Guide to the KY Bourbon Trail: Perfect 3-Day Itinerary

Kentucky Bourbon Trail 3 Day Itinerary

Day 1: Settling in & Relaxing

Depending on where you’re coming from, you might be jet-lagged or need to recharge your battery. If you’re staying with us at Bourbon Barrel Cottages-we’ve got you covered. We have relaxing private hot tubs, covered porches, propane grill, fast Wi-fi, and more. So, if you arrive later in the day, don’t sweat it and take it easy. 

Morning

If you arrive in the morning on day 1, consider recharging with a hot shower, morning massage, or a soak in the hot tub. Yes, you heard that right! We have a private massage therapist who can treat you to a rejuvenating massage.

The mornings are beautiful in Bourbon country and we love starting our days marveling at the beautiful environment surrounding our property.

Afternoon

It’s about mid-day when you get done with your massage and lunch, but what now? If you’re up for it, we can start with a nice distillery tour today. 

We recommend touring the Wild Turkey Distillery or the Four Roses Distillery as they are located nearby and some of the best stops on the trail. You’ll be able to get a first-hand look at their unique history, iconic distilling process, and taste some of the best bourbon-straight from the source.

Depending on which ticket you purchase, they have tours ranging from 30 minutes to an hour and a half.

Most of the distilleries close around 4-6 p.m., so if you’re itching for a nice late afternoon lunch or dinner, we recommend grabbing dinner at one of the local favorites in the area! This space will also serve as an event venue available for corporate retreats and private meetings.

There are also other local options like Ricardo’s Pub & Grill in Versailles or Bluegrass Sabor right here in Lawrenceburg.

There are also other local options like Ricardo’s Pub & Grill or Bluegrass Sabor.

Evening

When you’re finished eating, enjoy a walk around our beautiful grounds, spend time chatting on your covered porch, or head to bed early to get some extra sleep.



Or, jump in your private hot tub again- why not!?

Day 2: Tour the Distilleries

Today is the day to really dive into the local distilleries and see why we’re known as Bourbon Country. Bourbon Barrel Tours offers private transportation and knowledgeable guides to make this the best day ever. 

Morning/Afternoon

You can start your morning on day two with a quick stop at some local Lawrenceburg coffeehouses like Big Jack’s Coffeehouse or The Hype, offering skinny teas, protein shakes and protein donuts. This will give you the energy and fuel you need to make today great. 

Ready to go? Pile in our luxurious Mercedes limo van, accommodating up to 8 passengers, or our 10-passenger Sprinter Van. For even bigger groups, we can accommodate up to 20 comfortably! Either way-you’re riding in style.

Today is really up to you and we love to customize our tours to your group’s preference. One option is to head to some of Kentucky's major cities and spend the day there.

If you want to visit Lexington, KY-we’ve got the scoop! 

Here are some of the best Lexington Distilleries:

• Lexington Brewing & Distilling Co.
• Barrel House Distilling Co.
• Bespoken Spirits
• Fresh Bourbon Distillery

If you’re not heading to Lexington and want to check out some of the most popular distilleries on The Kentucky Bourbon Trail that can be easily arranged! Popular distilleries include Maker’s Mark, and Buffalo Trace, although they are not located near one another.

However, they’re popular for a reason and are some of the most-raved about distilleries in Kentucky for true, authentic bourbon.

If you want to visit any of these, we suggest finding some nearby distilleries you can see before/after to make the most of your time. 

Here are our suggestions:

Maker’s Mark Distillery

• Loretto, KY
• 57 minutes from Lawrenceburg
• Maker’s Mark Website

Nearby:

• Limestone Branch Distillery
• Log Still Distillery
• Bardstown distilleries: Heaven Hill Distillery, Preservation Distillery, or the Bardstown Bourbon Co.

Buffalo Trace 

• Frankfort, KY
• 15 minutes from Lawrenceburg
• Buffalo Trace Website

Nearby:

• Glenn’s Creek Distilling 
• Mattingly
• Castle & Key Distillery (arguably one of the best tours on the trail and highly recommended)
• Wild Turkey Distillery (located in Versailles, approximately 15 minutes from Buffalo Trace)
• Whiskey Thief Distillery
• Bardstown distilleries: Heaven Hill Distillery, Preservation Distillery, or the Bardstown Bourbon Co., Willett Distillery, Lux Row Distillers

While not technically part of The Kentucky Bourbon Trail, visitors can’t help but rave about this distillery. If you’re a fan or even if you’re not, we recommend stopping by and tasting some of their bourbon.

After your tours, head back to the cottages to relax, or explore one of the local Lawrenceburg or Versailles restaurants for lunch or dinner. By Spring 2026, guests staying at the resort will also enjoy access to our private on-site tasting bar and event space.

Nearby: 

• Whiskey Thief Distilling Co.
• Wild Turkey Distillery

Evening

What a day! You’ve successfully toured a whole host of distilleries today and made it through your busiest day. We invite you to unwind with a movie, bonfire, card games, or just relax and enjoy the warm Kentucky air on your covered porch.

Kentucky Bourbon Distillery Comparison: Tours, Cost, Duration, Booking Policy

Same-Day Booking Reality Check (Updated Insight)

Distilleries most likely to allow same-day bookings:

• Wild Turkey (weekday mornings)
• Whiskey Thief
• Glenn’s Creek
• Mattingly

Advance reservations strongly recommended for:

• Maker’s Mark
• Woodford Reserve
• Angel’s Envy

Day 3: Wrapping Things Up

While we can't tell you how to enjoy your last day here as schedules may vary, we know that by this time you might want to do something else—unless you’re a die-hard bourbon fan. If that’s true, we do have some other options to diversify your last day here.

Morning/Afternoon

If your group enjoys more than just bourbon, we offer tours beyond the Bourbon Trail like our tour of local breweries and vineyards. Lover’s Leap Winery and Rising Sons Winery are both down the road from us!

Spending an afternoon touring other artisans makes for a perfect cap to an unforgettable trip. You can also check out other popular attractions like the Louisville Slugger Museum, Mammoth Cave, or the Ark Encounter.

Evening

If you’re still here in the evening and don't need to drive home or catch a flight, we invite you to enjoy a nice dinner, grab a drink at a local bar, or have a night in with your group! Our cottages are pet-friendly so you can also enjoy a walk with your pup around the area.

Tips for Visiting the Kentucky Bourbon Trail



• Plan Ahead – Some distilleries require reservations, especially for specialty tours.
• Drink Responsibly – Designate a driver or book a tour serviceif you plan to taste at multiple locations.
• Dress Comfortably – Tours often include walking and warehouse visits, so wear comfortable shoes.
• Try Local Cuisine – Pair your bourbon experience with Kentucky favorites like hot browns, burgoo, or country ham.