Holiday Overview
Explore Kentucky
Explore the best of Kenctucky with everything from world-class horse racing and the best bourbon to flavourful culinary stops and deep-rooted history, the list of things to do in Kentucky seems almost endless. Whether your ideal holiday is relaxing on an old steamboat on the Ohio River, hiking in a breathtaking gorge or experiencing small-town charm, every adventure in the Bluegrass State is sure to leave you wanting more.
Explore Kentucky includes:
- International Flights
- Car Hire
- 7 Nights Accommodation (sample accommodation can be changed to suit requirements)
Day 1 - Cincinnati Arrival – Newport/Covington
Arrive at Cincinnati Airport, pick up your rental car and make the short drive to your hotel in the Covington/Newport area. Explore the Northern Kentucky area in Newport and Covington. Enjoy an afternoon on the Levee, a popular dining and entertainment complex or a cruise with BB Riverboats to take in the city views of Covington and Newport from the river. Schedule a walking tour with Riverside Food & Culture Tours. Check out the B-Line, northern Kentucky's bourbon experience with distilleries, bourbon bars and bourbon-centric restaurants.
Featured accommodation
Aloft Newport on the Levee
Day 2 - Newport/Covington – Lexington
On the way to Lexington, the Horse Capital of the World, stop in Georgetown at Old Friends Farm, a Thoroughbred retirement home to meet and greet retired racehorses, or Toyota Motor Manufacturing Kentucky, America's first and the world's largest Toyota manufacturing facility. See a horse show or demonstration at the Kentucky Horse Park, take a tour of the historic Keeneland Racecourse and book a horse farm tour with Horse Country. In the evening, check out Lexington's Distillery District or the new dynamic public marketplace, Greyline Station.
Featured accommodation
Hilton Lexington Downtown
Day 3 - Lexington – Red River Gorge – Berea
Enjoy an amazing outdoor adventure in Red River Gorge Geological Area. Zip through the trees at Boone Creek Outdoors or venture below-ground for a clear-bottom kayak tour of a flooded mine at the Gorge Underground. Hike or take the sky lift at Natural Bridge State Resort Park to see the sandstone arch. Music lovers may want to head even farther east to check out U.S. 23 Country Music Highway and history buffs may want to check out sites from the famous Hatfield-McCoy feud around Pikeville. End the day in Berea, the Folk Arts & Crafts Capital of Kentucky. Pick up handcrafted treasures at the Kentucky Artisan Centre at Berea or the many local shops in town. Be sure to try the spoonbread at the Historic Boone Tavern Hotel and Restaurant. Returning to Lexington for your overnight stay.
Featured accommodation
Hilton Lexington Downtown
Day 4 - Lexington – Cumberland Falls – Mammoth Cave National Park – Bowling Green
Head south to Mt. Vernon to the Kentucky Music Hall of Fame and Museum. Continue to Corbin to see Kentucky's most breathtaking waterfall at Cumberland Falls State Resort Park. If time allows, stop in the Harlan Sanders Cafe and Museum or along Lake Cumberland, the Houseboat Capital of the World. Take a tour at Mammoth Cave National Park, the world's longest- known cave system. Continue onto Bowling Green and check out the National Corvette Museum and NCM Motorsports Park. In the evening, take a walk around downtown and Fountain Square.
Featured accommodation
Baymont by Wyndham Bowling Green
Day 5 - Bowling Green – Land Between the Lakes – Paducah
Depart for Land Between the Lakes National Recreation Area (LBL). Stop in Hopkinsville at Casey Jones Distillery for a sip of bourbon or moonshine. At LBL, visit the Gold Pond Planetarium or drive through the Elk & Bison Prairie. Enjoy a meal at Patti's 1880's Settlement before heading to Paducah, an UNESCO City of Crafts and Folk Arts. See amazing works of art at the National Quilt Museum and then walk along the city's floodwall murals.
Featured accommodation
La Quinta Inn & Suites by Wyndham Paducah
Day 6 - Paducah – Owensboro
Mosey over to Owensboro for barbecue and bluegrass music. Downtown, the Bluegrass Music Hall of Fame and Museum celebrates and preserves the history of bluegrass music. Sample bourbon at Green River Distilling Co., the westernmost point on the Kentucky Bourbon Trail. There's also the Owensboro Museum of Fine Art and the Western Kentucky Botanical Garden. Stroll along the riverfront or splash into some fun at Smothers Park. Take in a seasonal event at the Riverpark Centre. Visit Reid's Orchard for fresh produce and baked goods.
Featured accommodation
Hampton Inn and Suites Downtown Owensboro Waterfront
Day 7 - Owensboro – Louisville
Depart for Louisville, Kentucky's largest city. Explore by taking a tour at the Kentucky Derby Museum or enjoying seasonal racing at Churchill Downs, home of the Kentucky Derby. Have a lunch cruise aboard the Belle of Louisville while viewing the city from the water. Check out the downtown museums and attractions on Whiskey Row, including the Muhammad Ali Centre, the Louisville Slugger Museum & Factory, the Frazier History Museum, the Evan Williams Bourbon Experience and more.
Featured accommodation
Galt House Hotel Louisville
Day 8 - Louisville – Cincinnati Departure
This morning drive to Cincinnati and return your car in time for your departure flight.
Aloft Newport on the Levee
The Aloft Newport on the Levee is located across the river from downtown Cincinnati. In the perfect located in the entertainment district with nearby attractions including Great American Ball Park. The hotel is modern and offers guests a comfortable stay.
Hilton Lexington Downtown
Hilton Lexington Downtown is a modern hotel welcoming guests to enjoy a comfortable stay in their stylish rooms. Located in downtown Lexington it is in the perfect location to explore the local area.
Baymont by Wyndham Bowling Green
Baymont Inn by Wyndham Bowling Green welcomes guests with Southern Hospitality in their comfortable hotel rooms. Located nearby Western Kentucky University, Sloan Convention Centre and the National Corvette Museum in Kentucky. The Jack Daniels Distillery and the Grand Ole Opry are also nearby in Tennessee.
La Quinta Inn & Suites by Wyndham Paducah
La Quinta Inn & Suites by Wyndham is a contemporary hotel with lots of great amenities. Located in a fantastic area with easy to access to popular attractions.
Image Gallery
Purple Bridge, Newport
Bluegrass Music Hall, Owensboro
BB Riverboats
Newport
Horses in Lexington
Bluegrass Music Hall, Owensboro
Bowling Green
National Corvette Museum
Cumberland Falls
Bell Hooks Mural, Berea
Kayaking in Berea
Pinnacles Walking Trail, Berea
Lost River Cave, Bowling Green
Ariel View of Owensboro
Alternative My Canada Trips Holidays That May Interest You
Below you will find a small selection of 2024, 2025 My Canada Trips holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 021 7732 and let one of our Canada Holiday experts design the perfect trip for you
USA Road Trips
Pacific Coast Highway Road Trip
- 7 Nights
- Los Angeles
- Pismo Beach
- Monterey / Carmel
- Yosemite National Park
- San Francisco
USA Road Trips
Canyon Adventure Fly Drive Holiday
- 7 Nights
- Las Vegas
- Bryce Canyon
- Moab
- Mesa Verde
- Grand Canyon
USA Fly Drive Holidays
California Fly Drive
- 11 Nights
- San Francisco
- Sonoma
- Lake Tahoe
- Yosemite National Park
- Death Valley
- Los Angeles
- San Diego
USA Road Trips
Blues & Booze USA Road Trip
- 12 Nights
- Chicago
- Indianapolis
- Louisville
- Nashville
- Memphis
- Vicksburg
- New Orleans
USA Fly Drive Holidays
The Wild West Fly Drive Holiday
- 15 Nights
- Denver
- Cheyenne
- Rapid City
- Cody
- Jackson
- Salt Lake City
- Moab
- Durango
- Colorado Springs
USA Fly Drive Holidays
Best of New England Fly Drive
- 14 Nights
- Boston
- Portland Maine
- Bar Harbor
- White Mountains
- Killington
- The Berkshires
- Mystic
- Yarmouth MA
USA Self Drive Holidays
Talkin' Texan Self Drive Holiday
- 12 Nights
- Dallas
- Austin
- Fredericksburg
- Bandera
- San Antonio
- Corpus Christi
- Houston
USA Road Trips
Boston to New York By The Beaches Road Trip
- 8 Nights
- Boston
- Yarmouth
- Martha's Vineyard
- Mystic
- Riverhead
- The Hamptons
- New York
USA Self Drive Holidays
The Classic West Self Drive Holiday
- 13 Nights
- Los Angeles
- Laughlin
- Grand Canyon
- Kayenta
- Lake Powell
- Bryce Canyon
- Las Vegas
- Death Valley
- Yosemite National Park
- Lake Tahoe
- San Francisco
USA Fly Drive Holidays
Route 66 Fly Drive Holiday
- 15 Nights
- Chicago
- St Louis
- Springfield
- Oklahoma City
- Amarillo
- Albuquerque
- Holbrook
- Williams
- Las Vegas
- Los Angeles
USA Fly Drive Holidays
Western Trails
- 14 Nights
- Salt Lake City
- Lava Hot Springs
- Boise
- McCall
- Coeur d’Alene
- Whitefish
- Helena
- Yellowstone
- Jackson Hole
- Casper
- Cheyenne
- Denver
USA Fly Drive Holidays
Legends and Landscapes of the Old West
- 13 Nights
- Denver
- Cheyenne
- Deadwood
- Minneapolis
- Badlands
- Fargo
- Bismarck
- Medora
- Casper
- Buffalo WY
USA Fly Drive Holidays
Best of the Great American West
- 20 Nights
- Rapid City
- Deadwood
- Medora
- Sheridan
- Billings
- Helena
- Whitefish
- Butte
- Yellowstone
- Cody
- Riverton
- Jackson
- Ketchum
- McCall
- Boise
USA Fly Drive Holidays
Giant Trees and Ancient Forests Road Trip
- 5 Nights
- San Francisco
- Chester, CA
- Lake Tahoe
- Oakhurst
USA Fly Drive Holidays
Explore Kentucky
- 7 Nights
- Newport, KT
- Lexington
- Bowling Green
- Paducah
- Owensboro
- Louisville
USA Self Drive Holidays
Best of Florida Self Drive Holiday
- 9 Nights
- Orlando
- Clearwater
- Naples
- Miami
USA Road Trips
Coasts and Mountains of the South Road Trip
- 7 Nights
- Atlanta
- Asheville
- Charlotte
- Myrtle Beach
- Charleston
- Savannah
USA Road Trips
Wild Wild West USA Road Trip
- 12 Nights
- Los Angeles
- San Diego
- Tucson
- Las Cruces
- Santa Fe
- Durango
- Kayenta
- Williams
- Las Vegas
USA Fly Drive Holidays
The Florida Keys Fly Drive Holiday
- 7 Nights
- Miami
- Islamorada
- Key West
- Key Largo
USA Self Drive Holidays
Volcanic Peaks to Sparkling Shores Self Drive
- 9 Nights
- Portland
- Astoria
- Port Angeles
- Seattle
- Ashford
- Welches
- Grants Pass
- Coos Bay
USA Road Trips
Historic Cities of the Mid-Atlantic Road Trip
- 11 Nights
- Washington DC
- Baltimore
- Philadelphia
- Gettysburg
- Luray
Canada Fly Drive Holidays
Quebec to New England Adventure
- 14 Nights
- Montreal
- Stowe
- White Mountains
- Bar Harbour
- Ogunquit
- Boston
- Green Mountain National Forest
USA Fly Drive Holidays
Great North Music Tour Fly Drive
- 12 Nights
- Chicago
- Detroit
- Cleveland
- Pittsburgh
- Philadelphia
- New York
- Boston
USA Fly Drive Holidays
Route 66 Best of the West
- 14 Nights
- Los Angeles
- Palm Springs
- Kingman
- Williams
- Holbrook
- Santa Fe
- Chicago
USA Fly Drive Holidays
San Antonio & Texas Hill Country
- 9 Nights
- San Antonio River Walk
- San Antonio Hill Country
- Bandera Dude Ranch
- San Antonio
USA Fly Drive Holidays
Utah's Red Rocks and Canyons
- 12 Nights
- Las Vegas
- Zion National Park
- Bryce Canyon
- Torrey
- Moab
- Kanab
USA Self Drive Holidays
Northwest Inn-Sider Self Drive Holiday
- 13 Nights
- Friday Harbor
- Whidbey Island
- Port Townsend
- Cannon Beach
- Portland
- Eugene
- Ashland
- Eureka
- Sonoma
USA Road Trips
Mountains and Canyons Fly-Drive
- 14 Nights
- Denver
- Glenwood Springs
- Moab
- Kayenta
- Page
- Williams
- Las Vegas
USA Fly Drive Holidays
Wonders of Alaska Fly Drive Holiday
- 7 Nights
- Anchorage
- Seward
- Talkeenta
- Denali National Park
Canada Fly Drive Holidays
Eastern Canada and New England Discovery
- 15 Nights
- Toronto
- Ottawa
- Montreal
- Quebec City
- Boston
- New York
- Washington DC
- Niagara Falls