Kentucky Bourbon Trail with It's Bourbon Night

Dates

Oct 18–23, 2023

Group Size

10–23 Travelers

Duration

6 days, 5 nights

Activity Level

Relaxation

About This Trip

Home to the annual horse derby and the largest cave system in the world, Kentucky is perhaps still best known for its distinct, delicious export of bourbon and rye whisky. With 95% of bourbon distilled in the state, the classic "Bourbon Trail" is a must-visit, for everyone from the armchair alcohol enthusiast to the whiskey connoisseur. On this six-day trip you'll soak in the atmosphere and sights, and plenty of booze, as you drink your way from distillery to distillery, learn about the history and production techniques, and purchase plenty of bottles to bring home.
$2,750USD
$2,850USD
Oct 18–23, 2023
6 days
Trip Closed

Meet Your Host

It's Bourbon Night
It's Bourbon Night

It's Bourbon Night is a YouTube channel co-hosted by two Kentuckians, Chad Perkins and Sara Ahlgrim, focused primarily on reviewing and discussing all things Bourbon and American Whiskey. With over 500 unique episodes, their show explores travel and lifestyle coverage, blind flights, individual bottle reviews, and weekly interactive live streams.

View Full Profile

Trip Activities

  • Stroll on Whiskey Row

  • Craft Your Own Old Fashioned Experience

  • Louisville Distillery Visits

  • Barn8 at Hermitage Group Dinner

  • Bourbon Blind Tasting 101

  • Bardstown Distillery Visits

  • Kentucky Cooperage Tour

  • Castle and Key Distillery Visit

  • Lexington Distillery District Visit

Included in Your Trip

  • Double occupancy in 3-star hotels

  • Local Guide throughout trip

  • All city transfers

  • Arrival airport transfer (2 pm on first day)

  • Departure airport transfer (morning of the last day)

Not Included

  • International flights

  • Food and alcohol (except as noted)

  • Visas and travel insurance

  • Airport transfers outside of designated times

  • Tips for Guides

Itinerary

*All durations are approximate

Day 1

Info

Welcome to Kentucky! Take your transfer into Louisville and meet the rest of your group at a welcome dinner to get to know each other and cheers to the week ahead!

Airport Transfer

30 Mins

TrovaTrip will provide one transfer from Louisville Muhammad Ali International Airport (SDF) at 2 pm.

dinner

Get to know your group at the welcome dinner.

Stroll on Whiskey Row

1 Hour

After dinner, head out to Whiskey Row for a stroll down the famous street, stopping to try bourbon and rye at some of the bars along the way.

Seelbach Hilton Louisville (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 1/2

Overnight in Louisville

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Day 2

Info

Today you'll visit the Frazier History Museum on the banks of the Ohio River where you'll learn how to craft your own old-fashioned, as part of a cocktail-making class. Later, you'll take in a few unique distilleries, then explore on your own before traveling into the countryside to enjoy a group dinner at Barn8.

breakfast

Breakfast at the hotel is included.

Craft Your Own Old Fashioned Experience

2 Hours

You’ll learn how to make the official cocktail of Louisville. Instructed by certified bourbon stewards, who will take you through the process of making a traditional old fashioned, with your own unique twist, while at the same time, providing some fascinating history about the cocktail.

Louisville Distillery Visits

2 Hours 30 Mins

After your cocktail experience, join the group for a few distillery visits. The distilleries will vary by day of the week and group interest, but may include Kentucky Peerless, Copper and Kings or Rabbit Hole.

Barn8 at Hermitage Group Dinner

2 Hours 30 Mins

Located on the grounds of the historic Hermitage Farm, enjoy an included meal and on your account try some exceptional small-batch selections and an assortment of unique craft distillations.

dinner

Dinner at Barn8 is included.

Seelbach Hilton Louisville (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 2/2

Overnight in Louisville

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Day 3

Info

From Louisville, you’ll head southeast to Bardstown, home to many smaller distilleries. Your visit will include a blind tasting 101 experience at the Bardstown Bourbon Company and later you’ll get to explore some of the local distilleries.

breakfast

Breakfast at the hotel is included.

Louisville to Bardstown

1 Hour

Bourbon Blind Tasting 101

1 Hour

Tips, tricks, and a good time! From grain to glass, this class will teach how to identify the key characteristics of aroma, palate, and finish. Learn the nuances of grains, aging, and proof then apply your skills to your next tasting exercise. Filled with immersive flavor exercises, this class is not to be missed on your bourbon trail adventure.

Bardstown Distillery Visits

2 Hours 30 Mins

After the blind tasting experience, join your group for some local distillery visits. Access to the distilleries will vary depending on the day of the week and group interest, but may include Four Roses Cox Creek, Maker's Mark or Old Steelhouse Distillery.

Hampton Inn Bardstown (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 1/2

Overnight in Bardstown

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Day 4

Info

Today is about cooperage, the making of barrels and casks. You'll drive to the town of Lebanon and see first-hand how the barrels that store the bourbon are made. Later, enjoy some free time to explore more of Bardstown.

breakfast

Breakfast at the hotel is included.

Kentucky Cooperage Tour

45 Mins

Learn about the ancient art of barrel making from the experts who will demonstrate the process of bending, charring, sealing and aging. You’ll see the physical labor that goes into creating the barrels for some of Kentucky’s best bourbon distilleries.

Hampton Inn Bardstown (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 2/2

Overnight in Bardstown

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Day 5

Info

On your final full day in Kentucky, you'll visit the town of Frankfort and the Castle and Key Distillery. You’ll continue on to Lexington and the Distillery District, as well as the two working bourbon distilleries on the historic site, which serve as an anchor for the up-and-coming neighborhood. This easily walkable area combined with its diverse food and drink offerings makes the Distillery District one of Lexington’s most exciting hotspots.

breakfast

Breakfast at the hotel is included.

Transfer to Frankfort

1 Hour

Castle and Key Distillery Visit

1 Hour 30 Mins

Reimagined in 2014 in the ruins of a historic distillery, dating back to 1887, Castle and Key produce top quality spirits the traditional Kentucky way. On your visit, you'll view the distillation equipment, hear the Castle's story first-hand, enjoy the sunken gardens, and most importantly get a taste of their spirits.

Transfer to Lexington

45 Mins

Lexington Distillery District Visit

2 Hours 30 Mins

On arrival to Lexington, join the group for a few distillery visits. The distilleries will vary by day of the week and group interest but may include James E. Pepper, W.M. Tarr, or Barrel House Distillers.

dinner

Farewell dinner is included.

The Campbell House Lexington (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 1/1

Overnight in Lexington

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Day 6

Info

All good things must come to an end! You'll transfer to the airport and bid farewell for now.

breakfast

Breakfast at the hotel is included.

Airport Transfer

1 Hour 30 Mins

TrovaTrip will provide one transfer to Louisville Muhammad Ali International Airport (SDF) on the last day.

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Physical Activity Level:Relaxation

These trips are designed to help you get into (and stay in) chill mode. Think hanging out, good food and good conversation. These trips won't make you break a sweat unless you want to.

Cancellation Policy

We get it—life happens. Here's how cancellations work depending on where you're at in the process:

Spot Pending

100% refundable
Not confirmed yet? No worries. You can cancel at any time for a full refund.

Spot Confirmed With 91 or More Days Before Your Trip

Partially refundable + credit towards a future trip
You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment.

Spot Confirmed With 90 or Fewer Days Before Your Trip

Non-refundable
At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.

HIGHLY RECOMMENDED: Protect Your Adventure-Invest in Peace of Mind

We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events—from illness to emergencies—that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.

After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.

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FAQ

Traveling with TrovaTrip

What's it like to travel on a Trova Trip?

Trova Trips are curated group travel experiences designed to help you see the world, meet new people, and connect over shared interests. Each trip is hosted by a community leader you know and trust, and run by professional local Operators who handle the logistics. Expect meaningful experiences, authentic activities, and a like-minded group to share it all with.

What's the difference between the Host, the Operator, and Trova?

Great question! Each plays a key role in bringing your experience to life:

  • The Host is your community leader who brings the group together, fosters connection, and perhaps leads a workshop or two. They're there to bring the vibes, not the logistics. That's the Tour Operator's job.
  • The Operator is the professional travel company that runs the trip on the ground. They handle it all—accommodations, local Guides, activities, and safety. Every Operator we partner with is licensed, insured, and vetted to deliver high-quality group travel.
  • TrovaTrip is the platform who connects it all. We help design the trips, partner with Hosts with Operators, and support you before and during your journey to ensure everything runs smoothly.

In short: The Host brings the vibe, the Operator runs the trip, and we make it all happen. Read more about who does what here.

I'm nervous to book. How can I feel more confident?

First, let us say—it's totally understandable, and you're not alone! Travel can feel intimidating, but we built Trova to take the guesswork out of group travel and earn your trust every step of the way:

    • Every trip is run by licensed Tour Operators with vetted local Guides.
    • Hosts are there to foster connection, meaning you'll arrive solo but never feel alone.
    • Itineraries are clearly outlined so you know what to expect, including activity level, example accommodations, and what's included.
    • Our team is available to support you pre-departure, and Operators—plus your local Guide—are on the ground to assist during the trip. And rest assured, all our Operating partners are trained in crisis management.
    • We always recommend travel insurance for extra peace of mind, whether you're traveling with Trova or solo. It can cover medical issues, lost luggage, or even cancellations.

We know it takes trust to book a trip with new people, and we're here to make sure you feel ready, supported, and excited!”

Can I book solo?

Absolutely! As of 2025, almost 84% of TrovaTrip Travelers go solo. (And yes, we may be a little biased, but we think group travel is one of the best ways to meet new people!) You'll have your own bed and the option to book a private room on most trips. Plus you'll be traveling with others who are just as excited to explore and connect.

What if I need to cancel?

We understand that life happens. Our cancellation policy is designed to provide flexibility while balancing the logistics of group travel:

  • Spot pending100% refundable. Not confirmed yet? No worries. You can cancel at any time for a full refund.
  • Spot confirmed with 91 or more days before your tripPartially refundable + credit towards a future trip. You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment. 
  • Spot confirmed with 90 days or fewer before your tripNon-refundable. At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.

HIGHLY RECOMMENDED: Protect Your Adventure–Invest in Peace of Mind
We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events–from illness to emergencies–that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.

After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.

What's included in the trip cost?

Most trips include accommodations, daily activities, ground transportation, some meals, and a dedicated local Guide. Because Travelers are coming from all around the world, flights to and from your destination are not included. Each trip page breaks it all down for you.

Will I have free time?

Yes! While we pack in incredible experiences, most itineraries include built-in free time so you can relax, wander, or check out personal must-sees.

What do the activity levels mean?

Every trip has a physical Activity Level from 1 to 5 so you can find the right fit for your travel style:

  • Level 1 – Relax + Unwind: Minimal movement (spa days, beach lounging, local markets)
  • Level 2 – Low-Key Movement: Light, easy-paced activity (snorkeling, boat tours, gentle hikes)
  • Level 3 – Moderate Activity: Ready to move (multi-day hikes, skiing, camping)
  • Level 4 – Get Your Heart Rate Up: More intense movement (long hikes, biking, active days)
  • Level 5 – Extreme Adventure: High-adrenaline travel (challenging hikes, dives, technical climbs – experience may be required)

You'll find the Activity Level clearly listed on each trip page, and a more in-depth explanation of each level here.

Who can I contact with more questions?

Our support team is here to help! Visit trovatrip.com/company/contact-us to reach out. You can expect to hear back within 2 business days, but probably sooner—our Trova elves are pretty speedy!

Accommodations

What does "or similar" mean next to the accommodations?

When we say “or similar,” it means the hotel listed is an example of what you can expect—not always the exact spot you'll be staying. Sometimes Operators adjust accommodations due to seasonal availability or group size. But rest assured: the quality and comfort will match what's shown.

Why would the accommodations change from time of booking?

Flexibility allows Operators to choose the best-fit accommodations closer to your trip—based on availability, logistics, and what works best for the group (like the number of Travelers and room configurations). This ensures a smooth experience without sacrificing comfort or quality.

Finalized hotel info is typically shared about 30 days before departure in your Traveler Portal, along with your final itinerary.

Trip Operations & Compliance

Who actually runs my trip, and how does Trova keep things safe?

Your trip is operated by licensed, certified Tour Operators who manage all trip logistics and safety—from accommodations and local Guides and day-to-day logistics. All trips comply with local legal and regulatory standards. We vet each Operating partner carefully so you can travel with confidence.

Who do I talk to if I have questions about safety or compliance?

If you have any questions about safety protocols or trip compliance, reach out to us at safety@trovatrip.com. We're here to help.

General Travel Questions

Do I need any documentation to travel?

It depends on where you're headed. Though it is not a universal requirement, many countries require that your passport be valid for at least six months beyond your arrival date. This ensures Travelers have sufficient time to return home even if their visas are extended or if unexpected circumstances arise. 

Some destinations may also require a visa. Check our visa page to consult your country's travel resources.

Do I need any vaccines?

It's always best to check with your healthcare provider or a travel doctor before your trip. You can also visit the CDC website (or your local government's travel health resource) for destination-specific vaccine guidance. Health and safety first!

Are flights included in the trip cost?

Because our Hosts and Travelers are coming from all around the world, flights to and from your destination are not included. Some trips include internal flights (like a short domestic hop), and those details will always be listed on the trip page if applicable.

Can you accommodate my dietary needs?

We’ll do our very best! Our Operators aim to accommodate dietary restrictions, though availability varies by destination. For example, some places offer plenty of vegan and vegetarian choices, while others might be quite limited. The earlier you let us know—through your trip form or by contacting our support team—the better we can prepare. Once you arrive, be sure to remind your local Guide about any allergies or restrictions so they can help you enjoy your meals safely and comfortably.