First off, pronounce it as the natives do: Loo-vul. Or Luh-vul. Or be Mexican and pronouce it Lu-bo. But make sure to say “Louisville” in two syllables. And whatever you do, don’t pronounce it Lou-ee-ville—that’ll mark ya as a tourist, and while no one will throw shade at you, it’s better to get one of those sunny Kentucky smiles when you say the city’s name right.
I’ve spent a good week each summer for the past decade in the Derby City as a base for my Kentucky adventures. And I have seen it explode. This most northern of southern cities (or most southern of northern cities, depending on which side of the Mason-Dixon line you stand) has new developments, new restaurants and new residents who appreciate the charm of the old city but are ready to push the town onto its proper national stage. Screw Nashville, fuck Charleston, and a big meh to Savannah: Get thee to Louisville, and make sure to buy a T-shirt at the Louisville Visitor Center (301 S. Fourth St., 502-379-6109; www.gotolouisville.com/visitor-center) that states the five acceptable ways to pronounce it. Not only that, but those five correct answers are on ads outside offices for the public to see—Louisville takes its grammar seriously.
The one thing this guide won’t have is distillery tours because that’s a whole day unto itself. Besides, you should enjoy the city before you get blotto on bourbon, son!
6:30 p.m.: Arrive at your hotel, tired and hungry. There are no direct flights from Southern California to Louisville just yet, and the city is on Eastern Standard Time, so take the first flight out of LAX or John Wayne Airport so you can get to Louisville International Airport in the late afternoon. Pick up a rental car, then figure out which of the city’s iconic hotels you want to stay at. The horsey set likes to stay at the Brown Hotel (335 W. Broadway, 502-583-1234; www.brownhotel.com), a comfortable, if dowdy inn with a fabulous bar and the home to the legendary Hot Brown, an open-faced turkey sandwich baked in Mornay sauce that makes a Monte Cristo seem as austere as kale chips. Want more glamour? Walk two blocks to the Art Deco-era Seelbach Hilton (500 S. Fourth St., 502-585-3200; www.seelbachhilton.com), where Leonardo DiCaprio’s The Great Gatsby was partially filmed because this is where F. Scott Fitzgerald holed up to write his Great American Novel. Even better is its bar, which invented the hotel’s namesake cocktail: champagne and bourbon, a combo even more potent than it sounds. Count yourself blessed, by the way, if you can manage a drink in its Rathskeller, a former speakeasy done Bavarian-style that’s generally not open to the public.
But the hip hotel in Louisville is the 21c Museum Hotel (700 W. Main St., 502-217-6300; www.21cmuseumhotels.com/louisville), part of a chain across the Midwest and South that combines art, drinks, food and comfort for a hell of an experience. I’ve never stayed at the 21c, but I constantly visit its gallery because it consistently features great exhibits. More important, the hotel also houses Proof On Main (702 W. Main St., 502-217-6360; www.proofonmain.com), a New Southern restaurant with a killer cocktail program. Dine here and drink, go to the Seelbach and drink, then end at the Brown and drink—or shuffle at will.
8 a.m.: Eat a Mexican breakfast at Con Huevos (2339 Frankfort Ave., 502-384-3027 www.conhuevos.com). Don’t snicker: Husband-and-wife owners/chefs Jesús Martínez and Izmene Peredo are natives of Mexico City and Guadalajara, respectively, and know their way around chilaquiles, breakfast tortas and fabulous chicken tinga tacos. Con Huevos would kill it in SanTana; in Louisville, it’s rightfully a city obsession.
9 a.m.- 2 p.m.: Distillery tour time! Don’t sign up with one of the official tours—follow our own handy-dandy guide. Today, focus on the Louisville distilleries because Loovul.
2:30 p.m.: The up-and-coming part of Louisville is called NuLu, so start at one of the pioneers, Muth’s Candies (630 E. Market St., 502-585-2952; www.muthscandy.com). Run by the same family for 96 years, it makes all sorts of candies but is most famous for two sweets: bourbon balls and Modjeskas, a chewy caramel-mushroom confection named after our own Madame Helena Modjeska after she wowed them back in 1883 by staging the first American production of A Doll’s House. After you load up, walk down Market toward Revelry Gallery (742 E. Market St., 502-414-1278; revelrygallery.com), a charming boutique that stocks posters, craftwork and other handmade doodads from local artists. Then go thrifting at Joe Ley Antiques (615 E. Market St., 502-583-4014; www.joeley.com), located in a humongous Victorian home crammed from massive basement to dining room to stairs with every primitive (what Southerners also call antiques) imaginable. Don’t be bewildered by the pricing system consisting of letters—it’ll make sense. And score your humble Mexican a bourbon decanter, por favor.
While you won’t have time to eat or drink at the excellent Garage Bar (700 E. Market St., 502-749-7100), take a picture with the smashed-up cars in front of it. Good times!
5 p.m.: Let’s leave NuLu for a bit and head west toward Louisiville’s downtown. The best bourbon bar in the city is Down One (321 W. Main St., 502-566-3259; www.downonebourbonbar.com), with its incredible 170 bourbons available. Try a flight or five, then cross the street to Milkwood (316 W. Main St., 502-584-6455; milkwoodrestaurant.com), the casual eatery of acclaimed chef Edward Lee (don’t bother with his James Beard-nominated 610 Magnolia, which has a months-long reservation list). Just get a couple of his awesome Asian-Southern snacks because you’re saving your gut for . . .
7 p.m.: Harvest (624 E. Market St,. 502-384-9090; www.harvestlouisville.com) is farm-to-table dining at its finest—and not just because there’s a map on the wall with pins signifying the location of each farm from which Harvest buys its products or because the restaurant has large black-and-white photos of said farmers adorning its wall. The food is delicious and seasonal, and they’re not above doing a vegetarian take on burgoo, a Kentucky stew that has historically included everything from turtle to squirrel.
8:30 p.m.: Cross the street and get a salbute at Mayan Café (813 E. Market St., 502-566-0651; themayancafe.com). It’s hard enough to sell Yucateco cuisine in Southern California, but in Kentucky?! It takes a madman like Bruce Ucan, who has been doing it since the late 1990s(!). His salbutes, fried perfectly, are delicious, but his most famous dish is, of all things, lima beans—the best you’ll ever have, spicy and toasted and perfect.
8 a.m.: There used to be an amazing breakfast spot called Hillbilly Tea, which served Appalachian cuisine infused with tea flavors. But the restaurant had a mysterious provenance—super-popular, then closed, then opened bigger and better, and now done. More straightforward is Toast On Market (620 E. Market St., 502-569-4099; www.toastonmarket.com)—good, traditional brekkie. Eat as much bread as possible because you need to line your stomach for . . .
9 a.m.- 3 p.m.: Distillery tour time again! Today, go on the Bourbon Trail—take your pick.
3 p.m.: Sad that you couldn’t get to that one distillery? Load up at Old Town Wine (1529 Bardstown Rd., 502-451-8591; www.oldtownwine.com), the Hi-Time Wine Cellars of Louisville. Pro-tip: Skip the Evan Williams and Very Old Barton tours because those brands are mucho barato.
It’s not all boozing and eating in Lubo, so get nerdy at Carmichael’s (1295 Bardstown Rd., 502-456-6950; also at 2720 Frankfort Ave., 502-896-6950; www.carmichaelsbookstore.com), the city’s oldest independent bookstore. Since you’ll probably want to catch some live music or at least weirdos afterward, go to the Bardstown location, as that’s the city’s hipster corridor.
5:50 p.m. This is the latest flight I can find out of Louisville—damn, you barely did anything! Really, you need three nights to experience this fabulous city. I didn’t even tell you about the barbecue spot; the place where you can load up on American caviar; or Lilly’s Bistro (1147 Bardstown Rd., 502-451-0447; lillysbistro.com), a female-run restaurant that’s one of the most criminally underrated spots in the South. And I didn’t give big plugs to the Louisville Slugger Museum (800 W. Main St., 877-775-8443; www.sluggermuseum.com), the Muhammad Ali Center (144 N. Sixth St., 502-584-9254; alicenter.org), or anything related to the Kentucky Derby or the University of Louisville, the city’s two true religions. So many things to do, so little time. . . . Y’all come back now, ya hear?