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Overview
Experience the quintessential blend of sport and spirit in the heart of the Bluegrass region. This curated itinerary offers four nights of premium accommodation in downtown Lexington, three rounds of championship golf on diverse courses, and guided tours of Kentucky’s most celebrated distilleries. The package includes single-occupancy lodging at the Hilton Downtown Lexington, green fees with carts, distillery admissions, and private transportation to all scheduled golf and whiskey venues.
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Highlights
Itinerary
Accommodation: Hilton Lexington/Downtown
Hilton Lexington/Downtown serves as the premier base for this itinerary, offering a sophisticated retreat in the center of the city’s vibrant dining and entertainment district. Strategically located overlooking Triangle Park and connected via skywalk to Rupp Arena and the Lexington Convention Center, the property places guests moments away from the region’s best culinary experiences.
The hotel provides a polished, upscale environment designed for the modern traveler. Guest rooms feature contemporary design, spacious layouts, and signature bedding, ensuring a restorative night’s sleep after active days on the course. On-site amenities include a fitness center, an indoor pool, and a stylish lobby bar perfect for evening relaxation. Dining options highlight Kentucky-inspired cuisine with an extensive bourbon selection, allowing guests to begin their tasting experience without leaving the property. Its central location offers seamless access to Versailles, Bardstown, and Georgetown, making it the ideal hub for exploring Central Kentucky.
Logistics: Arrive in Lexington (LEX); transfer to hotel.
Upon arrival at Blue Grass Airport, proceed to the Hilton Lexington/Downtown. For groups arriving on the same flight, private shuttle arrangements can be coordinated. For individual arrivals, taxi and rideshare services provide efficient transfer to the hotel. Take the evening to settle in, explore the immediate downtown area, or enjoy a welcome drink at the hotel bar before the itinerary begins in earnest the following morning.
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Morning: Golf at The Woodford Club
Afternoon: Castle & Key Distillery
Overnight: Hilton Lexington/Downtown
Golf: The Woodford Club
Start the trip with a round at The Woodford Club, a hidden gem located in Versailles amidst the rolling landscapes of horse country. This 18-hole course emphasizes traditional parkland golf, featuring tree-lined fairways, natural creeks, and gentle elevation changes that demand strategic placement over raw power.
The layout is known for its excellent conditioning and welcoming atmosphere, offering a genuine small-town Kentucky golf experience. The back nine is particularly notable for its blend of charm and challenge, with subtly sloped greens that reward a thoughtful short game. Following the round, the clubhouse patio provides a relaxed setting for lunch before departing for the afternoon distillery tour.
Distillery: Castle & Key Distillery
Castle & Key Distillery is an architectural marvel and a testament to Kentucky’s bourbon heritage. Originally built in 1887 by Colonel E.H. Taylor Jr., the site was restored from ruin to reveal limestone castles, peristyles, and sunken gardens. It is widely considered one of the most beautiful distillery campuses in the world.
The visit includes a guided tour highlighting the property’s restoration and its modern small-batch production methods. Castle & Key produces acclaimed bourbons, gins, and vodkas, blending historic grandeur with innovative distilling techniques. Guests will enjoy a curated tasting experience that explores the nuance of their spirits, followed by time to walk the botanical gardens and springhouse grounds—a serene and photogenic conclusion to the day.
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Morning: Golf at Bardstown Country Club
Afternoon: Bardstown Bourbon Company
Overnight: Hilton Lexington/Downtown
Golf: Bardstown Country Club
Day three takes the group to Bardstown Country Club, a championship-style course characterized by wide fairways and rolling hills. The course offers a fun, player-friendly mix of holes where elevation changes create compelling sightlines and strategic challenges.
Water hazards and bunkering are placed thoughtfully to enhance playability without being overly punitive, making it an excellent venue for a traveling golf group. The greens are consistently smooth, and the lush fairways highlight the natural beauty of the region. This round offers a memorable experience that pairs seamlessly with the afternoon’s premium bourbon excursion.
Distillery: Bardstown Bourbon Company
In stark contrast to the historic ruins of the previous day, Bardstown Bourbon Company represents the modern face of the industry. The facility features a striking glass-and-steel design and an open production model that allows visitors to view cutting-edge stills and blending labs.
The tour focuses on their collaborative and experimental approach to whiskey making. The tasting experience is elevated and educational, often featuring limited-edition expressions. Afterward, guests can enjoy the on-site restaurant, which is highly regarded for its craft cocktails and sophisticated menu designed to complement the spirits. The atmosphere is sleek and upscale, providing a gourmet counterpoint to traditional heritage distilleries.
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Morning: Golf at Cherry Blossom Golf Club
Afternoon: Dark Arts Whiskey House & Barrel House Distilling Co.
Logistics: Depart or Overnight as needed
Golf: Cherry Blossom Golf Club
The final round is played at Cherry Blossom Golf Club in Georgetown. Designed by Clyde Johnston, this course is frequently ranked among the best public layouts in central Kentucky. It features generous landing areas and distinctive bunkering, offering a bold and sculpted aesthetic different from the previous days.
Water hazards appear throughout the routing, rewarding confident decision-making, while the finishing stretch includes risk-reward par-5s and picturesque par-3s. The course is known for its smooth pace of play and polished conditions, ensuring a high-quality conclusion to the golf portion of the trip.
Distilleries: Dark Arts Whiskey House & Barrel House Distilling
The itinerary concludes with a dual visit to two of Lexington’s most intriguing craft producers. First, Dark Arts Whiskey House offers a moody, immersive aesthetic focused on bold, unconventional blending and finishing techniques. The experience here is intimate and storytelling-driven.
Just a short distance away in Lexington’s historic Distillery District, Barrel House Distilling provides a return to local roots. Visitors will explore a more hands-on, boutique operation that produces favorites like RockCastle Bourbon and Pure Blue Vodka. Together, these stops offer a deep dive into the emerging craft scene, providing a flavorful and authentic end to the journey.
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Logistics: Checkout and departure.
Check out of the Hilton Lexington/Downtown and proceed to the airport or your next destination.
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Includes / Excludes
Includes
- Four nights’ accommodation at Hilton Lexington/Downtown (single occupancy)
- Three rounds of golf at top regional courses, including cart fees
- Guided distillery tours with tastings at premier Kentucky bourbon venues
- Private transportation to all scheduled golf courses and distilleries
- Daily breakfast at the hotel
- All taxes and resort fees
Excludes
- Airfare to and from Lexington
- Airport transfers (unless otherwise arranged)
- Meals and drinks not specified in the itinerary
- Personal expenses and incidentals
- Additional rounds of golf or unscheduled tours
- Caddie and gratuity fees
Frequently Asked Questions
The selected courses are suitable for a range of skill levels, from experienced golfers to intermediate players. Each course offers a mix of challenge and playability to ensure all participants enjoy their rounds.
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Tours are typically group-based with expert guides, though private tours can be arranged upon request for an additional fee and with advance notice.
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Yes, private transportation is included for all scheduled itinerary activities, ensuring seamless travel between the hotel, golf courses, and distilleries.
