Top Louisville Holidays

Be transported back to Louisville during the Prohibition era and learn about the city’s haunted past as you discover speakeasies, a ghost-infested hotel, and other important landmarks. Stop for local bites at four venues and enjoy prohibition-era cocktails as well as a bourbon tasting while learning about prohibition history. End with a dessert and a cocktail with a view overlooking downtown Louisville.

Old Louisville is home to impressive Victorian mansions that trace back to wealthy families in the 1800s. On this walking tour, uncover the eerie past of the neighborhood alongside a guide who regales you with several ghostly tales. Stop at several points of interest including the Conrad-Caldwell House Museum, the Witches' Tree, and the Filson Historical Society.

Uncover the sordid past and rich history of Louisville on a ghost tour through the city's old town. Walk past impressive Victorian mansions and old buildings, listening to stories about their otherworldly residents. See the Filson Historical Society, the Conrad-Caldwell House Museum, Louisville's Central Park, and the Witches' Tree.

Step back in time and discover the history of Louisville during an immersive walking tour through the historic center. Listen to stories of wealthy titans who used to roam the streets as you explore sights including St. James Court, Ormsby Avenue, Floral Terrace, and Millionaires Row. You also have the chance to admire the old Victorian architecture that dots the neighborhood.

Discover Kentucky's long bourbon-making history on a half-day tour. Choose three distilleries to visit from a list of over 15 and spend your day taking guided tours of the facilities. Learn about the production process of making bourbon as well as the tumultuous history of distilling during the Prohibition. You also get to sample several bourbons from each brand at the end of every tour.

Discover the rich history and beautiful architecture of Old Louisville as you embark on a walking tour through the city. Walk past impressive Victorian homes, once owned by wealthy families from the bourbon, tobacco, and racetrack industries, and learn about their history. You also stop at several points of interest including the Witches' Tree, Conrad's Castle, the Filson Historical Society, and Central Park.

If downtown Louisville is your stage for an unforgettable night, then let this private party bus do all of the driving for you. You’re free to drink, dine, and dance your heart out thanks to a dedicated chauffeur who will take you wherever your party desires. Connect your phone to the bus’s sound system and rock out to your favorite music. Prices vary depending on duration of the bus rental.

Sipping in the South was born from a bold idea: bourbon deserves more than a bus ride, a stamp in a book, and a cookie-cutter, self-guided checklist. That’s where we come in. We’re the local experts who take the trail less traveled, curating exclusive experiences with up to 5 handpicked distilleries. We book the best each one has to offer rare tastings, sipping straight from the barrel with the owner, blending your own bourbon, or mixing your own cocktail. The Kentucky Bourbon Trail® is a nice start, but it’s not the whole story. It features a select group that pay to participate — but some of Kentucky’s best experiences aren’t even on their map. We’re here to change that. Every tour begins with our Private Bourbon 101 Social — a hands-on introduction to nosing and sipping that gives you the tools to truly enjoy what you’re tasting. Because when you understand bourbon, everything else gets better. And yes — we even save 30 minutes for rare finds at local liquor stores.

This tour requires 8 passengers to book. This tour is all about you! We customize the itinerary based upon your preferences and availability of the distilleries. Have an awesome time with your friends at truly memorable distilleries and learn about Kentucky’s rich history in bourbon with a full-day bourbon tour. We will pick you up at your hotel or bed and breakfast and take you for a full day of fun and learning. We provide the water, soda, and light snacks during the day so you don’t get tired! You’ll receive a guided tour or tasting at three distilleries, depending on availability. If you have an absolutely must-see distillery, you may want to check now to see if they have availability. Otherwise, leave it to our experts in fun and bourbon to plan it for you.