Some bourbon trips are built around careful planning.

This was not entirely one of those trips.

To be fair, there was planning involved. Scott and I knew some of the places we wanted to hit. We had a few tours booked, a few targets in mind, and a general sense that we wanted to make the most of the week. But part of the fun of a trip like this is leaving enough room for the unexpected.

And on this trip, the unexpected did a lot of heavy lifting.

Technically, the trip started before we ever crossed fully into Kentucky. After I arrived in Tennessee, Scott and I made our way to Jack Daniel’s and Chattanooga Whiskey, along with a few other stops on the Tennessee Whiskey Trail. That included a return visit to Far Better, which was sadly out of the cask strength bourbon that won my shelf challenge earlier this year.

With the chance to buy any one of endless great bourbons, I chose to bottle my own “almost tequila” agave whiskey.

There was also Nashville Barrel Company, where I sampled a barrel-proof agave spirit. It is basically tequila they cannot call tequila because it is not made in Mexico. Whatever they are allowed to call it, I liked it enough to bring a bottle home.

But for this “best of the trip” recap, I’m going to start with the Kentucky run.

On Tuesday, we drove up and did the Stateline Whiskey Tour: Old Glory in Clarksville, Tennessee; MB Roland in Pembroke, Kentucky; and Casey Jones in Hopkinsville, Kentucky.

It is three distilleries, two states and just enough driving between stops to make it feel like a real trail without spending the whole day in the car.

At Old Glory and MB Roland, we stuck mostly with tastings. Old Glory had a solid single barrel pick that came home with me, and MB Roland added another agave bottle to the haul. Those were good stops, but Casey Jones ended up being the highlight of the day.

We got a cool tour there, and I left with two bottles: a Revere Single Barrel and an amburana-finished whiskey that is basically barrel-aged moonshine. Both were pour-your-own picks, and both bottles were signed by me and master distiller AJ.

That is the kind of souvenir that feels a little more personal than just grabbing something from a shelf.

Then came the lowlight of the day.

We headed to Owensboro and checked into a Motel 6 that did its absolute best to embody the phrase “roach motel.” I think there was more dirt inside the room than outside it. I could not check out of there fast enough.

Thankfully, Wednesday made up for it.

A vintage marketing race car at Green River Distillery.

We got a little bit of a late start heading to Green River, but our tour guide, Josh, took great care of us. Scott and I were the only two on the tour, and he gave us a thorough behind-the-scenes look at Green River’s history and what the distillery is doing now.

The thing that stood out to me most was how connected Green River is to the surrounding community. It does not feel like a tourist attraction that happens to be located in Owensboro. It feels like part of Owensboro itself.

I already loved their whiskeys, but the visit gave me even more appreciation for the place behind them.

More on Green River later.

From there, we hoofed it over to the Jim Beam Distillery in Clermont, where we found the first major bottle surprise of the trip: Old Grand-Dad 114 Single Barrel.

Scott and I had both been hunting that bottle for weeks. This was the first time either of us had seen it in person, let alone at MSRP. I think we both got our bottles for about $50. The folks at Beam told us it sells out almost as soon as it arrives, so if we had shown up the week before or the week after, we probably would have missed it.

That alone would have made the stop worthwhile, but the tour was even better.

We did the Maturation Matters tour, and even though our delay at Green River caused us to miss our original time, Beam had another tour available. Our guide, Drake, was an amazing source of information.

The highlight was going inside one of Beam’s rickhouses and thieving bourbon from three different barrels: one from the top, one from the middle and one from the bottom of the warehouse.

All three pours were excellent, but the real value was getting to experience how barrel location affects maturation. It was also a reminder that there are some Beam products neither Scott nor I drink as regularly as we probably should.

That may change after this trip.

Thursday was another tour-heavy day, and after a night at the Motel 6 in Shepherdsville, we were ready for whiskey.

The Shepherdsville Motel 6, by the way, was only about 500 percent cleaner than the previous hotel. Bigger room. Clean. Refrigerator. Microwave. The only real drawback was the lighting. The room was on the dark side, but compared to the Owensboro dirt sanctuary, it felt like luxury lodging.

Scott stands in the aisle on the bottom floor of the second-oldest rickhouse at Wild Turkey.

We started the day at Wild Turkey, where we toured the grounds with a guide named Bo. Bo seemed to know the entire history of everything, including plenty about the legendary Jimmy Russell. He also seemed to have a decent working relationship with Jimmy, which gave the tour some extra weight.

We visited one of the oldest rickhouses on the property, built just after 1900, and also saw the building that housed Jimmy Russell’s original office. It was a great look into the story behind one of so many people’s favorite bourbons.

Wild Turkey is one of those brands that feels familiar even before you visit, but being there gives the place a little more soul.

From there, we went to Heaven Hill, where we had a tasting of their six grain-to-glass whiskeys.

All six were good. Really good. But Scott and I both agreed that the chinkapin oak wheated bourbon was the best of the bunch. Sadly, everyone else apparently agreed with us, because it was no longer available in the shop.

That one hurt a little.

We had lunch at Heaven Hill, then made our way to Willett for a flight of their finest. Willett has a very different feel from some of the bigger distilleries — smaller, more curated, and maybe just a little more mysterious. The pours matched the setting.

After that, we drove down to Wilderness Trail and got there just before closing. Our host still poured us samples of some of their best and gave us a short background on the distillery before we headed out.

That visit was way too short, but it was enough to put Wilderness Trail on the list for next time. Some places you visit and check off the list. Others you visit just long enough to realize you need to come back.

Wilderness Trail is definitely in the second category.

Then it was back to the hotel, where the room was still dark, but clean — and after the night before, clean was doing a lot of heavy lifting.

Three days in, we had already found bottles we did not expect, tasted whiskey straight from the barrel, toured rickhouses, met great guides and collected more memories than I could reasonably fit into one post.

And somehow, the best moments of the trip were still ahead.