Kentucky makes roughly 95% of the world’s bourbon, and Louisville is its lively front porch—where river-town grit meets polished tasting rooms and storied rickhouses. This 3-day whiskey trail itinerary anchors you in Louisville’s Whiskey Row and NuLu, with a day trip to Bardstown, the “Bourbon Capital of the World,” for classic rackhouse aromas and rolling bluegrass hills.

From the 18th-century pioneers who charred oak barrels to today’s award-winning craft producers, bourbon’s story is written in Louisville’s museums, bars, and distilleries. Expect intimate single-barrel tastings, mash bill lore, and a few “Kentucky hugs” (that pleasant bourbon warmth) along the way. Space is limited on tours—reserve ahead, especially on weekends and Derby season (late April–early May) and fall.

Eat well between sips: try a Hot Brown sandwich, country ham, and bourbon-laced desserts. Pace yourself—two tours a day is ideal—and use rideshares, a designated driver, or guided shuttles for bigger tasting days. Most distillery tours run 60–90 minutes and cost about $20–$35; cocktail bars run ~$12–$18 per drink.

Louisville

Louisville pairs heritage and swagger: turn-of-the-century Whiskey Row facades line Main Street, while glass-and-steel tasting rooms buzz in NuLu and Butchertown. You’ll find heavyweight names—Old Forester, Evan Williams, and Angel’s Envy—plus craft darlings like Rabbit Hole and Kentucky Peerless.

• Don’t-miss distilleries: Old Forester (barrel-raising on-site), Evan Williams Bourbon Experience (the origin story), Angel’s Envy (finished bourbon tastings), Rabbit Hole (design-forward, grain-to-glass), Michter’s Fort Nelson (impeccable pours and a stellar cocktail bar), Kentucky Peerless (sweet mash rye lovers, take note).
• Top sights nearby: Frazier History Museum & Bourbon Trail Welcome Center, Louisville Slugger Museum & Factory, Big Four Bridge, Churchill Downs & Kentucky Derby Museum, Cherokee Park by Olmsted.
• Dine well: Proof on Main (artful Appalachian-leaning plates), Jack Fry’s (Old Louisville classic), Repeal Oak-Fired Steakhouse (steak + whiskey), Mayan Cafe (locally sourced Yucatán flavors), Nami (modern Korean steakhouse), La Bodeguita de Mima (Cuban comfort).
• Fun fact: Louisville’s official cocktail is the Old Fashioned—born in the 1800s and beloved citywide.

Where to stay: Base yourself Downtown/Whiskey Row for walkable tastings and museums, NuLu for hip dining and Rabbit Hole, or the Highlands for leafy streets and classic eateries. Browse stays on VRBO Louisville or compare hotels on Hotels.com Louisville. Notable options: 21c Museum Hotel (on-site art), Omni Louisville (pool scene), Hotel Distil (for bourbon buffs), The Brown Hotel (home of the Hot Brown).

Getting there: Fly into Louisville Muhammad Ali International (SDF). Search fares with Trip.com Flights or Kiwi.com Flights. Driving times: Cincinnati ~1.5 hours, Indianapolis ~2 hours, Nashville ~3 hours, Lexington ~1.25 hours.

Day 1 — Whiskey Row Warm‑Up

Morning: Travel to Louisville. If you arrive early, grab a pour-over and a chocolate chip cookie at Please & Thank You (locals swoon for the cookies) or a cappuccino at Sunergos Coffee (award-winning roasts). Check in and hydrate—you’ll be tasting later.

Afternoon: Start at the Frazier History Museum’s Kentucky Bourbon Trail Welcome Center to get your bearings and pick up a trail passport. Walk to Old Forester for a 75-minute tour where you’ll see live barrel-raising and taste through their lineup (plan ~$32). Stroll historic cast-iron facades to the Evan Williams Bourbon Experience for a theater-meets-tasting intro to Louisville’s bourbon roots (about 1 hour, ~$20–$25).

Evening: Dinner on Whiskey Row: Repeal Oak-Fired Steakhouse (Hotel Distil) for dry-aged ribeye and an encyclopedic whiskey list, or Proof on Main for bison marrow bones, country ham, and contemporary Southern plates amid museum-worthy art. Nightcap at The Bar at Fort Nelson (Michter’s) where classics are perfected, or book a hidden-booth reservation at Hell or High Water for speakeasy vibes. Prefer a neighborhood haunt? Try Neat Bourbon Bar & Bottle Shop on Frankfort Ave for rare pours by the ounce.

Day 2 — Bardstown Day Trip: Rickhouses and Heritage

Morning: Coffee at Quills, then depart ~8:30 a.m. for Bardstown (50–60 minutes). First stop: Maker’s Mark in Loretto (about 1 hr 20 min from Louisville). The campus is postcard-pretty—black rickhouses trimmed in Maker’s red—and Chihuly glass installations glow in the distillery. Take the Distillery Tour & Tasting (75–90 minutes, ~$28–$35) and dip your own red-wax bottle in the gift shop.

Afternoon: Drive ~35 minutes to Bardstown Bourbon Company for lunch at Bottle & Bond Kitchen & Bar—think bourbon-brined fried chicken, pimento cheese, and skillet cornbread. Afterward, tour Willett Distillery (75 minutes, ~$25–$30) and try their Family Estate rye, or head to Heaven Hill for the Rickhouse Tasting Experience and a quick museum browse. Stroll Bardstown’s 18th‑century courthouse square for a sweet tea or browse bottle shops for distillery-only releases.

Evening: Return to Louisville (~50–60 minutes). Dinner in the Highlands at Jack Fry’s—a 1933 institution with jazz, shrimp & grits, and excellent Old Fashioneds—or book Nami for Korean wagyu, kimchi flights, and a refined highball program. Cap the night in bourbon-forward bars: North of Bourbon (New Orleans-inspired fare with a bourbon library) or Trouble Bar (Shelby Park; smart flights and welcoming staff). Tip: If everyone wants to taste, consider guided shuttles (e.g., group bourbon tour operators in Louisville; ~$150–$200 per person) or appoint a designated driver.

Day 3 — NuLu Sips, Souvenirs, and Send‑Off

Morning: Biscuits and gravy or a hot honey chicken biscuit at Biscuit Belly, or swing by Nord’s Bakery for a maple bacon doughnut. Tour Angel’s Envy (60–75 minutes, ~$25–$30) to learn about port-finish barrels and enjoy a guided tasting, then wander to Rabbit Hole (NuLu; ~1 hour, ~$25–$30) for design-forward production and a skyline-view tasting deck. Prefer rye? Swap in Kentucky Peerless downtown for superb sweet‑mash releases.

Afternoon: Quick lunch in NuLu: La Bodeguita de Mima (Cuban—vibrant courtyard and ropa vieja), Lou Lou on Market (Cajun-Mediterranean; solid sandwiches and salads), or The Eagle (fried chicken and comfort sides). If time permits before your flight, drop into the Louisville Slugger Museum & Factory for a bat-making tour or the Kentucky Derby Museum at Churchill Downs for a 30-minute track walk and racing lore. Head to SDF for afternoon departure.

Practical tips: Book distillery tours 1–3 weeks in advance for weekends and peak seasons. Most tastings are 0.5–1.5 oz pours; water between sips is essential. Many spots are closed on Mondays—plan accordingly. Expect most tours to run $20–$35; Bardstown lunches ~$15–$25; Louisville cocktails $12–$18. Rideshare is plentiful; parking downtown is straightforward in garages along Main/Market Streets.

Sample costs and times (estimate):

• Louisville ⇄ Bardstown drive: 50–60 minutes each way; gas ~$10–$15 round trip.
• Maker’s Mark tour: 75–90 minutes; ~$28–$35; bottle dipping extra.
• Willett/Heaven Hill tours: ~60–75 minutes; ~$20–$30.
• Angel’s Envy/Rabbit Hole/Michter’s: ~60–75 minutes; ~$20–$35.

Ready to book? Find stays on VRBO Louisville or Hotels.com Louisville, then browse fares with Trip.com Flights or Kiwi.com Flights.

Trip recap: In three days, you’ll taste Louisville’s modern whiskey edge, breathe in Bardstown’s oak-scented history, and dine across one of the South’s most exciting food scenes. Keep the pace relaxed, leave room for a neat pour you’ve never tried, and you’ll head home with new favorites—and maybe a personalized bottle to remember them by.