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Kentucky Golf Trail Race Season Golf Holiday

5 Nights + 3 Rounds + Race Day

Experience a different side of American golf with this 5-night Kentucky Golf Trail Race Season small group tour, combining championship-style golf, bourbon country experiences and a VIP day at the world-famous Keeneland Racecourse. Based in Lexington at The Manchester Hotel, this USA golf holiday is designed for UK golfers who want more than just fairways, with private chauffeured transport throughout, hand-picked golf courses, immersive distillery visits and a rare insider’s look at Kentucky’s thoroughbred racing scene.

This golf and bourbon holiday is available during selected race season dates in April or October 2027, making it a brilliant option for golfers looking for a memorable spring or autumn golf escape to the United States. Play Frankfort Country Club, Greenbrier Country Club and Cherry Blossom Golf & Country Club, enjoy private tasting experiences at Castle & Key, Bluegrass Distillers and Town Branch Distillery, then spend an unforgettable afternoon at Keeneland with clubhouse dining and behind-the-scenes race day access.

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Bespoke golf tours with our personal stamp of approval

Our dedicated team of seasoned experts have played all the golf courses, stayed in every hotel, and explored each destination. From concierge-led service to bespoke itineraries crafted to your preferences, we ensure every detail is flawless. Whether you’re seeking exclusive golf tours or immersive non-golf experiences, our passion for excellence guarantees an unforgettable golf trip, every time.

Where You Will Stay & Play

average rating is 4 out of 5

Frankfort Country Club

Located in Kentucky’s capital city, Frankfort Country Club is a traditional private country club with a well-regarded golf course and a strong Bluegrass Region setting. The club sits at 101 Duntreath Street in Frankfort, placing golfers close to downtown, the Kentucky River, bourbon distilleries and the wider Lexington–Louisville corridor. The course is an 18-hole, par-72 layout designed by Scruggs & Hammond in 1973. Frankfort Country Club describes it as one of the best courses in Kentucky, with rolling hills, strong playing conditions and a layout that is friendly for a wide range of golfers thanks to its four tee boxes. From the course tour, the back tees stretch to 6,595 yards, with the routing using elevation changes, doglegs, bunkers, creeks, out-of-bounds areas and protected greens to create a round where accuracy and course management matter. The 10th hole is the signature moment: a scenic par 3 with an 80-foot drop from tee to green, protected by a creek and bunkers. Facilities include a practice range, large putting green, short-game area with practice bunker, full-service golf shop, club fitting, club repair and lessons from PGA professional staff. The club also offers dining, pool, fitness and racquet sports facilities, giving it a full country club feel beyond the course. For UK golfers, Frankfort Country Club works well as part of a wider Kentucky golf itinerary, especially for trips built around Lexington, Louisville, bourbon country, horse country and scenic Bluegrass golf.
average rating is 4 out of 5

The Manchester Lexington

Set in Lexington’s Historic Distillery District, The Manchester is a stylish independent boutique hotel with a strong sense of Kentucky character. The hotel has 124 guest rooms, including suites, and brings together warm interiors, bourbon-inspired details, high-end amenities and views across downtown Lexington and the wider Bluegrass Region. For golf travellers, The Manchester works well as a city-base hotel rather than a golf resort. Guests can stay close to Lexington’s restaurants, bars, distilleries, live music and horse-racing culture, while using the hotel as a comfortable base for rounds around Central Kentucky. VisitLEX highlights Lexington’s golf scene as affordable, scenic and playable for much of the year, with courses in the wider area including Kearney Hill Links, Gibson Bay, Cherry Blossom and other Bluegrass Region layouts. The hotel’s food and drink offering is a major part of the experience. Granddam is the hotel’s Bluegrass dining hall, while Lost Palm is a rooftop bar serving drinks and small bites with a lively, social feel. The hotel also lists a bespoke gym, flexible event space, high-speed Wi-Fi, airport/downtown shuttle service, EV charging and bicycle use as part of its wider amenities. The location is ideal for golfers who want more than just fairways. The Manchester places guests within the Historic Distillery District, with Rupp Arena, the Central Bank Center, the Lexington Farmer’s Market, Keeneland, Kentucky Horse Park and a wide choice of distilleries and breweries all within reach. It is a strong fit for a Kentucky golf holiday built around bourbon, horse country, downtown Lexington and scenic Bluegrass golf.
average rating is 4 out of 5

Cherry Blossom Golf Club

Located in Georgetown, just north of Lexington, Cherry Blossom Golf Club is an award-winning Central Kentucky golf venue with a polished country club feel. The club sits within the Cherry Blossom community and is based at 150 Clubhouse Drive, making it a practical choice for golfers staying in Georgetown, Lexington or travelling through Kentucky’s Bluegrass Region. The course is an 18-hole championship layout with five tee options, giving it good flexibility for different handicaps and mixed-ability groups. Cherry Blossom’s own golf information highlights its scenery, tournament use, outings and PGA qualifier credentials, while course listings describe it as a par-72 layout stretching around 6,866 yards from the back tees. Designed by Clyde Johnston, the course opened in the early 2000s and makes good use of Kentucky’s rolling terrain. The layout is generally playable but still asks for accuracy, with water, bunkering and approach-shot strategy becoming especially important across the closing stretch. Top 100 Golf Courses notes the course is routed around Lane’s Run Creek, with water playing a stronger role on the back nine and a demanding final hole. Facilities include a clubhouse, restaurant, golf shop, pool, driving range, putting green and teaching professional, giving Cherry Blossom a broader country club feel rather than just a standalone golf course. For UK golfers, Cherry Blossom works best as part of a Lexington or Kentucky golf itinerary, combining well with horse country, bourbon experiences, historic Georgetown and nearby courses around the Bluegrass Region. VisitLEX describes Lexington as a destination known for bourbon, farm-to-table food and horse country views, while Georgetown and Scott County tourism highlights Kentucky Horse Park, Old Friends Thoroughbred Retirement Farm and its Victorian-era downtown.
average rating is 4 out of 5

Greenbrier Golf & Country Club

Located on Bahama Road in Lexington, Greenbrier Golf & Country Club is a private golf and country club in Kentucky’s Bluegrass Region. The club offers a peaceful setting just minutes from the Hamburg area, giving golfers a quieter country club feel while still staying close to Lexington’s hotels, restaurants and wider city attractions. The main golf course is an 18-hole, par-72 layout measuring around 6,754 yards from the back tees. Course listings note a slope rating of 133–134, so while Greenbrier is not the longest course in Kentucky, it still offers a solid test for regular golfers. Tree-lined sections, water features, bunkering and a mature club setting make it a good option for players who enjoy traditional American country club golf with an emphasis on accuracy and steady course management. Greenbrier is particularly useful for golfers building a Lexington itinerary. The club’s facilities include casual and fine dining, a renovated clubhouse, swimming, fitness facilities, outdoor patio areas, practice facilities, four Trackman simulators, a PuttView putting green and a 19-acre fishing lake. That gives it strong appeal beyond the course, especially for members, guests and groups looking for a social club atmosphere around the golf. For UK golfers, Greenbrier is best suited as part of a wider Kentucky golf holiday based around Lexington or Louisville. Lexington adds plenty away from the fairways, including horse country, bourbon distilleries, farm-to-table dining and Bluegrass scenery, making it a strong destination for travellers who want golf mixed with proper Kentucky character.

All trips and itineraries can be adjusted to your requirements

The Itinerary

Day 1 – Arrive in Lexington

Arrive at the airport, where your private chauffeured transport will be waiting to take you to The Manchester Hotel in Lexington.


After checking in, settle into your hotel and enjoy your first evening in Kentucky. A suggested dinner option is Granddam at The Manchester, a stylish restaurant within the hotel and a Michelin One Key recipient.


Overnight: The Manchester Hotel


Day 2 – Golf at Frankfort Country Club & Castle & Key Distillery

Start your first full day in Kentucky with morning golf at Frankfort Country Club, a scenic and enjoyable course surrounded by classic Bluegrass State countryside.


In the afternoon, continue the Kentucky experience with a private immersive tour at Castle & Key Distillery. This beautiful distillery setting is a fantastic introduction to the region’s bourbon heritage, giving the group time to explore, taste and enjoy one of Kentucky’s most atmospheric distillery experiences.


Golf: Frankfort Country Club

Experience: Private immersive tour at Castle & Key Distillery

Overnight: The Manchester Hotel


Day 3 – Bluegrass Distillers & VIP Race Day at Keeneland

Begin the day with a private tour and tasting at Bluegrass Distillers, including a cocktail class where you will learn how to make a true Kentucky classic.


In the afternoon, it is time for one of the standout moments of the trip: Race Day at Keeneland Racecourse. This is far more than a standard race day. Your host, Robert Osbourn from Taylor Made Farm, will meet the group and guide you through a rare insider’s perspective of Kentucky horse racing.


From the paddock to the Winner’s Circle, you will enjoy a fully immersive VIP experience, complete with access to the dining clubhouse and an elegant lunch. Keeneland is one of the most prestigious racecourses in the United States, making this a brilliant addition to a luxury Kentucky golf holiday.


Please note that Keeneland clubhouse dress code guidelines apply.


Experience: Bluegrass Distillers private tour, tasting and cocktail class

Race Day: VIP Keeneland Racecourse experience with clubhouse lunch

Overnight: The Manchester Hotel


Day 4 – Golf at Greenbrier Country Club

Enjoy a more relaxed morning before heading out for afternoon golf at Greenbrier Country Club.


This is a great chance to enjoy another Kentucky golf course while keeping the pace of the trip comfortable. After your round, return to Lexington for an evening at leisure, with time to enjoy the bars, restaurants and relaxed Southern hospitality of the city.


Golf: Greenbrier Country Club

Overnight: The Manchester Hotel


Day 5 – Cherry Blossom Golf & Town Branch Distillery

Your final full day starts with morning golf at Cherry Blossom Golf & Country Club, a strong closing round for the tour and a fitting way to complete your Kentucky golf itinerary.


In the afternoon, visit Town Branch Distillery for a tour, tasting and fill-your-own-bottle experience. You will even be able to personalise your bottle with a handwritten label, giving you a great keepsake from your Kentucky golf and bourbon holiday.


Golf: Cherry Blossom Golf & Country Club

Experience: Town Branch Distillery tour, tasting and fill-your-own-bottle experience

Overnight: The Manchester Hotel


Day 6 – Check Out & Depart

After breakfast, check out of The Manchester Hotel and meet your private transfer for the journey back to the airport.


Return home after five nights of Kentucky golf, bourbon, racing and Southern hospitality.

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Time Zone:

GMT-4

Currency:

$ (US Dollar)

Temperature:

0°C – 31°C

Cost of a Beer:

£4

Cost of a 3-Course Meal:

£27

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