The Kentucky Bourbon Trail isn’t just a string of distillery tours—it’s an experience you feel in your bones. It’s the clink of glasses after a long day, the off-the-map detours that turn into the highlight reel, and the inside jokes that start somewhere between your second tasting and a scenic drive.
Celebrating 25 years in 2025, the Bourbon Trail now spans 60 distilleries across 27 counties—what started as a simple tasting route is now a rite of passage. And where you stay? That decision shapes everything. It’s not just a place to sleep—it’s home base for the stories you’ll be telling long after the bottles are empty.
Luxury Lodging, Zero Planning Headaches
That’s where Super Stays comes in. Headquartered in Louisville, Super Stays blends the best of hotel convenience, vacation rental flexibility, and concierge-style trip planning. For anyone organizing a bachelor party, corporate retreat, family reunion, or bourbon-fueled birthday bash, this isn’t just a place to stay—it’s your personal headquarters for all things bourbon.
Swepson Guesthouse: Group Travel Game-Changer
The Swepson Guesthouse sits in Louisville’s Germantown neighborhood and stands as the flagship property of Super Stays. Built in 1909, it’s been carefully restored and adapted to host up to 42 guests. Inside, you’ll find 15 bedrooms and 10 bathrooms arranged across five separate suites.
Each suite has its own kitchen, living area, and entrance—ideal for groups who want both privacy and room to gather under one roof.
- 6+ spacious living areas
- 3 outdoor decks
- A private courtyard
- Fully stocked kitchens
- Smart entry and entertainment systems
From high-speed Wi-Fi to beautifully designed common areas, this space is designed for connection. As one guest shared:
“We had 38 people for a company retreat, and not once did it feel cramped. It felt like our own private resort. The bourbon tasting with the private guide was a huge hit!” — Jessica M., corporate guest, April 2024
Custom Bourbon Trail Experiences: The Super Stays Way
With Super Stays, you don’t just book a bed. You book an entire experience—crafted by our Dedicated Experience Curators who know the ins and outs of the trail like true insiders.
Some guest-favorite options include:
- Private guided bourbon tastings at your rental
- VIP access to top distilleries
- Behind-the-scenes tours of new spots like Wenzel Whiskey
- Exclusive barrel blending workshops
- Snack-loaded private buses with music, mood lighting, and plenty of bourbon-safe storage
“The itinerary they built for us included Maker’s Mark, a horse farm tour, and a private chef dinner with bourbon pairings. It was unreal. Felt like a once-in-a-lifetime trip.” — Tim K., bachelor party guest, October 2023
Beyond the Bourbon: Full-Spectrum Itineraries
Sure, bourbon’s the headliner, but there’s so much more to explore:
- Horse Country Tours — Meet retired Kentucky Derby winners
- Louisville Slugger Museum — Swing a bat used by a Hall of Famer
- Glass-Blowing Classes — Make your own souvenir
- The Urban Bourbon Trail — Cocktail crawl with a local guide
And don’t sleep on Super Stays‘ food scene recommendations. From hot chicken joints to James Beard-nominated chefs, Louisville is a sleeper culinary capital.
Planning Pro Tips: Lock in Early
Bourbon experiences book fast—especially during peak season (April to October). Distillery tours, festival tickets, and transportation slots often sell out 30–90 days in advance.
To help, Super Stays offers:
- Free planning calls
- 3-Day Sample Itineraries
- Flexible trip customization tools
Featured Bourbon Trail Hubs
Louisville: Your urban trail gateway. Walk to Old Forester, Angel’s Envy, and Evan Williams. Swepson puts you in striking distance of nightlife, dining, and downtown charm.
Bardstown: Known as the “Bourbon Capital of the World,” it’s home to Willett, Heaven Hill, and more. Super Stays can arrange transportation and dining.
Rising Stars: Keep your eye on Wenzel Whiskey and Southern Kentucky Distillery, up-and-comers with exclusive tasting programs and Instagrammable lounges.
Built for Every Group Type
Extensive Group Perks at Swepson:
- Room for 42
- Interactive bourbon workshops onsite
- Group cocktail classes
- Seamless check-in/check-out process
Private/VIP Experiences for Smaller Groups:
- One-on-one guide-to-guest ratio
- Romantic bourbon dinners with private chefs
- Horseback trail rides + tastings
“I didn’t lift a finger. I just showed up, and it was all there—transportation, tastings, even a surprise cake for my mom’s 60th. It was like having a team of travel elves.” — Lauren B., family celebration, July 2024
Why Super Stays > Hotels and Airbnbs
Local Gems, Unlocked
Super Stays guests get exclusive access to hard-to-book experiences like:
- Churchill Downs VIP seating
- Private Urban Bourbon Trail guides
- Hidden bourbon speakeasies
- Derby Pie baking classes
Every stay comes with a digital guest guide packed with recommendations vetted by locals.
Book Early, Book Smart
The 2025 Kentucky Bourbon Festival is already generating buzz. If you want to attend with a group, now’s the time to start planning.
How to Begin:
- Book a free planning call: superstaysstr.com/book-a-planning-call
- Download the 3-day bourbon trail itinerary
- Ask about bundled deals for Derby Weekend, corporate retreats, and milestone birthdays
FAQ: Kentucky Bourbon Trail Stays with Super Stays
Q1: How early should I book for Bourbon Trail events?
A: Ideally, 60–90 days out, especially for peak season and special events like the Bourbon Festival or Derby Weekend.
Q2: Can Super Stays help me book tours and transportation?
A: Absolutely. It’s all part of the Invisible Concierge experience—we handle logistics from start to finish.
Q3: Are your properties suitable for families or just adult groups?
A: Both! While bourbon is the focus, plenty of family-friendly experiences, such as museums and horse farms, can be added.
Q4: What if we want to visit distilleries outside Louisville?
A: Super Stays can arrange group transportation and overnight accommodations near other trail hotspots like Bardstown.
Q5: Do you offer any packages for special occasions?
A: Yes. We create personalized celebration experiences, including birthdays, anniversaries, bachelor/bachelorette weekends, and more—often with a bourbon twist.
Your Bourbon Trail Legend Starts Here
Whether it’s your first time on the trail or your fifth, Super Stays delivers a level of ease, style, and experience that raises the bar. It’s time to stop settling for “good enough” lodging and step into a fully curated getaway that leaves your group raving.
Let’s make your bourbon trail story one for the books. Cheers!
Plan Your Trip Book your complimentary planning call today at superstaysstr.com, or dial (502) 208-8915 to speak directly with our team.
Everyone Under One Roof
Spacious Properties For Those Bourbon Trail Adventures
