57 days in Kentucky Itinerary

Get out of town with these interesting Louisville side-trips: Radcliff (Kentucky September 11th Memorial & Saunders Springs Nature Preserve), Elizabethtown (Freeman Lake Park, Swope's Cars of Yesteryear Museum, &more) and Bardstown (Oscar Getz Museum of Whiskey History, Lux Row Distillers, &more). There's still lots to do: learn insider's secrets on a distillery tour, test your team's savvy at popular escape rooms, snap pictures at The Big Four Bridge, and try to win big at Churchill Downs.

To find photos, where to stay, traveler tips, and other tourist information, read our Louisville road trip planning website.

Rio de Janeiro, Brazil to Louisville is an approximately 16-hour flight. The time zone changes from Brasilia Standard Time (BRT) to Eastern Standard Time (EST), which is usually a -2 hour difference. Traveling from Rio de Janeiro in September, Louisville is little chillier at night with lows of 19°C. Wrap up your sightseeing on the 13th (Sun) to allow time to drive to Newport.

Get out of town with these interesting Newport side-trips: EarthJoy TreeHouse Adventures (in Brooksville) and Maysville (The Old Pogue Distillery & Kentucky Gateway Museum Center).

For more things to do, photos, other places to visit, and other tourist information, you can read our Newport driving holiday planner.

You can drive from Louisville to Newport in 2 hours. Alternatively, you can take a bus. In October in Newport, expect temperatures between 23°C during the day and 9°C at night. Finish your sightseeing early on the 16th (Wed) so you can drive to Lexington.

Explore Lexington's surroundings by going to Ark Encounter (in Williamstown), Frankfort (Old State Capitol, Buffalo Trace Distillery, &more) and Boone County Distilling Co. (in Independence). And it doesn't end there: immerse yourself in nature at Kentucky Horse Park, indulge your thirst for a good beer at West Sixth Brewing, experience rural life at Claiborne Farm, and sample the fine beverages at James E. Pepper Distillery.

Plan a trip to Lexington easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by car from Newport to Lexington takes 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 24°C, and evening lows to 11°C. Wrap up your sightseeing on the 28th (Mon) early enough to drive to Loretto.

On the 29th (Tue), learn about winemaking at Jesters Winery & Cafe, brush up on your knowledge of spirits at Limestone Branch Distillery, and then brush up on your knowledge of spirits at Maker's Mark.

To see photos, other places to visit, maps, and other tourist information, refer to the Loretto online itinerary planner.

Drive from Lexington to Loretto in 1.5 hours. In October, daily temperatures in Loretto can reach 23°C, while at night they dip to 9°C. Finish your sightseeing early on the 29th (Tue) so you can drive to Owensboro.

Explore Owensboro's surroundings by going to Everly Brothers Monument (in Central City), Trover Wellness Park (in Madisonville) and Henderson (gabbi's Boutique, Farmer and Frenchman Winery, &more).

To find where to stay, photos, ratings, and other tourist information, go to the Owensboro trip site.

The Route module can help you plan travel from Loretto to Owensboro. Due to the time zone difference, you'll gain 1 hour traveling from Loretto to Owensboro. Expect a daytime high around 25°C in October, and nighttime lows around 11°C. Finish your sightseeing early on the 3rd (Sun) so you can drive to Paducah.

Venture out of the city with trips to Ben E. Clement Mineral Museum (in Marion), Kuttawa Harbor Marina (in Kuttawa) and Mineral Mound Golf Course (in Eddyville).

To see where to stay, photos, traveler tips, and other tourist information, read our Paducah visit planner.

You can drive from Owensboro to Paducah in 2.5 hours. Expect a daytime high around 17°C in November, and nighttime lows around 3°C. Cap off your sightseeing on the 11th (Mon) early enough to go by car to Bowling Green.

Change things up with these side-trips from Bowling Green: Onyx Cave (in Cave City), Mammoth Cave National Park (Fat Man's Misery, Echo River, &more) and Diamond Caverns (in Park City).

To see more things to do, maps, photos, and more tourist information, you can read our Bowling Green road trip planning site.

Traveling by car from Paducah to Bowling Green takes 2.5 hours. Alternatively, you can take a bus. In November in Bowling Green, expect temperatures between 17°C during the day and 3°C at night. Finish your sightseeing early on the 20th (Wed) to allow enough time to travel back home.