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Kentucky Bourbon Trail

HISTORY & HERITAGE

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

SAVOR

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

EXPERIENCE

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.

Itinerary Highlights

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.

Louisville

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.

Lexington

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.

FAQs

  1. How many people is this itinerary suitable for?

    Our private itineraries are ideal for groups of four or more—you and friends, families, and multi-generational groups. For groups of six or more, an optional Modern Adventure local guide can be arranged.

  2. What makes a MO/AD experience different?

    Our level of curation and care. We handle everything, overseeing your experience from beginning to end, with the highest levels of ownership and responsibility. We also support you each step of the way, with comprehensive trip materials and itineraries, detailed day-by-day options, insider destination info, gear recommendations, and 24/7 dedicated support.

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

    Preferably three to six months in advance. Alaska’s summer season is short, and demand for permits and float planes and accommodations are high. Advance reservations are important to secure the best locations and accommodations possible.

  4. What is typically included?

    We curate your Modern Adventure to ensure the experiences are authentic and immersive, and included in your trip price. This includes all accommodations, most gear (expedition-quality tents, all cooking gear),  local transport and internal flights, airport transfers, local guides and cultural experts, and all meals.

  5. How much will it cost?

    Private Modern Adventures typically cost $750 to $1,500 per person, per day, and vary by time of year, the number of people in your group, and types of activities (private local guides, private transfers) you prefer. 

  6. What's not included?

    MO/AD Private Departures do not include roundtrip airfare to/from your destination, travel insurance, transportation to your trip’s starting point, lodge incidentals (including room service, laundry service and hotel bar tabs), and any activities or meals not included in your confirmed MO/AD itinerary.

  7. What deposits are required?

    After learning more about you, your interests and preferred style of travel, as well as your preferred travel dates, we will present you with a detailed itinerary including activities, internal flights, transport and accommodations. In order to check and confirm availability for your group, there is a $750 non-refundable deposit due. This will be applied to your final trip cost. 

    Your trip is guaranteed—and your dates secured—with a 25% non-refundable deposit. Many of our local partners, including our hotel and resort partners, require advance deposits to secure the best accommodations. The balance of your trip is due 30 days prior to travel.