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.

Kentucky is renowned for its horse programs and farms, this is your chance to see the prestigious facilities up close. Tour area horse farms—some that are usually closed to the public—to get a look at the work that goes into raising and caring for thoroughbreds. The tour includes time to meet and interact with the horses, maybe even feed them their favorite peppermint treats.

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.

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.

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. ✨

A VIP Bourbon Tour is more than just a visit to a distillery—it’s a curated, luxury experience designed for true bourbon enthusiasts. With private transportation, personalized guidance from expert hosts, and exclusive access to historic areas and rare bourbon tastings, a VIP tour elevates every moment. Choosing a VIP tour means skipping the crowds, enjoying tailored insights into the distillation and aging process, and sampling select or limited-edition bourbons not available on standard tours. It’s perfect for those who want an immersive, educational, and sophisticated experience that combines comfort, style, and a deeper appreciation of Kentucky’s bourbon heritage.

Explore the heart of Kentucky's rich bourbon heritage with SIP Tours on our exclusive private tour of the world-renowned Kentucky Bourbon. This personalized journey offers an immersive experience into the craftsmanship and history behind America's native spirit. Tour Highlights: Custom Itinerary: Tailored to your preferences, visit iconic distilleries such as Buffalo Trace, Woodford Reserve, Bulleit, and more. VIP Access: Enjoy exclusive tastings, behind-the-scenes tours, and meet master distillers who share their expertise and passion for bourbon making. Scenic Landscapes: Traverse picturesque Kentucky countryside known for its rolling hills and historic distillery architecture. Details: Embark on a memorable journey through Kentucky's Bourbon Country with SIP Tours, where every sip tells a story of tradition, craftsmanship, and Southern hospitality.

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.

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.

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.

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.

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.

Experience the perfect blend of Kentucky tradition, history, and craftsmanship with our Churchill Downs & Buffalo Trace Bourbon Tour. This carefully curated experience brings together two of the most iconic symbols of the Bluegrass State: thoroughbred horse racing and world-class bourbon. The tour begins with a visit to Churchill Downs, home of the legendary Kentucky Derby. Guests will explore the historic grounds and museum, learning about the rich legacy of thoroughbred racing, the pageantry of Derby Day, and the deep cultural roots that make this venue world-famous. From there, the journey continues to Buffalo Trace Distillery, one of the oldest continuously operating distilleries in the United States and a cornerstone of the Kentucky Bourbon Trail. During the guided distillery tour, guests will discover the bourbon-making process from grain to bottle, walk through historic warehouses, and gain insight into the craftsmanship behind some of the most renowned bourbons in the world.

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.

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.

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

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!

Discover the rich heritage of bourbon with guided tours through Kentucky's iconic distilleries. Every stop reveals the artistry behind bourbon-making, complemented by Southern hospitality. Travel in luxury, whether you're part of a romantic couple’s retreat or a lively group of friends, aboard stylish SUVs or spacious buses. Each tour includes round-trip transportation, distillery admissions, and complimentary snacks and water for a comfortable experience. Perfect for couples, friends, or corporate events, this tour invites you to sip and savor the finest bourbons while enjoying the scenic landscapes of bourbon country. - Guided tours through Kentucky's renowned distilleries - Luxury transportation options for groups of all sizes - Round-trip transport, distillery admissions, and snacks included - Ideal for couples, friends, and corporate retreats

Fans of David Dominé’s “A Dark Room in Glitter Ball City” can visit locations and sights where this true-crime memoir is set with this unique themed walking tour. Join the author and small group for a narrated stroll past highlights like the Conrad-Caldwell Mansion on St. James Court, plus pop into a local bar mentioned in the book for a drink. Take home an autographed copy of the book plus a sweet treat as souvenirs.

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.

Taste your way through the East End of Lexington and learn about local lore with the help of a tour guide passionate about the neighborhood’s best food and drink. On this 2.5-hour tour, the group leader will share some of their own favorite watering holes, and you can eat like a real Lexingtonian.

Louisville is a city where every meal tells a story, and every glass holds a piece of history. Known as the Bourbon City, your local guides invite you to step away from the tourist paths and dive into the authentic flavors that make this river town truly unique. Your Louisville food tour explores the vibrant revival of Downtown, focusing on the cast-iron beauty of Whiskey Row and the cultural energy of Museum Row.