Ultimate 3-day bourbon trail itinerary (from a local!)

With so many bourbon distilleries to see on the Kentucky Bourbon Trail, it’s certainly hard to fit in as many distillery tours and bourbon tastings as you’d like in just a long weekend. In fact, the Kentucky bourbon trail includes 42 distilleries. That’s why I created this 3-day bourbon trail itinerary. It can help maximize your time, save money, visit some of my favorite distilleries, and create a meaningful trip along the way!

How to plan a Bourbon Trail trip

Gone are the days when bourbon lovers could just show up at a distillery and join a tour without reservations. Today planning a trip to the Bourbon Trail requires a lot more time and organization. You must book your tickets in advance to secure a tour, which means you need a solid plan of location, timing between tours, and prioritization on which locations you are most interested in so you don’t miss it.

Most tours open reservations between 2-3 months in advance. Which means you need your itinerary finalized by then, so you know where you want to go, and when. But don’t worry – I’ve helped you plan the ultimate 3-day itinerary to pack it full of unique bourbon trail experiences!

Listen to me share about the Bourbon Trail on Destinations Beyond Expectations.

Getting around the Bourbon Trail

Unless you opt for a guided tour, the best way to get around distilleries outside of the immediate Louisville area is to rent a car. It’s really the only way to see the distilleries if you don’t go with a guided tour. Plus, it offers you flexibility in time between your stops, too.

Tastings on the trail are small amounts of bourbon, with strict regulations on the amount of alcohol you can consume. Distilleries are only allowed to offer you 1 3/4 ounces at a tasting. Still, if you opt to book a rental car for your bourbon trail experience, be sure to select one person as the driver, especially if you plan to enjoy a cocktail at the distillery’s bars.

Pro tip! I book my rental cars with AutoSlash. It’s a free tool that compares all your car rental options to give you the best price.

3-Day Bourbon Trail Itinerary – the ultimate guide!

This 3-day itinerary is designed to be self-guided. With so many great distilleries to choose from, quality eats around the trail, and more, this is the perfect way to visit the bourbon trail and have a well-rounded experience.

Day 1: Arrive in Louisville and enjoy an afternoon tour

There are just a few airports offering direct flights into Louisville but all major carriers do operate. You can often get deals from Going for cheap cash tickets to Louisville a few times a year but if you have specific travel dates, I recommend monitoring your flights on Google Flights.

For this itinerary, I’d recommend staying in the Louisville area. With such a brief trip it’s important to maximize your time and this will be a great way to do that.

Check out my guide to where to stay on the Kentucky bourbon trail for hotel suggestions!

Save money and time by skipping checking luggage and packing a carry-on backpack for this trip. Book an early morning flight to arrive in Louisville in time to catch the 4:00 distillery tour at Old Forester on Whiskey Row.

The Old Forester tour includes all stages of the bourbon-making process, an excellent bourbon tasting, and products in the gift shop you can’t find anywhere else that are always in stock. Tickets for the Old Forester Tour open three months in advance, so be sure to put it on your calendar to snag your ticket!

Pro Tip! Be sure to snag some modjeskas, a Louisville dessert staple, at the Old Forester gift shop. They are amazing and hard to find anywhere else!

After your tour, get ready to be greeted with many of the wonderful culinary experiences Louisville has to offer with dinner at the Village Anchor. Known for their wide selection of bourbons on the menu and quality food, this place is certainly one to try. You can also try Proof on Main – another great cocktail bar not far from your Old Forester experience.

Day 2: Explore the Urban Bourbon Trail and surrounding area

Start your morning at one of my favorite breakfast spots, The Cafe. While there, you can browse the Louisville Stoneware for a keepsake to bring home, too.

After breakfast, head back to Whiskey Row for a morning of new-age bourbon. Start your experience at Rabbit Hole, one of the most up-and-coming brands. You can book your reservation for Rabbit Hole 8 weeks in advance. I love their gift shop because it has super unique cocktail and bourbon products. So be sure to arrive early to give yourself some time to wander about before your tour starts.

Continue your Louisville bourbon experience by walking just 0.4 miles to Angel’s Envy. Tours open 8 weeks in advance with a variety of unique experiences to choose from. After completing two standard tours up to now, I’d recommend a 12:45 Taste the Finish experience. With bourbons known to excite enthusiasts, Angel’s Envy is a great place to try something different.

It’s time to head out of Louisville and drive just 30 minutes down the highway to Shelbyville, Kentucky. Shelbyville is an up-and-coming bourbon destination (and my hometown). Bulleit recently expanded to this new distilling location that has high-end finishes, good cocktails, and a quality product, too. If the days of the week work, consider a cocktail class. Bulleit is known by bartenders as a cocktail-making favorite.

After your final stop for the day check out the Bell House for dinner, Shelbyville’s fan favorite. You’ll likely need a reservation, especially on the weekend. Be sure to get a Kentucky staple, the Kentucky Hot Brown here. It’s fantastic and will give you a great look at a classic dish.

Day 3: Venture out to Bardstown

Wake up early to drive from Louisville to Bardstown, Kentucky. A quaint town, known for its large amount of major brand and craft distilleries. The drive is only about 50 minutes and pretty scenic.

Start your day at Heaven Hill Distillery at the Do Your Own bourbon experience. This tour gives you the opportunity to taste exclusive products and choose to bottle your own. This experience is super unique and will give you the option to buy a hard-to-find bourbon at the end. Before the tour be sure to give yourself time to explore the new Heaven Hill Bourbon Experience, with interactive galleries and a movie theatre.

After your Do Your Own class, head down the road (literally) to Bardstown Bourbon Company for lunch. The restaurant offers a wide selection of southern favorites, like chicken and grits and bread pudding. You will need a reservation, so be sure to book one in advance. Bardstown Bourbon Company has some of the most unique operations, with modern facilities and an interesting business model. After lunch explore one of the many unique experiences offered here. I did the rick house thieving tour and it was a great price for the experience offered. Highly recommend!

Depending on your schedule, you could visit Willett in Bardstown before heading out of town. A guided tour can be booked 90 days in advance and offers a unique look at a smaller operation with quality product. Willett is a beautiful location with great products, too. It’s the perfect stop for nice photo opts of your amazing trip on the Bourbon Trail!

Best places to stay on the bourbon trail

With just a 3-day itinerary, I’d highly recommend staying in Louisville. Here are some hotel recommendations in downtown Louisville to make it easy to get around most of the distilleries included in the itinerary.

Moxy Louisville

A Marriott hotel, the Moxy Louisville Downtown is located right off Whiskey Row within walking distance of many of the downtown Louisville distilleries. The best part about the Moxy is it can be really affordable for its location, costing as little as $110 a night. 

21c Hotel Louisville

One of my favorite hotel chains, the 21c is part art museum and part modern hotel. The Louisville 21c is located near the Louisville Slugger Museum and Factory and is a great location for shopping and dining. Be warned: the 21c chain is not cheap but the experience of staying at one is something everyone should do in their lifetime. If you don’t choose to stay here, you can visit the modern art galleries for free and eat at their world-class restaurant. 

Hyatt Regency Louisville

Hyatt fans can find a couple of options in the Louisville area including the Hyatt Regency downtown. The downtown Regency is listed as a Category 4 hotel but it’s best to pay cash here.

Explore on. -K