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

Icon Share

SHARE

Advisor - Arielle Heller
Curated By

Arielle Heller

  • City Travel

  • Food & Wine

  • Weekend Getaways

  • Bachelor Party Destinations

  • Kentucky

  • Local Food

Advisor - Barrels & Bros: The Ultimate Guys' Getaway on the Kentucky Bourbon Trail
Curator’s statement

This trip isn't just about tasting whiskey—it is about learning and discovering the spirit (literally) of Kentucky. From modern, design-forward distilleries to relaxed barrel tastings in a barn, you can experience every side of the bourbon world. Plus, you can enjoy one of the best meals of your lives at a distillery of all places (read on to find out). If you’re planning a guys' getaway that blends great food, history, and smooth sips, this is it.

The Fora Difference

Book with Arielle to access exclusive perks and experiences on your trip.

Icon Travel Perks
Killer perks

Free upgrades, spa credits and more—we got you

Icon Recommendations
Personalized recs

Customized travel planning for your style

Icon Inside Knowledge
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay

Unlock perks by contacting Arielle to book your trip.

Day 1: Warm-up in Whiskey City

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.

Advisor - Arielle Heller

A note from Arielle

Pro tip: NuLu is the local neighborhood to explore. It is full of solid pre- and post-dinner drink spots. Spend your evenings here.

Day 2: Bourbon Trail, round one (with Bourbon Boys)

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.

Day 3: Urban bourbon & baseball

Bar Vetti

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.

Day 4: Trail finale with Bourbon Boys

Inside Maker's Mark

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.

Need to know

Bring a bottle shipper – You’ll want to take home a few favorites.

Mix up the vibes – Make sure your selection of distilleries gives a perfect mix: old, new, rustic, refined.

Check local events – The city has a minor league stadium and arena nearby—great if you want to catch a game after dinner.

Walkable zones – Most nightlife and restaurants are clustered in NuLu. If staying at Distil, be ready for a few 10- to 15-minute walks.

Advisor - Arielle Heller

Travel Advisor

Arielle Heller

Get in touch with Arielle

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can expect a response from Arielle within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).

For more inspiration and insider recommendations, visit our Kentucky page.

We use cookies to enhance the user experience. Read our Privacy Policy here.