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Bluegrass Elegance: Horses, History & Heritage

Bluegrass Elegance: Horses, History & Heritage image

May 6-13, 2026

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Bluegrass Elegance: Horses, History & Heritage

Discover the beauty and traditions of Kentucky on this journey through Louisville and Lexington. Experience the excitement of Churchill Downs with a behind-the-scenes museum tour, a special Derby “Hatitude” event, and an afternoon of live racing in Millionaires Row. Explore Louisville’s treasures with visits to the Louisville Slugger Museum, a scenic Ohio River dinner cruise, and the Muhammad Ali Center. In Lexington, step into horse country at Keeneland and the Kentucky Horse Park, while also enjoying the charm of Ashland, the Henry Clay Estate. Savor Kentucky’s famed bourbon heritage at Woodford Reserve, indulge in southern dining, and relax in elegant accommodations throughout this unforgettable adventure.

Pricing for this tour is:

Solo Traveler per person: $5799

Double Travelers per person: $4999

$250 Deposit due at booking; final payment is due 2/6/2026

Journey Highlights

Journey Highlights image

At a glance

Day 1 - Arrive in Louisville, KY

06-May-2026
Day 1 - Arrive in Louisville, KY image

Arrive in Louisville and Settle In

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Arrival in Louisville

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.
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Drury Inn & Suites North

We will check into the Drury Inn & Suites North, a comfortable and well-appointed property offering excellent amenities.
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Dinner at Malone’s

This evening we will enjoy dinner together at Malone’s, located conveniently near the hotel.
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Evening at Leisure

This first evening is a chance to relax after a day of travel and prepare for the extraordinary experiences that lie ahead.

Day 2 - Churchill Downs, Hermitage Farm, and Derby Traditions

07-May-2026
Day 2 - Churchill Downs, Hermitage Farm, and Derby Traditions image

Churchill Downs, Hermitage Farm, and Derby Hatitude

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Breakfast

Following breakfast, our day begins with a visit to the legendary Churchill Downs, home of the Kentucky Derby.
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Visit to Churchill Downs & Kentucky Derby Museum

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.
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Hermitage Farm Tour and Lunch

We will venture to Hermitage Farm for an insightful tour and an included lunch, providing a glimpse into the equestrian traditions that define Kentucky.
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Lunch at Hermitage Farm

Enjoy an included lunch at Hermitage Farm during the tour.
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Hatitude Experience at Churchill Downs

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.
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Drury Inn & Suites North

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.
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Drury Inn Kickback Dinner

Enjoy the Drury Inn’s complimentary Kickback Dinner.

Day 3 - Historic Homes and the Thrill of Racing

08-May-2026
Day 3 - Historic Homes and the Thrill of Racing image

Conrad-Caldwell House and Churchill Downs Racing

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Guided tour of Conrad-Caldwell House Museum

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.
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Live Racing at Churchill Downs

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.
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Elegant Luncheon in Millionaires Row

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.
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Dinner at a local restaurant

The day concludes with dinner at a local restaurant before we return to our hotel.

Day 4 - Sluggers, Distilleries, and a Riverboat Cruise

09-May-2026
Day 4 - Sluggers, Distilleries, and a Riverboat Cruise image

Louisville Slugger, Bourbon, and Riverboat Dining

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Louisville Slugger Museum & Factory visit

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.
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Free time and lunch at 4th Street Live

Enjoy free time and lunch on your own at the lively 4th Street Live entertainment district.
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Nulu Whiskey Distillery tour

Step back into the atmosphere of Prohibition during a fascinating distillery tour at Nulu Whiskey, where Kentucky’s renowned bourbon heritage is highlighted.
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Rest at hotel

Following a brief rest at our hotel.
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Belle of Louisville Riverboat dinner cruise

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.

Day 5 - Muhammad Ali Center and Lexington Heritage

10-May-2026
Day 5 - Muhammad Ali Center and Lexington Heritage image

Muhammad Ali Center and Ashland Estate Tour

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Guided visit to Muhammad Ali Center

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.
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Tour of Ashland, the Henry Clay Estate

Afterward, we head 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.
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21c Museum Hotel Lexington

In the late afternoon we check into the 21c Museum Hotel Lexington, a unique boutique property that combines contemporary art with elegant accommodations.
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Dinner at Carson’s

This evening we gather for dinner at Carson’s, a local favorite known for its warm atmosphere and excellent cuisine.

Day 6 - Keeneland, Woodford Inn, and Bourbon Country

11-May-2026
Day 6 - Keeneland, Woodford Inn, and Bourbon Country image

Keeneland Workouts, Woodford Reserve, and Fine Dining

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Breakfast at Keeneland Track Kitchen

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.
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Guided tour of Keeneland morning workouts

A guided tour of the morning workouts where Kentucky’s finest thoroughbreds are put through their paces.
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Lunch at the Woodford Inn

We travel to the charming Woodford Inn in Versailles for a leisurely lunch.
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Visit to Woodford Reserve Distillery

Visit the renowned Woodford Reserve Distillery, a National Historic Landmark providing insight into the craftsmanship and tradition of Kentucky bourbon making.
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Dinner at Granddam

Dinner this evening is reserved at Granddam, a celebrated restaurant housed within a historic warehouse district, offering refined regional cuisine.

Day 7 - Kentucky Horse Park and Equestrian Culture

12-May-2026
Day 7 - Kentucky Horse Park and Equestrian Culture image

Kentucky Horse Park, Champions Show, and Farewell Dinner

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Visit to Kentucky Horse Park

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.
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Horse-drawn trolley ride

We begin with a horse-drawn trolley ride before attending the Hall of Champions Show and Equine Showcase, where world-class horses are presented.
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Hall of Champions Show and Equine Showcase

Attend the Hall of Champions Show and Equine Showcase, where world-class horses are presented.
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Bluegrass luncheon

A Bluegrass luncheon is included.
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Free time at Kentucky Horse Park museums

Guests may enjoy free time to explore the International Museum of the Horse and the American Saddlebred Museum.
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Return to hotel for relaxation

This afternoon we return to our hotel for relaxation before gathering for a special farewell dinner.
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Farewell dinner at local Lexington restaurant

Gather for a special farewell dinner at a local Lexington restaurant.

Day 8 - Return Home

13-May-2026
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Return Journey and Farewell Lunch

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Breakfast at hotel

Start off with another great breakfast at the hotel before we climb aboard the coach fand head for the airport!

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Return home on Alaska Airlines

We will return home on this day and board our coach for return drop offs.

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Map

1. Drury Inn & Suites North

9597 Brownsboro Rd, Louisville, KY 40241

2. Malone’s

4370 Summit Plaza Dr, Louisville, KY 40241

3. Churchill Downs & Kentucky Derby Museum

700 Central Ave, Louisville, KY 40208

4. Hermitage Farm

10500 W US Highway 42, Goshen, KY 40026

5. Conrad-Caldwell House Museum

1402 St James Ct, Louisville, KY 40208

6. Louisville Slugger Museum & Factory

800 W Main St, Louisville, KY 40202

7. 4th Street Live!

411 S 4th St, Louisville, KY 40202

8. Nulu Whiskey

436 Baxter Ave, Louisville, KY 40204

9. Belle of Louisville Riverboats

401 W River Rd, Louisville, KY 40202

10. Muhammad Ali Center

144 N 6th St, Louisville, KY 40202

11. Ashland, The Henry Clay Estate

120 Sycamore Rd, Lexington, KY 40502

12. 21c Museum Hotel Lexington

167 W Main St, Lexington, KY 40507

13. Carson’s Food & Drink

362 E Main St, Lexington, KY 40507

14. Keeneland

4201 Versailles Rd, Lexington, KY 40510

15. Woodford Inn

140 Park St, Versailles, KY 40383

16. Woodford Reserve Distillery

7785 McCracken Pike, Versailles, KY 40383

17. Granddam

101 W Loudon Ave, Lexington, KY 40508

18. Kentucky Horse Park

4089 Iron Works Pkwy, Lexington, KY 40511