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Kentucky Race Season Golf Holiday

9 Nights + 5 Rounds

Enjoy a luxury Kentucky golf holiday with a proper American twist, combining five rounds of golf, boutique accommodation, bourbon country experiences and a standout race day at Keeneland Racecourse. Designed for a small group of 8 golfers, this 10-day Kentucky Race Season tour is based in Lexington at The Manchester Hotel, giving you a stylish base in the heart of the Bluegrass State.

This USA golf holiday is ideal for UK golfers who want more than a standard golf resort break. You will play Frankfort Country Club, Greenbrier Country Club, Cherry Blossom Golf & Country Club, Houston Oaks Golf Club and The Woodford Club, with private chauffeured transport throughout the itinerary. Away from the fairways, enjoy a behind-the-scenes tour at Castle & Key Distillery, a cocktail class at Bluegrass Distillers, a fully immersive private tour day with three stops and lunch, plus an unforgettable VIP race day experience at Keeneland Racecourse.

Available during April 2027 race season dates, this is a brilliant choice for golfers looking for a small group golf trip to America that blends golf, bourbon, horse racing, great food and Southern hospitality.

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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 5 out of 5

Houston Oaks Country Club & Retreat

Set in Hockley, a short drive north west of downtown Houston, Houston Oaks Country Club & Retreat is a private golf, sporting and lifestyle club spread across nearly 1,000 acres of Texas countryside. It has a proper retreat feel, combining championship golf with lodging, dining, outdoor activities and relaxed rural scenery, making it a strong option for golfers looking to experience Texas beyond the city. The golf offering includes 27 holes, led by an 18-hole championship course designed by Chet Williams. The main course has six sets of tees, helping it work for a wide range of abilities, from newer golfers through to low-handicap players. It is a private club environment, so access needs to be planned carefully through membership, hosted guest play or approved stays. Houston Oaks is especially appealing because the wider property feels more like a countryside resort than a standard golf club. Alongside golf, the club highlights fishing, equestrian facilities, shooting sports, tennis, wellness, wine experiences and social spaces, giving non-golfers and mixed groups plenty to do during a stay. Accommodation is also part of the appeal, with lodging options ranging from cottages and hotel-style rooms to upscale estate homes. The official lodging information describes spacious living areas, kitchens and private settings designed for families, groups, corporate retreats and longer stays. For UK golfers, Houston Oaks works best as part of a wider Texas itinerary, combining golf with Houston, ranch-style experiences, barbecue, live music, shopping, sports and possible extensions to Austin, San Antonio or the Gulf Coast.
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

The Woodford Club

Located in Versailles, in the heart of Kentucky’s Bluegrass Region, The Woodford Club is a semi-private golf and country club with a relaxed, scenic setting close to Lexington. The club’s 18-hole, par-71 course is set across 150 acres of rolling hills, with zoysia fairways, strong putting surfaces and horse-country views that give the round a real Kentucky feel. The course is a good fit for visiting golfers who want something playable, friendly and full of local character. It is not just a flat resort-style layout; the rolling terrain, mature trees, doglegs, water carries and elevated shots mean golfers need to think carefully about positioning and approach play. The club highlights individual holes with a mix of strategic par 4s, inviting par 5s, elevated greens and water-protected par 3s, giving the round plenty of variety. Facilities include a synthetic turf driving range, golf programming and a clubhouse setting that works well after the round. The Jack Jouett Restaurant & Tavern adds a strong social element, with multiple dining spaces, outdoor patio areas and a bourbon-focused tavern featuring more than 50 bourbons — very on-brand for Woodford County. For UK golfers, The Woodford Club works particularly well as part of a Kentucky golf and bourbon itinerary. It sits close to historic Versailles, Keeneland Race Course and a wide choice of distilleries, making it easy to combine golf with horse country, bourbon tastings, Southern food and Bluegrass scenery. The club also notes that it is around 12 minutes from Blue Grass Airport, which makes arrival logistics refreshingly simple.
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 in Kentucky, where airport transfers are provided by The Manchester Hotel.


Check in to The Manchester Hotel in Lexington and settle into your base for the trip. The hotel provides a stylish introduction to Kentucky, with warm interiors, excellent food and drink options and a great location for exploring the city.


A suggested dinner option is Granddam at The Manchester, a Michelin One Key recipient and a great way to start your Kentucky golf and bourbon holiday.


Overnight: The Manchester Hotel


Day 2 – Frankfort Country Club & Castle & Key Distillery

Start the trip with morning golf at Frankfort Country Club, your first taste of golf in Kentucky’s Bluegrass region.


In the afternoon, enjoy a private behind-the-scenes tour at the historic Castle & Key Distillery. Set in one of Kentucky’s most atmospheric distillery locations, this experience is a brilliant introduction to bourbon country and the heritage that makes this region so special.


Golf: Frankfort Country Club

Experience: Private behind-the-scenes tour at Castle & Key Distillery

Overnight: The Manchester Hotel


Day 3 – Greenbrier Country Club

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


This is a great day to settle into the pace of the trip, with time to enjoy Lexington before another enjoyable round in Kentucky. After golf, return to The Manchester Hotel for an evening at leisure.


Golf: Greenbrier Country Club

Overnight: The Manchester Hotel


Day 4 – VIP Race Day at Keeneland Racecourse

Today is one of the standout experiences of the trip: Race Day at Keeneland Racecourse.


You will experience prestigious Keeneland Racecourse for live racing as if your very own horse was running. Your host, Robert Osbourn from Taylor Made Farm, a worldwide leader in thoroughbred sales and marketing, 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, this is a fully immersive VIP race day experience, with access to the dining clubhouse and an elegant lunch included. Keeneland is one of the most iconic venues in American horse racing, making this a truly memorable addition to your Kentucky golf holiday.


Please note that Keeneland clubhouse dress code guidelines apply.


Experience: VIP Keeneland Racecourse race day with clubhouse dining

Overnight: The Manchester Hotel


Day 5 – Cherry Blossom Golf & Bluegrass Distillers

Start the day with morning golf at Cherry Blossom Golf & Country Club, a strong addition to the golf itinerary and a great contrast to the earlier rounds.


In the afternoon, visit Bluegrass Distillers for a cocktail class, where you will learn how to make a true Kentucky classic from the experts. It is a relaxed and fun way to enjoy the region’s bourbon culture after golf.


Golf: Cherry Blossom Golf & Country Club

Experience: Cocktail class at Bluegrass Distillers

Overnight: The Manchester Hotel


Day 6 – Houston Oaks Golf Club

Enjoy morning golf at Houston Oaks Golf Club, another excellent Kentucky course and a great mid-trip round for the group.


After golf, the rest of the day is free to enjoy Lexington, unwind at the hotel or head out for food and drinks in the city.


Golf: Houston Oaks Golf Club

Overnight: The Manchester Hotel


Day 7 – Private Tour Day

Take a break from the fairways and enjoy a fully immersive private tour day with your own driver.


The day includes three stops and experiences, with lunch included. This is a brilliant opportunity to explore more of Kentucky’s Bluegrass region, whether the focus is bourbon, local culture, horse country or a mix of carefully selected experiences.


Experience: Private tour day with three stops, experiences and lunch

Overnight: The Manchester Hotel


Day 8 – Free Day in Lexington

Today is yours to enjoy at leisure.


Relax at The Manchester Hotel, explore Lexington, enjoy the local bars and restaurants, or add on extra experiences. Optional additions could include more golf, another bourbon tasting, horse country experiences or local sightseeing.


Day at leisure: Optional add-ons available

Overnight: The Manchester Hotel


Day 9 – The Woodford Club

Enjoy your final round of the trip at The Woodford Club, a memorable Kentucky golf course surrounded by classic Bluegrass scenery and horse country.


This is a fitting final round before returning to Lexington for your last evening at The Manchester Hotel.


Golf: The Woodford Club

Overnight: The Manchester Hotel


Day 10 – Check Out & Depart

Check out of The Manchester Hotel and transfer back to the airport.


Return home after 10 days 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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