Ultimate 5-Day Kentucky Adventure with Cincinnati and Chicago Highlights Itinerary

Start your day with a classic Southern breakfast at MilkWood, offering a fusion of Southern comfort food and Asian flavors. Then, head to the Churchill Downs for an exclusive behind-the-scenes tour of the legendary racetrack and the Kentucky Derby Museum .

Refuel with a lunch at Ramsey's Diner, a local favorite known for its down-home cooking. Afterward, spend the afternoon at Kentucky Kingdom, enjoying the thrilling rides and water park.

Dine at The Village Anchor Pub & Roost, a charming eatery with a relaxed atmosphere and a menu featuring local ingredients. Conclude the day with a visit to the vibrant Bardstown Road area, known for its eclectic mix of shops, bars, and live music venues.

Cross over to Cincinnati and kick off your day with breakfast at Biscuit Belly, where you can enjoy a variety of creative biscuit sandwiches. Then, spend the morning at the world-renowned Cincinnati Zoo and Botanical Garden, home to over 500 animal species and beautiful gardens.

Have a delightful lunch at The Silver Dollar, known for its Southern-inspired cuisine and extensive whiskey selection. Afterward, take a leisurely walk along the Cincinnati Riverwalk and enjoy the scenic views of the Ohio River and the city skyline.

For dinner, experience the farm-to-table concept at Ward426, located in the historic heart of Covington. Afterward, if time allows, catch a performance at the iconic Cincinnati Music Hall or explore the lively nightlife of the Over-the-Rhine district.

Start your day with a breakfast at Bluegrass Burgers, where you can enjoy a variety of locally-inspired dishes. Then, visit the Kentucky Horse Park to learn about the history and heritage of the Bluegrass State and its most famous residents, the thoroughbred horses.

Enjoy a leisurely lunch at The Mayan Cafe, which offers a modern take on traditional Mayan cuisine using locally-sourced ingredients. Afterward, take a guided tour of the Woodford Reserve Distillery, where you can learn about the bourbon-making process and sample some of Kentucky's finest spirits.

Dine at Jack Fry's, a Louisville institution known for its upscale Southern cuisine and live jazz music. After dinner, take a stroll through the historic Old Louisville neighborhood, known for its beautiful Victorian architecture and charming atmosphere.

Begin your day with a delightful breakfast at Butchertown Grocery, known for its artisanal dishes and welcoming ambiance. Afterward, take a morning walk along the Chicago Riverwalk, enjoying the architecture and the serene waters of the river.

For lunch, indulge in the flavors of the South at Holy Grale, a gastropub offering a wide selection of craft beers and a menu inspired by European beer-hall cuisine. Post-lunch, explore the impressive collections at the Art Institute of Chicago, one of the oldest and largest art museums in the country.

Dine in style at Game - Louisville, a restaurant that celebrates the spirit of competition with a menu featuring exotic meats and unique game dishes. After dinner, if you're up for some entertainment, catch a show at the historic Chicago Theatre or simply take a leisurely evening stroll along the Magnificent Mile, enjoying the upscale shops and the vibrant city lights.