Ultimate 6-Day Louisville, Red River Gorge & Door County Adventure Itinerary

Day 1: Arrival & Explore Louisville

Louisville, USA on June 25, 2025

7:00am

Fly Boston to Louisville

Catch a direct flight from Boston Logan Airport to Louisville Muhammad Ali International Airport; flight time is approximately 2.5 to 3 hours via Southwest, Delta, or American Airlines.
USD200, 3h

12:30pm

Pick up rental car & drive to downtown

After landing at Louisville Airport, pick up your rental car and drive 20 minutes to your downtown hotel for convenient accessibility.
USD50, 30m

1:00pm

Lunch at Doc Crow's

Enjoy classic Southern BBQ and local favorites at Doc Crow's, a highly rated spot open daily from 11am-10pm.
USD25, 1h

2:30pm

Explore Downtown Louisville & Waterfront Park

Walk along Main Street and explore Waterfront Park with scenic views of the Ohio River; perfect timing before evening.
Free, 2h

5:00pm

Evan Williams Bourbon Experience

Visit the Evan Williams Bourbon Experience for an interactive tour and tasting; opens 11am to 6pm, book tickets in advance.
USD20, 1h

7:00pm

Dinner at Proof on Main

Dine at Proof on Main, known for its bourbon-inspired menu and farm-to-table cuisine, open until 10pm.
USD50, 1.5h

8:45pm

Evening stroll along Ohio River waterfront

End your day with a relaxing walk along the riverside enjoying scenic sunset views and vibrant atmosphere.
Free, 45m
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Day 2: Red River Gorge Hiking

Red River Gorge, USA on June 26, 2025

7:00am

Drive to Red River Gorge

Depart Louisville early and drive 1.5 hours east to Red River Gorge to maximize cooler morning hiking hours.
USD10 toll + gas, 1.5h

9:30am

Hiking Natural Bridge Trail

Explore the iconic Natural Bridge trail (0.75 miles, easy) to see the natural sandstone arch formation surrounded by forest.
USD4 parking, 1h

11:00am

Optional Gray's Arch Trail

If feeling adventurous, hike the moderate 1-mile Gray's Arch Trail offering beautiful vistas and unique rock formations.
Free, 1h

12:30pm

Lunch at Miguel's Pizza

Enjoy delicious pizza and cool off at Miguel's Pizza, a local favorite near the Gorge operating 11am-8pm daily.
USD15, 1h

2:00pm

Gorge Underground Kayaking Tour

Take a unique kayaking adventure through a flooded limestone mine for an air-conditioned, refreshing afternoon experience; tours usually require advance booking.
USD60, 2h

4:30pm

Scenic Drive & Rest

Enjoy a relaxing drive through scenic viewpoints around Red River Gorge or return to your accommodation for a rest during peak heat.
Free, 1h

7:00pm

Dinner near Red River Gorge

Dine at the nearby Miguel's Pizza again or try local Kentucky comfort food at a nearby eatery before resting.
USD25, 1.5h
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Day 3: Mammoth Cave & Bourbon Trail

Mammoth Cave & Louisville, USA on June 27, 2025

8:00am

Drive to Mammoth Cave area

Drive approximately 1.5 hours from Red River Gorge to Mammoth Cave National Park for a morning exploration.
USD20 gas, 1.5h

9:30am

Mammoth Cave Historic Tour

Choose from the Historic Tour or Domes & Dripstones Tour (book in advance) to explore stunning cave formations and history; cave temperature 54°F so bring light jacket.
USD15, 2h

12:00pm

Surface activities & lunch

Visit Green River trails or the visitor center exhibits; pack a picnic or try the onsite café for light lunch.
USD10, 1h

1:30pm

Four Roses Distillery Tour

Drive to Four Roses Distillery for a 1.5-hour tour and bourbon tasting in an air-conditioned facility; open 9am-4:30pm, last tour 3:30pm.
USD25, 1.5h

3:30pm

Drive back to Louisville

Return to Louisville (1.5 hours) to rest and freshen up for dinner.
USD20 gas, 1.5h

6:30pm

Bourbon-paired dinner at Proof on Main

Indulge in a celebratory dinner with expertly paired bourbon selections at Proof on Main; reservation recommended.
USD60, 2h
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Day 4: Drive to Indiana Dunes

Indiana Dunes, USA on June 28, 2025

9:00am

Leisurely hotel checkout

Enjoy a relaxed morning and optional final bourbon distillery visit if schedule permits before departure.
Varies, 1h

10:00am

Drive to Indiana Dunes

Embark on the approximately 5-hour scenic drive through Indiana countryside to Michigan City or Chesterton area near Indiana Dunes National Park.
USD40 gas, 5h

3:30pm

Check-in & West Beach visit

Check into your lakefront hotel or vacation rental then visit West Beach and the Indiana Dunes Visitor Center; beach open daylight hours.
USD7 parking, 1.5h

5:30pm

Watch sunset at Indiana Dunes

Experience the stunning first Great Lakes sunset at the dunes, perfect for photos and tranquility.
Free, 1h

7:00pm

Dinner at The Shack in Michigan City

Enjoy casual and fresh lakefront dining featuring seafood and local dishes; open evenings until 9pm.
USD30, 1.5h
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Day 5: Door County Day Trip

Door County, USA on June 29, 2025

7:30am

Drive to Door County area

Travel approximately 4 hours north to Baileys Harbor area in Door County, Wisconsin; leave early for full day.
USD40 gas, 4h

11:30am

Visit The Ridges Sanctuary

Explore The Ridges Sanctuary's unique ridge-swale habitats and boardwalk with an easy 2-3 hour nature walk; open 9am-5pm.
USD7, 2h

1:30pm

Lunch at a local Door County cafe

Experience Door County flavors with fresh farm-to-table options, many with vegan-friendly menus.
USD20, 1h

2:30pm

Option A: Washington Island Ferry Tour

Take a ferry to Washington Island to visit School House Beach and Fragrant Isle Lavender Farm with biking or driving tours; ferry runs 7am-6pm.
USD20 ferry, 4h

2:30pm

Option B: Peninsula State Park & Cave Point

Hike Eagle Trail for bluff views, visit Cave Point Park's limestone cliffs, and kayak on Green Bay if weather permits; park open sunrise to sunset.
USD7 park entry, 3-4h

7:00pm

Explore Fish Creek & Dinner

Relax in Fish Creek's charming town and enjoy a farm-to-table dinner showcasing Door County’s local cuisine.
USD35, 1.5h
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Day 6: Explore & Return Home

Door County to Boston, USA on June 30, 2025

8:00am

Morning activities at Indiana Dunes

If not visited before, stop at Cave Point County Park, or do a scenic drive along Door County Scenic Byway; visit local artisan shops for last-minute gifts.
Free to USD10, 3h

11:30am

Drive to Milwaukee/Green Bay Airport

Return rental car and head to Milwaukee or Green Bay airport, approximately 1.5-2 hours drive from Door County.
USD20 gas, 2h

2:30pm

Flight Milwaukee/Green Bay to Boston

Catch an afternoon flight of 2.5-3 hours back to Boston Logan International Airport, concluding your adventure.
USD250, 3h
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