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Kentucky and Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Culinary Delights in Louisville

Morning

Start your day with a delicious breakfast at Biscuit Belly, known for its mouthwatering biscuit sandwiches. After breakfast, take a leisurely walk around the historic Churchill Downs, home of the Kentucky Derby.

Afternoon

For lunch, savor the local flavors at Hammerheads, a popular spot for smoked and grilled dishes. Afterward, visit the Louisville Mega Cavern for a unique underground adventure.

Evening

Enjoy a fine dining experience at Jack Fry's, a Louisville institution. After dinner, take a stroll along the Waterfront Park and enjoy the views of the Ohio River.

Bedtime

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Horse Country and Distilleries

Morning

Have a hearty breakfast at Wallace Station Deli and Bakery before heading to the Kentucky Horse Park to learn about the equestrian history of the state.

Afternoon

For lunch, enjoy a farm-to-table experience at Windy Corner Market. Afterward, visit the Woodford Reserve Distillery for a bourbon tour and tasting.

Evening

Dine at The Village Anchor Pub & Roost in the charming town of Anchorage. After dinner, take a leisurely walk around the historic district.

Bedtime

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Bourbon Heritage and Culinary Gems

Morning

Start your day with a classic southern breakfast at Mammy's Kitchen & Bar. Then, visit the Oscar Getz Museum of Whiskey History to learn about the art of distilling.

Afternoon

Enjoy a leisurely lunch at The Rickhouse Restaurant & Lounge before exploring the My Old Kentucky Home State Park. In the afternoon, take a scenic drive along the Kentucky Bourbon Trail.

Evening

For dinner, indulge in a fine dining experience at Talbott Tavern, a historic landmark in Bardstown. Afterward, enjoy a ghost tour to learn about the town's haunted history.

Bedtime

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Iconic Sights of Chicago

Morning

Arrive in Chicago and start your day with a delightful breakfast at The Bongo Room. Then, head to the Art Institute of Chicago to admire its world-class art collection.

Afternoon

For lunch, enjoy a deep-dish pizza at Lou Malnati's Pizzeria. Afterward, take a stroll along the Millennium Park and visit the Cloud Gate sculpture.

Evening

Dine at Alinea, a three-Michelin-star restaurant offering a unique dining experience. Conclude your day with a visit to the 360 Chicago Observation Deck for panoramic views of the city.

Bedtime

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