You’ve decided to do it. The Kentucky Bourbon Trail is a 95-distillery, award-winning, once-in-a-lifetime road trip through the heartland of American whiskey. Your group is in. The dates are set. And then reality hits.
Where does everyone stay? Who books the distillery tours before they sell out? How do you get 12 people from Louisville to Bardstown and back without anyone ending up behind the wheel after four tastings? What do you do when half the group wants Angel’s Envy and the other half has never heard of Pappy Van Winkle?
Most groups default to two options: a generic Airbnb that wasn’t built for 15 people, or a row of disconnected hotel rooms that kills the group dynamic entirely. Neither offers you the luxury, connection, or curated Experience that a Bourbon Trail trip deserves. There’s a better way.
In this article, you’ll learn:
- Why Louisville is the ultimate base camp for the Kentucky Bourbon Trail, with easy access to 95+ distilleries
- The 4 biggest problems with booking an Airbnb for bourbon trail groups, and what to book instead
- Inside the Swepson Guesthouse, Louisville’s premier group lodging that sleeps up to 42 guests in 10,000 sq ft of historic luxury
- What a truly luxurious bourbon trail experience looks like, private tastings, curated itineraries, group transportation, and a Dedicated Experience Curator
- How to plan the perfect bourbon trail trip in 3 simple steps, from discovery call to arriving with zero stress
- Answers to the most common Bourbon Trail questions, including how many distilleries, where to fly in, what to wear, how long to go, and more
Why Louisville Is the Best Base for the Kentucky Bourbon Trail
Louisville isn’t just on the way to the Bourbon Trail; it is the Bourbon Trail. Named one of the New York Times ‘52 Places to Travel’ and one of Travel + Leisure’s Top 10 Best Food Cities in the U.S., Louisville is a city that punches well above its weight.
From Louisville, your group can reach:
- Heaven Hill, Buffalo Trace, and Maker’s Mark, all within 60–90 minutes south along the Bourbon Trail corridor
- The Urban Bourbon Trail, 25+ bars and restaurants within the city itself, highlighting Louisville’s best bourbon bars and cocktail culture
- Angel’s Envy, Rabbit Hole, and Michter’s Fort Nelson, award-winning urban distilleries, are steps from your front door.
- Churchill Downs, the Muhammad Ali Center, and the Louisville Slugger Museum, for when the group wants a break from bourbon
Louisville’s central location means you can design a 2, 3, or even 5-day bourbon trail itinerary that radiates outward each day and returns to a single, beautiful home base every evening, no packing, no re-checking in, no compromises.
Why an Airbnb Simply Doesn’t Cut It for Bourbon Trail Groups
The Airbnb alternative search is booming, and for good reason. Travelers are starting to realize what seasoned group planners have known all along: most standard Airbnb listings were never designed for the pace, logistics, and shared Experience that a Bourbon Trail trip actually requires.
Here’s what typically goes wrong:
- Space that looks bigger in photos. A 6-bedroom Airbnb sounds spacious until 14 people are sharing two bathrooms before a 9 am distillery tour.
- Zero local expertise. Your Airbnb host is not going to call Woodford Reserve to hold a private tasting for your group of 20. You’re on your own.
- No transportation solution. The #1 logistical challenge on any bourbon tour isn’t the distilleries, it’s getting a group of adults there and back safely. An Airbnb offers exactly zero help here.
- Cookie-cutter Experience. You came to Kentucky for something unforgettable. A generic rental home in a neighborhood with no walkability delivers the opposite.
The better question isn’t “which Airbnb should we book?” It’s: “Is there a smarter way to do this entirely?” There is.
Plan the Ultimate Bourbon Trail Adventure with Super Stays
Spacious Properties For All Your Group Travel Needs
Where to Stay on the Bourbon Trail: Introducing Super Stays
Super Stays is Louisville’s premier group lodging experience, and the only option in the city that combines luxury accommodation, local expertise, and done-for-you bourbon trail tour packages under one roof.
Think of it as a luxury hotel, vacation rental, and personal travel agent all rolled into one. Not a boring cookie-cutter rental or a big-box hotel chain, Super Stays is a curated collection of historic properties reimagined for how groups actually travel.
The Swepson Guesthouse: Your Bourbon Trail Home Base
Meet the crown jewel of Super Stays: Swepson Guesthouse.
Originally built in 1909, this 10,000-square-foot property has been fully restored with group travel in mind. The historic character is still there. The layout and functionality are built for how people actually travel today. Swepson accommodates up to 42 guests with 22 beds, 15 bedrooms, and 10 bathrooms. There are six separate living areas, giving your group room to spread out, plus three private decks for fresh air and downtime.
The property is designed as five self-contained units that can open up to one another or operate independently. That setup allows for shared meals, late-night conversations, and a central gathering space, while still giving guests privacy when they need it. Nestled in the lively Germantown neighborhood of Louisville, you’re just a stroll away from delightful coffee shops, bars, and restaurants.
From the moment you receive your private keycode and step through the secure courtyard, the Swepson feels less like a rental and more like a luxury retreat built specifically for your group.
What a Luxury Bourbon Trail Experience Actually Looks Like
This is where Super Stays separates itself from every other bourbon trail lodging option in Kentucky. Staying here isn’t just about the beds, it’s about everything that comes with them.
Your Dedicated Experience Curator handles;
- Experience exclusive bourbon tastings at top distilleries, customized to suit your group’s preferences! Enjoy a carefully curated itinerary that includes both famous names like Woodford Reserve and hidden gems.
- With group transportation provided, everyone can relax after a day of tastings. Savor memorable dining experiences with private chef dinners on Louisville’s Restaurant Row.
- Additionally, our arrival logistics, featuring a stocked fridge and morning pastries, ensure a seamless and special check-in for your group.
Whether you’re planning a bachelor party on the Bourbon Trail, a corporate incentive trip, a milestone birthday, or a friends’ getaway, your Experience Curator makes sure the logistics are invisible, and the memories are not.
What Guests Say About Staying With Super Stays
“Super Stays was a joy to work with. They helped assemble an excellent bourbon-tasting itinerary, including transportation and our choice of distilleries. The logistics were 100% in place when we got there, and the whole day went super smoothly.”, Andrea, Louisville, KY (Husband’s 50th Birthday Group)
“The details and the extra mile from Super Stays made our weekend a success! We rented the Guesthouse for Derby Weekend, and I would rent it again in a heartbeat. I have only amazing things to say about Super Stays, they were the best!”, Crystal, Corporate Derby Weekend Group (40 Guests)
How to Plan the Perfect Bourbon Trail Trip With Super Stays
Planning your bourbon trail vacation with Super Stays follows three simple steps:
- Book a free discovery call. Your Dedicated Experience Curator learns about your group size, dates, interests, must-visit distilleries, and budget: zero pressure, zero commitment.
- Receive your custom itinerary. Super Stays builds a fully personalized bourbon trail tour package, including lodging, distillery reservations, transportation, and dining, all lined up and confirmed.
- Show up and enjoy. Your only job is to arrive, taste outstanding bourbon, and let your group think you’re the best trip planner they’ve ever met.
Frequently Asked Questions About the Kentucky Bourbon Trail
What is the Kentucky Bourbon Trail?
The Kentucky Bourbon Trail is an official tourism program created by the Kentucky Distillers’ Association that connects 95+ distilleries across the state into a world-class whiskey travel experience. Kentucky is responsible for approximately 95% of the world’s bourbon supply, and the bourbon trail celebrates this heritage by inviting visitors to explore distilleries, barrelhouses, and tasting rooms that bring bourbon to life. From well-known brands like Maker’s Mark and Buffalo Trace to small-batch craft operations, the trail offers a variety of experiences to suit every palate, with Louisville located at its heart.
Where is the Bourbon Trail located in Kentucky?
The Bourbon Trail beautifully weaves through central and northern Kentucky, showcasing incredible distillery hubs in Louisville, Bardstown—proudly known as the “Bourbon Capital of the World”—Lawrenceburg, Versailles, and Loretto. Louisville makes for the perfect starting point, brimming with a vibrant urban distillery scene and providing easy access to explore every exciting part of the trail. Discover the rich flavors and history waiting for you! From the Swepson Guesthouse in Louisville’s Germantown neighborhood, you can reach Bardstown in under an hour and Maker’s Mark in roughly 75 minutes.
How many distilleries are on the Bourbon Trail?
There are 95+ distilleries on the Kentucky Bourbon Trail, spread across the Kentucky Bourbon Trail and the Kentucky Bourbon Trail Craft Tour (which highlights smaller, artisan producers). You won’t do them all in one trip, nor should you try. Super Stays’ Experience Curators help groups identify the right 5–8 distilleries based on their interests, whether that’s the classic heritage giants, hidden craft gems, or a mix of both.
How long does it take to do the Bourbon Trail?
Most groups plan 2–5 days for a meaningful Bourbon Trail experience. A 3-day itinerary is the sweet spot, enough time to visit 5–7 distilleries, explore Louisville’s Urban Bourbon Trail, enjoy a private group tasting, and still have evenings free for dining and exploring the city. Super Stays offers a complimentary 3-Day Louisville Guide that maps out exactly this kind of itinerary for your group.
Where should I fly into for the Bourbon Trail?
Arrive at Louisville Muhammad Ali International Airport (SDF) for an unforgettable Bourbon Trail experience! With multiple major airlines serving the airport, you are only 20 minutes away from downtown Louisville. If you enjoy scenic drives, consider flying into Cincinnati (CVG) or Nashville (BNA), both just a beautiful 2 to 3 hours away by car. Enjoy your adventure! Once you land in Louisville, Super Stays can arrange group transportation directly from the airport to the Swepson Guesthouse, no rental cars required.
What should I wear on the Bourbon Trail?
Dress smart casual with comfortable, closed-toe shoes. Many distilleries involve walking across gravel paths, rickhouses (barrel warehouses), and uneven outdoor terrain, heels and flip-flops are not your friends. Layers are a good idea, since barrel warehouses can be cool even in summer, for private tastings arranged through Super Stays, smart casual attire fits perfectly. If your group is celebrating a special occasion, feel free to dress it up; the distilleries can accommodate.
How much does a Bourbon Trail trip cost?
The cost of a Bourbon Trail trip varies widely based on group size, duration, and the level of Experience you want. At individual distilleries, tasting fees usually range from $20 to $75+ per person. For a seamless experience, consider Super Stays’ bourbon trail tour packages, which combine lodging, transportation, and curated adventures into a single, clear price so that you can enjoy every moment without budget surprises! For groups of 10 or more, this approach is almost always more cost-effective per person than booking each element separately. Contact your Dedicated Experience Curator for a custom quote based on your group’s size and dates.
Can you do the Bourbon Trail with a large group?
Absolutely, and Super Stays specializes in Bourbon Trail experiences for groups of 10 to 40+ people. Large groups actually benefit most from the concierge model; coordinating transportation, reservations, and lodging for 20 or 30 people on your own is a logistical nightmare. Super Stays handles every detail, from securing private tasting rooms that accommodate your entire group to arranging chartered transportation so no one has to be the designated driver.
The Bottom Line on Where to Stay on the Bourbon Trail
The Kentucky Bourbon Trail is one of the great American travel experiences. It deserves more than a random Airbnb booking and a wing-and-a-prayer itinerary. When your group chooses Super Stays, you’re not just choosing a place to sleep; you’re choosing a curated, luxury bourbon experience where every detail is taken care of, every tasting is reserved, and every guest leaves with stories they’ll tell for years.
That’s the Super Stays difference. That’s what it means to stay on the Bourbon Trail truly.
Ready to Plan Your Bourbon Trail Trip?
Super Stays has limited availability for group bookings. Spots fill quickly around Kentucky Derby Weekend, holidays, and peak bourbon season (September–November). The earlier you reach out, the better your options.
Your Dedicated Experience Curator is ready to build the perfect itinerary, from luxury bourbon trail lodging and private tastings to transportation and dining. All you have to do is reach out.
Schedule Your Free Planning Call:
📞 Phone: (502) 208-8915
📥 Free 3-Day Louisville Guide:
✉️ Email: frontdesk@superstaysstr.com
Limited 2026 availability. Contact us today to secure your preferred dates.
Plan the Ultimate Bourbon Trail Adventure with Super Stays
Spacious Properties For All Your Group Travel Needs
