-up, this new luxury hotel ushers in its location—a historic building on the legendary Whiskey Row—indoors. Step into the brand-new space, with its ground floor steakhouse and upstairs whiskey bar that looks out of a movie. Stunning rooms are decked with all modern amenities.


This one-of-a-kind art hotel in downtown Lexington mixes hospitality and cutting-edge art in the glorious, historic Fayette National Bank Building. After unpacking in your modern, high-ceiling room, look over the center’s building through the historic, towering windows, then pop down to browse the hotel’s 7000-square-foot art museum with rotating exhibits.

People Love MO/AD Private Departures

I am truly a tough critic but you planned an exceptionally fun adventure—no constructive criticism necessary.
Avis C.
Our activities were amazing, and the accommodations and food were excellent.
Peter B.
MO/AD was able to arrange special experiences that are impossible as an individual traveler or family. Amazing!
Christine N.


  1. How many people is this itinerary suitable for?

    We can plan a custom, private departure for any group size. Our custom trips are perfect for a couple wishing to travel on their own, a family, or a multi-generational group. If you’re looking to travel on one of our group departures on a private basis, a minimum number of travelers may apply.

  2. Can you curate an itinerary for a larger group?

    Yes, we can craft an unforgettable milestone celebration or company retreat for groups as large as 40 or more.

  3. What makes a MO/AD experience different?

    Our level of curation, care, and in-country connections. We handle everything, overseeing your experience from beginning to end with the highest levels of ownership and responsibility. We support you every step of the way with comprehensive itineraries, detailed day-by-day descriptions, insider destination info, and 24/7 dedicated support.

  4. How far in advance should I plan my trip?

    Preferably six to nine months in advance and earlier for holiday travel. We stay in unique, in-demand boutique and luxury hotels where advance reservations are important to secure the best accommodations possible. We can help with last-minute travel planning, however availability may be limited.

  5. What is typically included?

    We curate your MO/AD Private Departure to ensure the experiences are authentic, immersive, and included in your trip price. Your itinerary typically includes accommodations, airport transfers, private transportation for all day trips and excursions, privately guided tours with local guides, exclusive VIP access and activities, and meals as detailed in your itinerary.

  6. How much will it cost?

    MO/AD Private Departures typically cost $750 to $1,500 per person, per day, and vary by destination, time of year, number of people in your group, and types of activities you prefer.

  7. What's not included?

    MO/AD Private Departures do not include roundtrip airfare to/from your destination, travel insurance, gratuities for local guides, hotel incidentals, and any activities and meals not included in your itinerary.

  8. What deposits are required?

    After learning more about you, your interests, preferred style of travel, dates, and budget, we will present you with initial ideas and examples of what we can plan for you. In order to design a detailed itinerary and check availability, there is a $500 non-refundable planning deposit due. This will be applied to your final trip cost. Once your itinerary is perfect, we require a 25% non-refundable confirmation deposit to start confirming all of your arrangements. Many of our local partners and hotels require additional advance deposits to secure the best accommodations. The balance of your trip cost is due 90 days prior to travel.

  9. Where can I find the complete terms of my booking?

    See our Terms & Conditions for complete details about our policies regarding your MO/AD Private Departure booking.