You arrive in Cincinnati today and transfer to The Clair Downtown, a stylish boutique hotel right in the heart of the city’s riverfront and entertainment district. Perfectly positioned for the days ahead, it’s an ideal base for evenings at the ballpark and exploring Cincinnati on foot. With no set plans this evening, you can ease into the trip with a relaxed stroll along the Ohio River or head into Over-the-Rhine for an early dinner and a drink. It’s a gentle, unstructured start, designed to leave you refreshed and ready for the baseball action to come.

Today is all about easing into Cincinnati before the first big night at the ballpark. You’ve got the freedom to explore at your own pace, whether that means lunch at Findlay Market, wandering the historic streets of Over-the-Rhine, or spending time at the National Underground Railroad Freedom Center. It’s a deliberately flexible day, giving you time to enjoy the city while keeping plenty in reserve for the evening ahead.

As night falls, make your way to Great American Ball Park for your first taste of Major League Baseball as the Cincinnati Reds take on the Los Angeles Dodgers. You’ll be seated in Premier Seating in Section 124, offering excellent sightlines close to the action and a great atmosphere as the stadium fills and the lights come up. With the riverfront setting and the buzz of a big matchup, it’s a classic American sports night and a real highlight of the trip.

Today is built around a deeper, behind-the-scenes baseball experience, giving you a real sense of what happens beyond the stands on game day. You head to Great American Ball Park for a Premier Game Day Experience, starting with a 90-minute Ultimate Game Day tour that takes you into areas normally off-limits to the public. You’ll visit the Scoreboard Operations Room, where you get a feel for what it’s like working in the booth and even create your own scoreboard message, before heading down to the Right Field Wall and the visitors’ bullpen for a closer look at the action from pitch level.
The experience continues with a guided tour of the Cincinnati Reds Hall of Fame and Museum, bringing the club’s history to life through legendary players, iconic moments and memorabilia. Before the stadium opens fully, you’ll also enjoy early access to watch the Reds’ pregame workout in its entirety from the Right Field Sun/Moon Deck, a fantastic vantage point to see the players up close as they prepare for the evening ahead.
As game time approaches, you take your seats once again in Premier Seating in Section 124 to watch the Cincinnati Reds face the Los Angeles Dodgers. After a full day immersed in the inner workings of the ballpark, the atmosphere feels even more special, rounding off your time in Cincinnati with a truly memorable night at Great American Ball Park.

After a full and immersive couple of days at the ballpark, this morning is kept deliberately relaxed. It’s your chance for some last-minute sightseeing in Cincinnati, whether that’s a final wander through Over-the-Rhine, a riverside coffee along the Ohio, or picking up a few souvenirs before leaving the city behind. There’s no early start, just time to enjoy the city at your own pace. In the early afternoon, you’re collected by private car for the journey south into Kentucky. The drive to Louisville takes around an hour and a half, giving you time to sit back and watch the scenery change as baseball territory gives way to bourbon country. On arrival, you check into Hotel Bourré Bonne, a characterful boutique hotel that leans into the city’s bourbon heritage while offering a refined, contemporary stay. Perfectly placed for distilleries, dining and evenings at Churchill Downs, it immediately sets the tone for the next stage of the journey. The rest of the day is free to unwind, explore locally, or enjoy a quiet first drink as Louisville becomes the cultural and experiential heart of the trip.

Today dives straight into Kentucky’s bourbon and racing heritage, but with a relaxed, well-paced flow. You start with a visit to the historic Stitzel-Weller Distillery, where a guided tour and tasting introduces you to one of the most influential names in bourbon history and sets the scene for the days ahead. From here, you move on to a BBQ and bourbon pairing lunch, a laid-back but flavour-packed experience that captures the essence of Kentucky cooking.
In the afternoon, there’s a stop at a local milliner, offering a nod to the traditions of horse racing and Derby style, before the evening takes centre stage. As the sun begins to dip, you head to Churchill Downs for night racing. With the track lit up under floodlights and the atmosphere building, it’s an unforgettable introduction to Louisville’s racing scene and a real highlight of your time in the city.

Today takes you deeper into the heart of bourbon country as you travel south into Bardstown, often referred to as the bourbon capital of the world. Your day begins at Bardstown Bourbon Company with an exclusive barrel thieving tour and tasting, a real insider experience that lets you sample bourbon straight from the barrel while learning how flavour, character and complexity develop over time. It’s an immersive and hands-on start to the day that sets the tone beautifully.

Lunch follows at the distillery, where you’re welcomed with a cocktail before sitting down to enjoy the restaurant’s seasonal menu. With gratuity included, it’s a relaxed and unhurried break that allows you to savour both the food and the setting. In the afternoon, you continue to Heaven Hill Distillery for their Whiskey Connoisseur Experience, offering deeper insight into one of Kentucky’s most respected producers and the opportunity to taste some outstanding expressions.

The day finishes on a lighter, more creative note at Lux Row Distillers, where a guided mixology class shows how bourbon comes into its own in a cocktail, blending tradition with a modern twist. You return to Louisville in the early evening, having enjoyed a full but well-balanced day that brings bourbon to life from barrel to glass.

After a full few days immersed in bourbon and racing, today slows the pace while still delivering some truly special experiences. You begin with a boozy brunch at a local restaurant, where a relaxed limited menu is paired with a cocktail, giving you a chance to ease into the day and recap the highlights so far.

From here, you head into Kentucky’s horse country for an exclusive private visit to Kismet Thoroughbred Farms. This behind-the-scenes tour offers rare insight into the world of elite thoroughbred breeding, with time to explore the farm, learn about the bloodlines and understand what goes into producing some of the sport’s most impressive horses.

The day concludes with a visit to Woodford Reserve Distillery for their Path to Flavor tour and tasting. Set among rolling countryside, it’s a fitting and elegant way to round off your bourbon journey, bringing together craftsmanship, setting and flavour before returning to Louisville for a relaxed final evening.

After breakfast, it’s time to say goodbye to Kentucky and bring the journey full circle. You’re collected by private car for the transfer back to Cincinnati airport, a comfortable and unhurried drive that gives you time to reflect on the past week. From premier baseball nights and behind-the-scenes stadium access to bourbon barrels, horse farms and floodlit racing, it’s been a journey packed with standout experiences and unforgettable moments. You arrive at the airport in good time for your onward flight, bringing this sports-and-spirits adventure to a close.