Top Kentucky Private and Luxury

Discover the heart and soul of Kentucky’s beautiful Bluegrass horse country on this guided half-day small-group tour. Get a behind-the-scenes look at the thoroughbred horse lifestyle as you explore the famous Keeneland Race Course and one or more thoroughbred horse farms. Learn about the history of racing and how Lexington became the epicenter of thoroughbred breeding in the United States. Note: itinerary may change depending on availability.

Attractively priced at $10 per person for groups of 5 to 15, this EXCLUSIVE tour is for those who don't have much time, but still want to see and learn a lot about the fascinating Old Louisville neighborhood. Only 1 or 2 in your party? No worries, you can still book this as a private tour! At the pace YOU set, stroll shady walking courts in the gas-lamp district and down the city's old Millionaires Row where bourbon barons, racetrack royalty, and the titans of tobacco made their homes. Landmarks you'll admire from the sidewalks include the Samuel Culbertson Mansion, Conrad's Castle, the William Wathen House, the Pink Palace, and the emblematic Fountain at St. James Court. On this jaunt you'll be treated to a treasure trove of grand architecture from the late 1800s, including stunning examples of Richardsonian Romanesque and Renaissance Revival styles, not to mention many variations on the Italianate, Châteauesque, Queen Anne, Federal, Neo-Georgian, and Arts & Crafts genres.

Get to know the charms of Lexington as you eat your way through the Kentucky city’s downtown on this walking food tour. You’ll learn all about the history and culture of the “Horse Capital of the World” as your guide shares insights about the landmarks you pass. The tour will make five stops and includes food ranging from traditional Kentucky specialties to modern innovations.

Are you a fan of The Godfather? Goodfellas? Scarface? The Sopranos? The Untouchables? Casino? Boardwalk Empire? A Bronx Tale? If you love mobster movies, then this is the tour for you! This is the only tour about the "Sin City" years of Newport where you can view all of the historic sites from the comfort of an air-conditioned vehicle (minivan). This allows us to explore far more historic sites in less time than a walking tour can! You will relax from the comfort of your seat while you are transported from site-to-site and will learn all about the unique history of each site, it's connections with the mafia, illegal gambling, bootlegging, and prostitution that earned Newport the name "the sin city of the south"! You will also have an opportunity to get out of the vehicle at each tour stop and do some exploring of your own, with your tour guide there to answer any questions you may have.

Our Bourbon Tour offers a personalized and authentic experience in the heart of bourbon country. Guests can choose three of the finest distilleries, selected based on availability and personal preferences, where they will enjoy guided tours, tastings, and a deep dive into the rich history and craftsmanship of bourbon. The tour can be arranged with private luxury transportation for a more exclusive experience, or with public transportation for groups of up to 11 people, always ensuring a smooth, comfortable, and well-organized journey. Every detail is thoughtfully designed to deliver a memorable experience, combining flexibility, comfort, and exceptional service from start to finish. ✨

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.

There are so many whiskey distilleries across the Louisville area that it can be tough to know where to start when you’re planning your trip solo. Instead of stressing out about your itinerary, on this full-day guided tour, visit a curated selection of bourbon spots across the region and sample some of Louisville’s most popular beverages.

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.

This is not your average bourbon tour—it’s a fully immersive, luxury-crafted bourbon experience unlike anything else. Over three unforgettable days, you’ll travel in a private Maybach Executive Sprinter Van, stay at the exclusive Barrel Proof Bed & Breakfast, and enjoy curated dining and fireside bourbon socials. What truly sets this apart? You and your group will hand-select a private barrel of bourbon, then bottle and seal your personal share—complete with custom labels to take home. You’ll visit iconic distilleries with the choice to either enjoy tastings at 3–4 top spots or opt for one exclusive behind-the-scenes private tour. Every moment is tailored for comfort, connection, and craftsmanship. Perfect for bourbon collectors, group getaways, or milestone celebrations, this is a one-of-a-kind journey into the heart of Kentucky bourbon country—where luxury meets tradition.

Spend a fun-filled three hours in Lexington’s historic Distillery District with a local foodie guide who’ll help you taste your way through town. Learn all about the history of the city and its culture as you sample everything from expertly blended cocktails to Kentucky staple burgoo stew. And for dessert, you’ll try some award-winning ice cream.

Discover Historic Old Louisville's rich architectural heritage on this walking tour that showcases the nation's largest contiguous Victorian Mansion district. Follow your guide through history-rich streets as they reveal the history behind these beautiful buildings and the surrounding area, and answer any questions you may have about the history and culture of Louisville.

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.

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.

Explore Cincinnati without having to walk on this sightseeing bus tour. Enjoy a multimedia presentation with more than 1,000 historic photos and videos that show the development of the city as the bus drives around past landmarks that include Fountain Square, Paul Brown Stadium, Great American Ball Park, Findlay Market, and more.

Experience the most future-favoring tour on the Kentucky Bourbon Trail Craft Tour®! Unravel the mysteries of distillation, hear tales of circus life, and get the tall tale story of how two childhood friends came together to build a distillery through luck, bartering, and Craigslist finds. Tours always include a tasting of our Oak Eye Kentucky Bourbon, the ever-popular hazelnut liqueur, our fine rums, and maybe even a couple of moonshines.

Step into our nursery and meet the newest members of the Pin Oak family. You’ll stroll through the foaling barn, visit nursery paddocks, and get time petting curious foals and treating our broodmares to peppermints! Along the way, you’ll learn how we breed, raise, and care for these future champions, and what it takes to give them the happiest, healthiest start in life. This 60–75 minute guided experience includes: -The Foaling Barn: See where our foals take their very first steps -Nursery Paddocks: Spend time with mares and foals around their paddocks -Peppermint Time: Hand-feed treats to our broodmares and pet the foals -Breeding & Care Insights: Discover the daily routines and expert care that shape future athletes

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.

Enjoy two hours of chilling tales and spooky stories on this small-group walking tour around Covington, Kentucky. After learning about the gruesome history of the Roebling Suspension Bridge at the Roebling Murals, move on to discover the city’s macabre history at such stops as the former Newport Civil War Army Barracks and Carneal House Inn, said to be haunted by the enigmatic ‘Gray Lady’. Fans of the paranormal and true crime rejoice

This Bourbon Tour combined with a chocolate factory visit is designed for those who want to explore the heart of bourbon country while indulging in one of Kentucky’s most iconic treats : Bourbon Balls. The experience begins with guided visits to iconic distilleries along the Kentucky Bourbon Trail, where guests learn about the bourbon-making process, its centuries-old heritage, and the techniques that make this spirit world-renowned. Each distillery offers a unique perspective, complete with curated tastings and in-depth explanations led by knowledgeable guides. As a perfect complement, the tour includes a visit to the historic chocolate factory responsible for crafting the famous Bourbon Balls supplied to distilleries and specialty shops. Guests will discover the artisanal chocolate-making process—from tempering and molding to filling with bourbon—while enjoying exclusive tastings of their signature.

Explore vibrant NuLu & historic Butchertown with locally-owned Louisville Food Tours on the original Nulu food tour to taste the flavors of Louisville! Over the course of 3 immersive hours, you'll visit local eateries and enjoy delicious bites that showcase Louisville's culinary heritage. Dishes include biscuits & gravy with roots in the foothills of Appalachia, Kentucky-style fried chicken, a Louisville BBQ dish, bourbon balls, a Prohibition-era Hot Brown gravy, and barrel-aged craft beer. As you wander through the historic streets of two of Louisville's oldest neighborhoods, you’ll uncover the stories behind the city’s rich history, visit a historic home once occupied by Thomas Edison, sample a unique confection inspired by a Victorian actress, and trace the paths of the immigrants who shaped Louisville. This tour typically sells out. Reserve your spot early and come hungry!

Explore the heart of bourbon country on a 3-hour guided trolley tour through Louisville visiting six unique bourbon destinations. Enjoy exclusive access to tasting rooms and tour a bourbon distillery. This small group tour, capped at 12 guests, is Louisville's most unique bourbon tour. As you roll through vibrant neighborhoods like NuLu and Butchertown in a climate-controlled historic trolley, you'll enjoy 6 bourbon pours, 2 exclusive craft cocktails, and 6 bourbon-infused samples. Plus, your ticket includes a 24-hour LouHop pass so you can keep exploring downtown. This tour is perfect for both bourbon newcomers and seasoned enthusiasts. - Duration: 3 hours - 5 stops including a distillery tour and tasting rooms - 6 bourbon pours, 2 bourbon cocktails, and 6 bourbon-infused spice, sauce, and sweet samples - Exclusive access and custom crafted experiences not found elsewhere - Trolley: 24-hour LouHop pass included - Take-Home Gifts: Louisville Icons Tote bag & bourbon-smoked spice blend

Discover the dark, sordid past of Newport, Kentucky, located across the river from Cincinnati, on this guided tour. In the 1920s, the town had declared itself an independent municipality, free of state and federal controls, which attracted nefarious characters. Explore the streets and learn about the historical significance of Newport, and discover how this town gave birth to the modern-day gaming industry.

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 and aren't afraid to tell the real stories. This tour dives deep into the legendary Pappy Heist, led by none other than the mastermind himself. Its bold, unfiltered and straight from the source - a once in a lifetime experience you won't find in any tasting room brochure! The mastermind will be your guide for the day and every tour begins with our Bourbon 101 Social — an interactive, 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. We show you how they rolled it right out the distillery and the other juicy gossip. And yes — we even save 30 minutes for rare finds at local liquor stores.