Barrels & Bros: The Ultimate Guys' Getaway on the Kentucky Bourbon Trail

Check in: The Hotel Distil is centrally located and trendy. It has great energy and is walkable to just about everywhere.

Muhammad Ali Center: This museum is a must if you have time. Powerful and inspiring.

Angel’s Envy Distillery: It’s a great first stop with beautiful architecture. Book in advance!

Dinner at Nami: Located in the NuLu district, this modern Korean steakhouse had a vibey, energetic atmosphere. The cocktails are also very solid.

Kick off your first big day on the trail with Bourbon Boys, a tour company I’d absolutely recommend. Their drivers are professional, their vans are roomy and comfortable, and the experience is seamless from start to finish.

First stop: Woodford Reserve, a postcard-worthy distillery tucked into horse country. Then it is on to Buffalo Trace, a historic, sprawling property with bottles like Blanton’s available at below-retail prices. Finish the day with Whiskey Thief, an ultra-casual, back-to-the-barrel tasting in a barn where you can fill your own bottle straight from the source.

Dinner at Jeff Ruby’s Steakhouse ends the day with aged steaks.

Morning

Rabbit Hole Distillery: This is a crowd-pleaser. The tasting room overlooks the city. It's ideal for bourbon newbies and connoisseurs alike. Their design and story are also fascinating.

Louisville Slugger Museum: This museum is surprisingly fun and interactive. Take the tour to hold pro-level bats (great photo ops).

Lunch at Doc Crow’s: Wide-ranging menu and solid portions. Great for a quick, satisfying lunch between stops. Not a dinner spot, though.

Afternoon

Kentucky Peerless Distillery: Located right in town with a rich history (founded by a Jewish immigrant pre-Prohibition). A unique story and strong lineup. Their ryes are exceptional.

Evening

Pre-dinner drinks at Michter’s Fort Nelson Bar: The cocktails here are next-level—generous pours and super creative. The bar alone is worth a stop.

Dinner at Bar Vetti: Italian in NuLu with cozy vibes. The pasta hit the spot. If you’re winding down from a heavy bourbon day, this is a great place to do it.

Round two with Bourbon Boys takes you deeper into bourbon country. Again, they will nail the logistics: comfortable ride, well-paced day, and a personable guide who makes sure everything is set before dropping you off at each stop.

Maker’s Mark was first: a large-scale, beautifully rustic distillery where you get a behind-the-scenes look at their wax-dipping and custom label program. Then, the unexpected star of the trip: Lunch at Willett Bar. Run by a James Beard-nominated chef, it will be hands-down the best meal you have all week. Do not skip it.

Then, end with the Willett Distillery tour, where tastings are scattered throughout the tour itself—a refreshing twist compared to the usual sit-down format. Their guides are funny, the bourbon is flowing, and the experience is a great final tasting.

Wrap up the trip at La Bodeguita de Mima, a lively Cuban spot in NuLu with strong drinks and festive energy. This is a fan-favorite meal in Louisville and a great final meal to wrap up the trip.