Back to The Deep South Tours

Why We Love It

Historic Kentucky Bourbon Trail

Culture & history of the Deep South

Experience the Country Music Capital

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Day by day Itinerary

Blues & Booze

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Day 1


Arrive into Chicago to begin your trip.

Day 2


Enjoy an architectural river cruise and later, tour Oak Park for Ernest Hemingway and Frank Lloyd Wright historic sites.

Day 3

Chicago - Indianapolis

Travel south for Indianapolis and explore the historic Fountain Square. Enjoy dinner in the trendy Wholesale District.

Day 4

Indianapolis - Louisville

Visit the famed Indianapolis Motor Speedway, before continuing on to Louisville. Here, stroll downtown’s Whiskey Row, where you may enjoy distillery tastings.

Day 5


Today make a visit to Churchill Downs, site of the renowned Kentucky Derby.

Day 6

Louisville - Nashville

In Nashville visit the Country Music Hall of Fame, and dance your night away in the Honky Tonks along Broadway.

Day 7


Visit Ryman Auditorium home of the Grand Ole Opry, and perhaps take in a show.

Day 8

Nashville - Memphis

Continue onto Memphis, making a stop en route at Belle Meade Plantation. Spend the evening under the lights of Beale Street.

Day 9


Visit the Rock ‘n’ Soul Museum and Elvis’ Graceland.

Day 10

Memphis - Vicksburg

In Vicksburg visit the Civil War battlefield.

Day 11

Vicksburg - New Orleans

Visit old plantations along the Mississippi River.

Day 12

New Orleans

Visit the Garden District, Arts District and French Quarter. Take a paddlewheeler dinner cruise on the Mississippi River to complete your adventure.

Day 13

New Orleans

Finish your trip in New Orleans.

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