Planning a Bourbon Trail tour with a group of 15 or more sounds like a dream—until the group chat turns into chaos. From coordinating transportation and tastings to managing differing expectations, organizing a large-group Kentucky Bourbon Trail experience takes more than just booking a few distillery tours. But when it’s done right? It becomes the kind of trip people talk about for years.
In this article, you’ll learn:
- The top mistakes people make when planning large group Bourbon Trail trips
- How to book transportation for 15+ people (and avoid bourbon bus nightmares)
- Why certain distilleries won’t even take large group reservations
- Sample itineraries for a 1-day or 2-day group Bourbon Trail trip
- Honest pricing breakdowns and logistics comparisons
- What Super Stays does differently to make your group trip seamless
Why the Bourbon Trail Is Booming for Groups
With over 2.1 million visits annually and more than 40 distilleries participating, the Kentucky Bourbon Trail is a significant draw for bachelor parties, corporate retreats, milestone birthdays, and reunions. But the experience changes dramatically when your Group hits double digits.
According to data from the Kentucky Distillers’ Association, over 60% of visitors travel in groups of 6 or more.
But once that number jumps to 15+, it introduces a new set of challenges:
- Most distillery tour bookings cap at 12-14 people
- Transportation needs escalate (think sprinter vans or mini-coaches)
- Dining options become more limited without reservations
- Travel time between distilleries stretches with more people to wrangle
Translation: you can’t wing it.
Plan the Ultimate Bourbon Trail Adventure with Super Stays
Spacious Properties For All Your Group Travel Needs
Common Mistakes People Make When Planning a 15+ Person Bourbon Trail Tour
Assuming Uber or Lyft Will Cut It
Once you hit 10 or more guests, relying on ride-sharing is not only unreliable but also dangerous. Many distilleries are in rural areas where service is spotty and wait times are long. And let’s be honest: no one wants to be the designated driver on a bourbon trip.
Booking Too Many Distilleries in One Day
More isn’t better. Large groups take longer to load in/out, settle in at tastings, and reach the next stop. Aim for a max of 3 distilleries per Day, and space them out with food or activity breaks.
Failing to Reserve Tasting Slots in Advance
Popular distilleries like Buffalo Trace, Woodford Reserve, and Angel’s Envy often book out 3+ weeks in advance for groups. And many won’t accept reservations for parties of 14 or mor
That means you either:
- Book multiple smaller groups
- Choose alternative distilleries with better group policies
- Work with a planner who has existing relationships
Thinking Everyone in the Group Wants the Same Thing
Some want to learn the history. Others want to sip. Many distilleries now offer a variety of experiences—cocktail classes, VIP tastings, history tours—so mix it up.
Real Talk: Transportation Options for 15+ Person Bourbon Trail Tours
Here are your most common options (based on Louisville as your base):
Super Stays includes private transportation in its curated group packages, eliminating this headache completely.
The Distillery Booking Dilemma: What They Don’t Advertise
Here’s the truth: not every distillery is equipped for big groups
Pro tip: Blend iconic names with lesser-known gems like Jeptha Creed or Preservation to keep the day interesting.
Sample Itinerary: 1-Day Bourbon Trail with 15 People
Start in Louisville
- 9:00 AM: Group pickup at Swepson Guesthouse
- 10:00 AM: Tasting + tour at Angel’s Envy
- 12:30 PM: Lunch at Bardstown Bourbon Company Bistro
- 2:00 PM: Tour & cocktail class at Maker’s Mark
- 5:00 PM: Return to Louisville
Add-ons:
- Private chef dinner at the Swepson
- Bourbon mixology contest in the outdoor courtyard
Pricing Breakdown: DIY vs Super Stays Package
For 15 People, 1-Day Bourbon Trail Tour
What Super Stays Does Differently
Super Stays isn’t just a place to sleep—it’s a full-service group experience built around:
- Effortless Planning: Free discovery call, dedicated Experience Curator
- Turnkey Transportation: Private vans, mini-coaches, or custom limo experiences
- Private Tastings & Events: Bourbon pairing dinners, in-home cocktail classes, chef-led meals
- Flexible Layouts: The Swepson Guesthouse sleeps up to 42 in 22 beds, with modular layouts
Our guests say it best:
“The logistics were 100% in place when we got there. Super Stays made it so smooth.” – Andrea, 50th birthday guest.
“We needed to sleep 40 people and plan tastings during the Derby. Super Stays made it work.” – Crystal, Corporate Retreat guest.
Bourbon Trail Frequently Asked Questions
What is the best way to book a Bourbon Trail tour for a group of 15 or more?
The most efficient way is to go through a company like Super Stays that offers full-service group travel planning, including transportation, distillery reservations, and lodging. Trying to book each distillery individually for a group this size is time-consuming and often limited by the distilleries’ group-size restrictions.
Can you visit multiple distilleries in one Day with a large group?
Yes, but you should limit your itinerary to no more than three distilleries per Day. Large groups require more time for loading, settling, and transitions, and most distilleries only offer tasting slots at set times. Adding a lunch or activity break also helps balance the Day.
Do all Kentucky distilleries allow extensive group tastings?
Some distilleries just aren’t set up for large groups. Buffalo Trace and Rabbit Hole, for example, limit tastings to 12 people max—no exceptions. If you’ve got more than that, you’ll either have to split into smaller groups or leave those stops off your list. Others, like Maker’s Mark and Bardstown Bourbon Company, are more flexible and can handle bigger crowds, as long as you give them enough notice. Best move? Call ahead, familiarize yourself with their policies, and don’t wait to book.
What kind of transportation is recommended for 15+ people on the Bourbon Trail?
Options include sprinter vans (up to 14), mini-coaches (15–28), or full-size charter buses for 30+. For 15–20 people, a mini-coach is ideal. Avoid ride shares or self-driving due to safety, reliability, and insurance concerns—especially when alcohol is involved.
How much does a Bourbon Trail tour cost for a large group?
DIY costs range from $5,000+ per Day when you factor in transportation, tastings, meals, and lodging. Super Stays’ curated packages start around $3,750, including private transport, bookings, and accommodation, making it a better value and much less stressful.
Final Thoughts: Want to Be the Group Hero?
When you’re planning for 15+ people, you only get one shot at getting it right. A few wrong moves and you’re the one they roast in the group chat. But done right? You’re the hero who pulled off an unforgettable trip.
Let Super Stays handle the heavy lifting so you can focus on the memories, not the logistics.
Ready to Start Planning Your Bourbon Trail Experience?
Book a free planning call or explore our Bourbon Trail Group Packages now.
📞 Call (502) 208-8915
📧 Email: FrontDesk@SuperStaysstr.com
Book your planning call today: https://superstaysstr.com/book-a-planning-call/
Plan the Ultimate Bourbon Trail Adventure with Super Stays
Spacious Properties For All Your Group Travel Needs
