Experience the best of Kentucky on a journey through its storied landscapes, timeless traditions, and legendary hospitality. Begin in Louisville with exclusive access to Churchill Downs, the Kentucky Derby Museum, and the thrill of live racing in Millionaires Row. Explore the Muhammad Ali Center, discover baseball history at the Louisville Slugger Museum, and enjoy a scenic dinner cruise on the Ohio River. In Lexington, step into horse country with visits to Keeneland, the Kentucky Horse Park, and the historic Ashland Estate. Savor the state’s world-famous bourbon during a tour and tasting at Woodford Reserve and indulge in southern cuisine along the way. This immersive tour captures the spirit, charm, and cultural heritage that make Kentucky truly unforgettable.

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Our journey begins in the early hours of the morning as we gather at designated pick-up locations and make our way to Portland International Airport for our flight to Louisville, Kentucky. Upon arrival, we are welcomed into the Bluegrass State, where tradition and southern charm are ever-present. We will check into the Drury Inn & Suites North, a comfortable and well-appointed property offering excellent amenities. This evening we will enjoy dinner together at Malone’s, located conveniently near the hotel. This first evening is a chance to relax after a day of travel and prepare for the extraordinary experiences that lie ahead. (D)

Following breakfast, our day begins with a visit to the legendary Churchill Downs, home of the Kentucky Derby. Here we will enjoy an introduction to the rich history of thoroughbred racing at the Kentucky Derby Museum. From there, we will venture to Hermitage Farm for an insightful tour and an included lunch, providing a glimpse into the equestrian traditions that define Kentucky. In the afternoon, we return to Churchill Downs for the delightful “Hatitude” experience, where guests will have the opportunity to design their own Derby-style hats, a tradition deeply intertwined with the spirit of the race. This evening we return to our hotel to enjoy the Drury Inn’s complimentary Kickback Dinner, followed by leisure time to rest or further explore Louisville at your own pace. (B, L, D)

This morning begins with a guided tour of the Conrad-Caldwell House Museum, a beautifully preserved mansion that reflects Louisville’s historic grandeur. Known as “Conrad’s Castle,” the home showcases fine architecture and the lifestyle of one of the city’s most prominent families during the Victorian era. Following this, we return to Churchill Downs for an extraordinary afternoon of live racing. Our group will dine in style with an elegant luncheon in Millionaires Row, an exclusive space offering excellent views of the track and a refined atmosphere. There is nothing quite like the excitement of the horses thundering past as you take in the energy of the crowd. The day concludes with dinner at a local restaurant before we return to our hotel. (B, L, D)

This morning, we begin at the Louisville Slugger Museum & Factory, an iconic attraction where the famous baseball bats are crafted. Guests will discover the artistry and history of this American pastime before enjoying free time and lunch on their own at the lively 4th Street Live entertainment district. Later, we step back into the atmosphere of Prohibition during a fascinating distillery tour at Nulu Whiskey, where Kentucky’s renowned bourbon heritage is highlighted. Following a brief rest at our hotel, the evening brings a true highlight—a dinner cruise aboard the Belle of Louisville Riverboat. This beautifully restored vessel carries us along the Ohio River with fine dining, live music, and captivating city views. (B, D)

We begin the day with a guided visit to the Muhammad Ali Center, a world-class museum dedicated to the life, values, and legacy of “The Greatest.” Through interactive exhibits, films, and galleries, we gain an appreciation for the man who transcended the sport of boxing to become a global humanitarian. Afterward, we enjoy a boxed lunch before continuing to Lexington, where we will tour Ashland, the Henry Clay Estate. This historic site reveals the life and influence of the “Great Compromiser,” whose contributions shaped American history. In the late afternoon we check into the 21c Museum Hotel Lexington, a unique boutique property that combines contemporary art with elegant accommodations. This evening we gather for dinner at Carson’s, a local favorite known for its warm atmosphere and excellent cuisine. (B, L, D)

Today begins with a truly memorable experience at Keeneland. We enjoy breakfast at the Track Kitchen, a favorite among jockeys and trainers, followed by a guided tour of the morning workouts where Kentucky’s finest thoroughbreds are put through their paces. Later, we travel to the charming Woodford Inn in Versailles for a leisurely lunch before visiting the renowned Woodford Reserve Distillery. This National Historic Landmark provides insight into the craftsmanship and tradition of Kentucky bourbon making. Guests will experience the rich aroma of fermenting mash, the aging barrels, and the legacy of one of the world’s most respected bourbon brands. Dinner this evening is reserved at Granddam, a celebrated restaurant housed within a historic warehouse district, offering refined regional cuisine. (B, L, D)

Our final full day is devoted to celebrating Kentucky’s equestrian culture at the Kentucky Horse Park. This premier facility is dedicated to man’s relationship with the horse and features a variety of engaging activities. We begin with a horse-drawn trolley ride before attending the Hall of Champions Show and Equine Showcase, where world-class horses are presented. A Bluegrass luncheon is included, after which guests may enjoy free time to explore the International Museum of the Horse and the American Saddlebred Museum. This afternoon we return to our hotel for relaxation before gathering for a special farewell dinner at a local Lexington restaurant. (B, L, D)

After breakfast, we bid farewell to Kentucky and transfer to the Louisville Airport for our return flight. As we journey home, we carry with us memories of gracious southern hospitality, fascinating history, thoroughbred traditions, bourbon heritage, and the many shared experiences that made this journey so memorable. (B)