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Row of Kentucky bourbon bottles in front of a brick wall

Kentucky Holidays


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Kentucky holidays are filled with an array of diverse experiences and sights. Whether it’s sipping bourbon on a distillery tour, exploring the great outdoors, listening to live bluegrass music or meeting the famed Thoroughbred horses, a holiday to Kentucky will not disappoint.

Characterful Louisville has bags of charm and is home to the Kentucky Derby and birthplace of Muhammad Ali. For a fun night out work your way along Louisville’s Urban Bourbon Trail. Over in elegant Lexington there’s an array of horse farms to visit – Lexington is the horse capital of the world! It also makes a great base for exploring the many bourbon distilleries.

Take in the pastoral scenery of Kentucky’s famous bluegrass hills or explore the remarkable Mammoth Cave National Park. Car enthusiasts will love the National Corvette Museum in Bowling Green or for something unique head to Shaker Village in Pleasant Hill.

Trailfinders offers a range of holidays to Kentucky and our travel consultants are a mine of information about what to see and do. Whether you want to explore Kentucky on a fly drive, guided group tour of the Deep South or combine Kentucky with a Chicago city break – they’re the perfect people to ask.
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OUR HOLIDAYS TO KENTUCKY

Nobody offers more ways to explore Kentucky and the Deep South than Trailfinders.

Here’s a snapshot of some of our most popular holidays to Kentucky. If you don’t see what you’re looking for, click on the link below them to see our complete range of holidays and tours in the destination.
Spirit of Kentucky & Tennessee
USA
Fly Drive Holiday
14 days / 13 nights

Follow the Bourbon Trail, listen to bluegrass and country music, visit the horse capital of the world and Muhammad Ali’s birthplace on this fascinating southern sojourn.

Guide Price: €1,799 pp

Guide Price: £1,525 pp

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Chicago To Nashville - Blues, Bourbon & Honky Tonks
USA
Fly Drive Holiday
12 days / 11 nights

Journey from sensational Chicago down to Kentucky’s bluegrass hills and bourbon trails, then onwards to Tennessee’s music, mountains and moonshine.

Guide Price: €1,979 pp

Guide Price: £1,635 pp

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Bluegrass, Bourbon & the Blues
Indiana
Fly Drive Holiday
14 days / 13 nights

From vibrant Cincinnati and charming Northern Kentucky to the music meccas of Owensboro, Memphis and Nashville, travel through this unique region of the south where the whiskey is sour, the rhythms are sweet and all y’all are welcome!

Guide Price: €2,315 pp

Guide Price: £1,955 pp

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OUR RECOMMENDED HOTELS IN KENTUCKY

We feature a great range of accommodation in Kentucky, with something to suit all budgets. Maybe you’re looking for a good value hotel that’s an ideal base for exploring Kentucky’s charms, or perhaps a stylish hotel in a great downtown location.

What you won’t find here are thousands of Kentucky hotels to wade through. We have done the hard work for you and selected the best places to stay and our travel consultants are on hand to help, often with first-hand experience.
The Campbell House Lexington, Curio Collection by Hilton
4 star

Kentucky

Once an equestrian farm, this charming hotel blends elegant farmhouse style with modern comforts.
Hyatt Regency Louisville
4 plus star

Kentucky

Situated in heart of downtown Louisville, this stylish hotel is within walking distance to many of the top attractions, making it an ideal base for a stay in this welcoming city.
Hotel Genevieve
4 star

Kentucky

Tucked away in Louisville’s hip East Market district, commonly known as NuLu, this colourful hotel is perfectly located for enjoying the area’s diverse bars, distilleries, art galleries and antique shops.
Hotel Distil, Autograph Collection
4 star

Kentucky

With a prestigious location on ‘Whiskey Row’, this refined hotel brings modern amenities to a beautiful historic building.
Holiday Inn Paducah Riverfront
3 star

Kentucky

Overlooking the Ohio River, this friendly hotel is a convenient base for the myriad artistic and cultural attractions of Paducah.
Embassy Suites by Hilton Cincinnati Rivercenter
3 plus star

Kentucky

Perched on the banks of the Ohio River, this all suite hotel is the perfect base for the attractions of Northern Kentucky.

Tales from the Trail

Top tips and travel inspiration from the Trailfinders team

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