“Too much of anything is bad, but too much good Bourbon whiskey is barely enough.” ― Mark Twain

It has been said Kentucky is the true gateway to America’s iconic deep south. If it truly is (and many people all over the south attest to this), then it is quite possibly where southern hospitality was born.

Your Taste Vacations Kentucky Bourbon Tour emphasizes enjoyment of elite Bourbons, private visits to the Kentucky Bourbon Trail’s most distinguished distilleries, dining at fantastic local restaurants, education about Bourbon from barrel making to the creation of alembic-style stills, and many one-of-a-kind experiences you’ll only find on this vacation. We know you will savor many lasting memories during your time in Kentucky. However, we think your most lasting memory will be the warm and friendly hospitality you will experience from the gracious people of Kentucky.

Tour Highlights

  • Create your own private group
  • Quintessential southern hospitality with stays in either the historic Seelbach hotel or luxurious 21C Museum Hotel
  • Designing your own Kentucky Derby hat, having it expertly made for you, and then wearing it to Churchill Downs (Available on Deluxe Private Tour or with additional upgrade)
  • Bourbon 101 lesson with a local bourbon expert
  • Private tours & tastings at the Brown Forman Cooperage, Buffalo Trace Distillery, Maker’s Mark and more!
  • Exquisite dining experiences at Holly Hill Inn, the Bourbon Bistro, and Copper & King’s
  • A cooking demonstration and private luncheon at Chef Josh Moore’s residence and garden

Tour Itinerary

Day 1


In the late afternoon you’ll meet your Taste Vacations host in the hotel lobby who will escort you for the remainder of your Kentucky Bourbon Tour. We will adjourn for a Bourbon 101 lesson with our fun and erudite local Bourbon expert. You’ll learn about the history and the process that goes into making Bourbon plus sample your first Bourbons. You are on the way to becoming a Bourbon expert!

One of America’s most storied and traditional events is the Kentucky Derby and we will visit Churchill Downs later in the week where you will have the opportunity to live a Kentucky Derby-style day. This all begins when you enter a room filled with flowers, colorful fabrics, and dozens and dozens of Kentucky Derby style hats for women (and men too!).
We bring in Louisville‘s finest hat designers to assist you in designing your very own Kentucky Derby-style hat that you’ll wear while attending the races at Churchill Downs later in the week. Mint Juleps, Manhattans and a sampling of Southern-style appetizers will be served during your fitting. What a great start! 

Finally, dinner tonight will be served at Proof on Main Street located at the eclectic 21c Museum Hotel in downtown Louisville. The cuisine is innovative Southern style delicious, and the hotel epitomizes the very best of 21st-century design. 

Day 2

kentuckyday2After breakfast, you’ll begin your day with a tour of the Brown Forman Cooperage to see how Bourbon barrels are crafted from scratch.  This massive cooperage is a must see to fully understand the complexities that go into the making of a bourbon barrel.

After the tour, we’ll head for the Eastern region of the Kentucky Bourbon Trail. The first distillery you’ll visit will be the impressive Buffalo Trace Distillery located in Frankford, KY.  On the spot where the buffalo migration route crossed the Kentucky River, you’ll find Buffalo Trace, which has been making legendary Bourbon whiskey for over 200 years and is the oldest continuously operating distillery in America.

After our private tour and tasting at Buffalo Trace, we will take you to meet the very personable Chef Quita Michel, a James Beard Foundation Award nominee for best chef in the Southeast multiple times, and dine for lunch at her charming restaurant, Holly Hill Inn.

After your leisurely meal, we will return you to your hotel where you’ll have a nice respite before dinner with Jason Braune, the owner of Louisville’s famous Bourbon Bistro. In a private area of the restaurant, Jason will entertain you with his whimsical anecdotes as he demonstrates his hands-on mixology course titled: “How to makes the perfect Manhattan.” Before sitting down to dinner, Jason will take you into his personal bourbon room to see and sample some of the libations from his unique collection of antique bourbon bottles.

Day 3

kentuckyday3We begin our day with a ride to the Southern region of the Kentucky Bourbon Trail and a visit to Chef Josh Moore and his wife Lindsay’s idyllic country home. The Moore’s 2.5 acre garden supplies almost all the fruits and vegetables for his Italian Restaurant, Volare.  During your garden tour you will pick the fruit and vegetables to be used in a cooking demonstration in Josh’s professional kitchen. After the demonstration, we’ll take a short break and have some bourbon cocktails before sitting down to dine. Certainly Taste Vacations would be remiss if we didn’t include a visit to the consummate Jim Beam Distillery! Founded in 1795 and family operated for over seven generations, the company has been making the highest quality Bourbons (all while battling the wilds of Kentucky, the Great Depression, two wars, and a pesky little thing called Prohibition) and we are thrilled to take you on a tour and tasting here today after lunch. We then visit the Heaven Hill Distillery, American’s largest independent, family-owned distillery. With 900,000 barrels of Kentucky whiskey in their aging room, they account for 17% of the world’s supply of what will be Bourbon. Last but certainly not least, we get the world famous Makers Mark Distillery to open up after hours and hold a private tour and tasting just for us. We’ll tour the facility and then try Maker’s Mark-inspired cocktails paired with a sampling of southern style-appetizers. In addition, you will have the opportunity to hand-dip your very own bottle of Maker’s Mark in their signature red wax to take home as a souvenir. Tonight’s dinner is on your own, given the late lunch and Bourbon tastings.  We are happy to make restaurant suggestions at the best Louisville dining establishments if you wish.

Day 4

kentuckyday4 Before we go to Churchill Downs, we thought you might like to see exactly how the magnificent copper stills are made. These splendid stills are made at Vendome Copper & Brass Works.  This iconic company, in business for over 100 years, has been continually owned and operated by the Sherman family for four generations. You’ll observe as you enter the factory that it is a blur of determined men and women who are absolutely hell bent upon making the finest copper stills in the world.  It is quite an interesting and amazing process!

After your tour of the stills concludes we will return you to your hotel to gather your Kentucky Derby hats and get dressed to the 9’s for your day at Churchill Downs.  Taste Vacations has provided you with entrance into Churchill Downs famed members-only Turf Club for lunch. After dinner, you’ll have a birds-eye view of the races as you sit and cheer your horses on to victory in your members-only box seats. We will even provide you with a local handicapper to help you with your bets.

After the last race has been completed, we will return you to the hotel to rest up before tonight’s dinner soiree’. We will head to Volare, the Italian restaurant owned by our now favorite chef Josh Moore, so we can compare lunch at his home with dinner at his restaurant. It always seems so much more special anyways when you know the chef!

Day 5

This morning, you are welcome to rise at any time you wish. Breakfast will be provided for you in our host hotel and you are then free to go on your way, either catching a car to the airport or continuing on your travels with fond memories of Kentucky!

Tour Details

Tour Details

  • Location: Kentucky
  • Next Tour Date: Private Tour Only
  • Trip Price Per Person: $3,995
  • Optional single supplement: $950
  • Host: TBD
  • Meals: All Meals Included (except dinner on Day Three when a late lunch is provided)

Request Info      Book Tour

Private Tour Option

  • Private Tours are available to book with your own group on any date you choose, given lodging availability, as either Classic or Deluxe
  • Classic  Tour: $3,995 per person (optional $950 single suppl.)
  • Minimum: 8 people
  • Customizations to the above itinerary possible with additional per person fees 
Make It Private

As is with every Taste Vacation tour, the attention to detail is incredible. Everything from ensuring that participants have enough wine, tasting spectacular wines, visiting exclusive wineries, dining on great food, touring beautiful vineyards, plenty of activities to keep us busy, and enjoying unique restaurants is covered.

Elizabeth & Jake

I was concerned about the limitations of being on a guided tour as well as having to spend the entire time with a group of strangers. What I found was that the tours were extremely well planned and the accommodations, meals, wine tastings, and activities were perfect! And at the end of the trip, the people that began the tour not knowing each other, parted as a group of forever friends planning another adventure together with Taste Vacations.

Alice T.

Tour Accommodations


Located in the heart of downtown Louisville, the Seelbach Hilton is one of Kentucky’s premiere luxury accommodations. This classic hotel actually inspired F. Scott Fitzgerald enough that he used it as the backdrop for Tom and Daisy Buchanan’s wedding in the Great Gatsby. Arriving at the Seelbach means taking a step back in time – back to the glamor and energy of the 1920’s where music roared and the bourbon flowed. We will partake in all that fun, but will have cozy beds and luxurious linens that wait for us in our private rooms.

Accommodation upgrades available upon request.

Please note: Hotel is subject to availability.  If listed hotel is not available at time of tour, a hotel that is equal or better to the original will be secured.

What is Included

  • All Local Transportation
  • Double Occupancy Lodging
  • All Meals except dinner on Day Three when a late lunch is provided
  • All Scheduled Activities
  • Whiskey During Organized Tastings
  • Beverages Included With Meals on Deluxe Private Tours
  • Professional Local Guide
  • Your Taste Vacations Host (except on smaller private tours of less than 10 people)

Not Included: Travel to and from destination, alcoholic beverages with meals (included on Deluxe Private Tours), personal expenses, and optional gratuities to local staff and your Host. Travel insurance is also not included, though we highly recommend it.  Check out our Travel Insurance page for more information.

While the general trip itinerary will remain the same, the actual restaurants, hotels, and activities listed are subject to modifications. Changes that are out of our control are common — restaurants close or lose their amazing chef, a winery changes their visiting hours, a hotel gets remodeled, etc. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance.

Arrival & Departure

We will meet you at our downtown Louisville hotel in the afternoon of Day One, allowing you to arrive any time that morning. Airport transport is an easy cab rental or private car reservation. The tour ends with breakfast on Day Five and you are free at that time to head to the airport or elsewhere on your onward travels.