Louisville Travel Guide

Louisville is bourbon country, and our homes put you minutes from Whiskey Row, the Highlands and Churchill Downs. This Louisville travel guide collects the tips we give our own guests. These are the places we go ourselves.

Louisville is the starting point for the Kentucky Bourbon Trail, and you don’t have to leave the city to tour a working distillery. Whiskey Row, along West Main Street downtown, has Old Forester, Michter’s Fort Nelson, and several more within a few blocks. Book tours ahead on weekends.

Our Favorite Bourbon Bars

• Neat Bourbon Bar & Bottle Shop (Highlands): the best whiskey list in Louisville, with a bottle shop attached. Small room, so go early.
• The Bar at Fort Nelson (Whiskey Row): Michter’s upstairs bar and the best cocktail program in the city. Reserve.
• Haymarket Whiskey Bar (East Market): hundreds of whiskeys, bourbon on tap, and zero pretension.
• Trouble Bar (Shelby Park): the best place to learn bourbon, with thoughtfully built flights.
• Watch Hill Proper (Prospect): worth the drive when you’re celebrating. Book the tasting.

Our Favorite Places to Eat

• North of Bourbon (Germantown): New Orleans food and a strong bourbon program. Reserve.
• The Silver Dollar (Frankfort Ave): honky-tonk, fried chicken, and an outstanding whiskey list.
• Merle’s Whiskey Kitchen (Whiskey Row): fried chicken and live music, right across from Old Forester.
• Repeal Oak Fired Steakhouse (Whiskey Row): the nice-dinner pick, with a bourbon list to match.

In the Highlands

Bardstown Road is Louisville’s most walkable stretch of bars, restaurants, and shops. Start with coffee at Safai Coffee, have a Belgian beer inside a restored church at Holy Grale, and finish at Neat.

Day Trips

Buffalo Trace (about an hour, free tours), Woodford Reserve (through Bluegrass horse country), and Maker’s Mark (hand-dip your own bottle in red wax). Reserve ahead.

Big Event Weekends

• Kentucky Derby: the first Saturday in May at Churchill Downs. See our Kentucky Derby rentals.
• Louder Than Life and Bourbon & Beyond: see our Louisville festival rentals.
• AAU tournaments and Expo Center events: see rentals near Kentucky Expo Center.

Louisville Travel Guide: When to Visit

Spring and fall are the best times to visit. The Kentucky Derby runs the first Saturday in May, and the big bourbon and music festivals fill the city in September. Book early for both. Summer is hot and humid, and winter is quiet, which makes it a good time for distillery tours without the crowds.

Getting Here

Louisville Muhammad Ali International Airport (SDF) is only a few miles from our Louisville homes, so you can land and be at the house fast. Downtown, Whiskey Row and the Highlands are all a short drive or rideshare away. Every stop in this Louisville travel guide is within easy reach of our homes.

Where to Stay

The Bonnycastle is a historic 6-bedroom home in the Highlands, and Parkside Retreat is a 5-bedroom home with a heated pool. Compare both on our Louisville large group rentals page. Both homes are built for groups of 6 to 15, and booking direct on our site means no platform fees. Tell us your dates and group size, and we will help you pick the right home for your trip.

Heading to Florida too? See our Anna Maria Island and Bradenton travel guide, or browse all of our travel guides.