TLDR: Yes, yes you do.
If you’re planning a trip along the iconic Kentucky Bourbon Trail®, one question always comes up: Do I really need to arrange transportation? The short answer? Yes – especially if you plan on enjoying tastings (which, let’s be honest, is the whole point).
We get it – it might seem easy enough to piece together your own transportation. But with long distances between stops, rural backroads, and scheduled tour times to keep in mind, getting around can be trickier than you think.
Let’s talk about your options – and why having a professional tour company (especially one like Kentucky Bourbon Boys) makes your trip easier, safer, and way more fun.
The Challenges of Getting Around Bourbon Country
Bourbon distilleries may be in the same region, but they are NOT right next to each other. Some are 30+ minutes apart, on winding roads with little to no cell service. If you plan to enjoy tastings, you’ll want to plan ahead for safe transportation.
Here’s what you’ll need to consider when choosing how to get around:
Drinking & Safety – Bourbon tastings add up quickly, and even small pours can make driving unsafe. Kentucky has strict DUI laws, and no one wants to be the one to cut their experience short just to drive.
Distances Between Distilleries – Some of the most famous stops are miles apart, on country roads that aren’t always GPS-friendly. If you miss a turn, you could easily end up on the scenic (but very unplanned) route.
Timing Matters – Tours run on tight schedules, and if you show up late, you might miss your tour completely. Having reliable transportation is the difference between a smooth day and a stressful one.
What Are Your Transportation Options?
So, how do people get around the Bourbon Trail? Let’s look at the most common ways:
Driving Yourself – Probably the least practical (and riskiest) option. Between navigating backroads, skipping tastings to stay sober, and the risk of getting lost in no-service areas, it’s not exactly a relaxing way to spend the day.
Rideshares (Uber/Lyft) – Available sometimes, but very unreliable. You’re at the mercy of a driver showing up (if there’s even one nearby), wait times can be long, and surge pricing adds up fast when booking multiple rides. You might find it easy to snag a ride to a distillery, but because many are in the countryside, its often a big struggle to find one willing to come all the way out there to pick you up, potentially leaving you stranded as far as an hour from your lodging!
Having a Friend Drive – A solid option if you have a willing volunteer. But let’s be honest: someone in your group has to miss out on the fun, and that’s never ideal.
Booking a Tour Company (The Best Choice) – With a dedicated driver, a comfortable vehicle, and a team handling all the details, you don’t have to stress about anything. But not all tour companies are created equal…
Why Kentucky Bourbon Boys is Different
A lot of tour companies will get you from point A to point B, but at Kentucky Bourbon Boys, we do so much more than that.
We’re Kentucky Locals – Born and raised here, we know the history, the backroads, and all the hidden gems along the way. You’re not just getting a driver – you’re getting a bourbon-loving local who’s passionate about making your trip unforgettable.
Private & Custom Tours – Unlike other companies with preset routes or public group tours, every KBB tour is private and built around YOUR perfect day. You pick the distilleries, and we handle the rest.
We Take Care of All the Planning – No need to book tastings, worry about tour times, or coordinate logistics. We handle all of that you just show up and enjoy.
Comfort & Convenience – Our vehicles are clean, spacious, and stocked with snacks and water. Because let’s be real – bourbon tasting is a marathon, not a sprint.
Our Guides Are Like Family – Our family owned and operated claim isn’t just for show! We only hire people we personally know and trust – so you’re getting genuine hospitality, not just a driver following a route. Most of our team members are even Executive Bourbon Stewards with the Stave & Thief Society!
Explore the Bourbon Trail the Right Way
No matter how you choose to get around, the most important thing is doing it safely and stress-free. But if you want a trip that’s easy, fun, and perfectly planned, Kentucky Bourbon Boys is the best way to experience the Bourbon Trail.
We’ll handle the details – you handle the bourbon.
