There's a reason that bourbon is historically produced in Kentucky (even though legally it can come from anywhere in the US): the limestone filtered water and locally-grown grains just plain taste better, and the fact that the region has, for most of history, made most of America's bourbon, means that the people there have a deep passion for it, and they also have old-school, time-tested recipes, too. Whether you're a bourbon snob, or you just like drinking, the Kentucky Bourbon Trail is a must-visit.
Starting off in Louisville, visit the Evan Williams Bourbon Experience. They give a really thorough background on the drink and Louisville's history with it (and yes, it ends with a tasting). Seeing as this is the only "bourbon tour" in Louisville proper, it's worth the stop. The samples were pretty small, but it's straight bourbon, so you're probably gonna feel pretty good afterward. Grab a bottle or some bourbon balls in the gift shop afterwards!
Next up is the Buffalo Trace Distillery. It's not a part of the Kentucky Distillers Association's official Bourbon Trail, but they are, however, open for tours and tastings. They have a few iconic bourbon brands that are produced here: Buffalo Trace, Blanton's (with the little horse on top of the round bottle), and Eagle Rare. If you've got a sweet tooth, definitely also try the bourbon cream (it's perfect if you're still not sold on straight bourbon) and bourbon brittle.
Next, hit up Wild Turkey Distillery, which has been crafting Kentucky bourbon since 1869. They offer both tours and tastings individually, so if you'd rather skip seeing the still and warehouse, you can just sample their wares-- try the sweet and spicy Wild Turkey Honey Stinger!
When you're ready for a hearty meal, there's super delicious BBQ right off I-75 at Red State BBQ. This is a great bit of Texas BBQ in the heart of Kentucky. The brisket is renowned, especially with their Texas hot sauce. They have a good beer selection, excellent pulled pork, tasty baked beans and a variety of BBQ sauces.
Once you get to Shepherdsville, visit the Jim Beam Distillery. Since it's the largest maker of Kentucky bourbon, you'll get a different view: that of a larger-scale operation. As one of the largest sellers of bourbon in the world, their tour seems to reflect that in having one of the more interactive tours. The tour guides are very knowledgable and encourage questions.
Even the most enthusiastic bourbon-lover can't just barrel through and sample bourbon at 9 places all in a rush. You won't be able to fully appreciate every sip if you don't take a break to clear your mind and your palate! Luckily, there's lots to do (and eat) in Kentucky while traveling from distillery to distillery (or rather, from sample of bourbon to sample of bourbon). Eating is important, of course, and luckily, there are tons of local restaurants where you can get a great meal to soak up some of the liquor. Plan to spend at least 2-3 days traveling along the Bourbon Trail, and stop off at some of the many charming Kentucky towns along the route.
The best time of year for a road trip down the Bourbon Trail: Summer is high season along the trail, so you'll have more crowds to contend with, and hotels will be slightly more expensive. A beautiful time of year, however, is mid-September to late-October. You'll avoid most crowds, enjoy off-season hotel prices, and the scenery along Kentucky's rural roads is unsurpassed in autumn. From beautiful fall foliage, to pumpkin patches and farm cider, this is the best time to experience the Bourbon Trail.