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2025

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2026

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2027

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From
NZ $9,098 per person

Music City to Windy City

15 days
From Chicago to Nashville
4.7
58 traveler reviews
From
NZ $9,098 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

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2025

Jan
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Mar
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2026

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Feb
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May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

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ChildrenUnder 18

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Plan your adventure:
In-depth Cultural
Immerse yourself in rich history and local traditions
Fully Guided
An experienced guide will be with you for the entire tour
Low Intensity
Travelers can expect some light physical activities
Guided in English
Group Size 12 - 40
Ages 21+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Chicago

    You'll arrive at your Chicago hotel and get settled in. Later there's a welcome meeting where you'll meet your guide, driver, and the rest of the group traveling with you on this music tour.

  2. Day 2

    Chicago

    Your guide takes you through Chicago starting at Navy Pier, where you can get on and off to check out different spots. After that, you'll head to the historic Chess Records location. In the evening, head out for dinner and catch some live blues music at one of the city's well-known clubs.

    Meals
    Dinner (Dinner at blues clubs)

    Included Activities

    • Guided Chicago city tour with hop-on/hop-off stops
    • Visit Chess Records
    • Dinner and entertainment at blues clubs
    Landmarks
    Navy Pier
    Chess Records
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 3

    Chicago to Ann Arbor

    You'll leave Chicago and drive around Lake Michigan. First stop is Gary, Indiana to see the Jackson 5's childhood home. Then it's on to Kalamazoo for food and a brewery. Later you'll head to Ann Arbor for the evening where there's Main Street to walk around with plenty of dining and entertainment choices.

    Included Activities

    • Stop at Jackson 5 childhood home in Gary, Indiana
    • Brewery visit in Kalamazoo

    Optional Activities

    • Food and dining in Kalamazoo
    • Food and entertainment on Ann Arbor Main Street
    Landmarks
    Jackson 5 childhood home
  4. Day 4

    Detroit to Cleveland

    Check out Hitsville U.S.A., the famous home of Motown Records with its museum. There's a quick stop at Woodlawn Cemetery to pay respects to Aretha Franklin, Rosa Parks, and other Motown musicians. From there, head to Cleveland where you'll have free time to walk around downtown on your own.

    Included Activities

    • Visit Hitsville U.S.A. - Motown Records museum
    • Stop at Woodlawn Cemetery

    Optional Activities

    • Downtown Cleveland exploration
    Landmarks
    Hitsville U.S.A.
    Woodlawn Cemetery
    Itinerary Image 1Itinerary Image 2Itinerary Image 3Itinerary Image 4
  5. Day 5

    Cleveland

    After breakfast, you'll visit the Rock and Roll Hall of Fame and Museum, one of Cleveland's main attractions. There's a short driving tour through the city's lakeside areas. Then you'll have the rest of the day free to explore at your own pace, checking out arts, culture, theater, live music, and nightlife options.

    Meals
    Breakfast (Leisurely breakfast)

    Included Activities

    • Visit Rock & Roll Hall of Fame and Museum
    • Short driving tour of lakeside districts

    Optional Activities

    • Explore Cleveland Heights
    • Visit Little Italy
    • Explore Shaker Square
    • Explore Downtown Cleveland
    • Attend theatre and live music performances
    Landmarks
    Rock & Roll Hall of Fame and Museum
  6. Day 6

    Cleveland to Louisville

    Travel south into Kentucky and arrive in Louisville, the state's largest city on the Ohio River. This evening spend time downtown having dinner and catching some local entertainment.

    Meals
    Dinner (Dinner downtown)

    Included Activities

    • Dinner and local entertainment downtown
    Itinerary Image 1Itinerary Image 2
  7. Day 7

    Louisville

    Start with the Muhammad Ali Center dedicated to the legendary boxer from Louisville. You'll have free time to check out museums and landmarks including the Louisville Slugger Museum and Factory where Major League bats get made. There's also a short trip to Owensboro to see the Bluegrass museum.

    Included Activities

    • Visit Muhammad Ali Center

    Optional Activities

    • Louisville Slugger Museum and Factory
    • Museums and landmarks in Louisville
    • Visit Bluegrass museum in Owensboro
    Landmarks
    Muhammad Ali Center
    Louisville Slugger Museum and Factory
  8. Day 8

    Owensboro to Memphis

    Begin with the Bluegrass museum, then head to Central City for the Everly Brothers Museum. After that, you'll travel to Memphis and check into your hotel. Later there's free time to explore Beale Street and see what it has to offer.

    Included Activities

    • Visit Bluegrass museum
    • Visit Everly Brothers Museum in Central City

    Optional Activities

    • Explore Beale Street
    Landmarks
    Everly Brothers Museum
    Beale Street
  9. Day 9

    Memphis

    After breakfast, spend time at Sun Studio exploring the Million Dollar Quartet exhibit, then visit Graceland Mansion to honor Elvis Presley. There's a brief driving tour of the city with a photo stop at the historic Lorraine Motel. Later you'll have free time to try Memphis BBQ and experience the blues on Beale Street.

    Meals
    Breakfast

    Included Activities

    • Breakfast
    • Visit Sun Studio
    • Visit Graceland Mansion
    • Driving tour including photo stop at Lorraine Motel

    Optional Activities

    • Memphis BBQ dining
    • Beale Street blues clubs
    Landmarks
    Sun Studio
    Graceland Mansion
    Lorraine Motel
  10. Day 10

    Memphis to Muscle Shoals

    A two-hour drive takes you to Muscle Shoals, Alabama, known as the Hit Recording Capital of the World. You'll tour recording studios, listen to live music, and learn about the famous musicians who got their start in this area.

    Included Activities

    • Tour recording studios in Muscle Shoals
    • Live music experience

    Optional Activities

    • Learn about Alabama's famous musicians
  11. Day 11

    Tupelo - Red Bay

    This is a round-trip day from Muscle Shoals into Mississippi to visit Tupelo, Elvis Presley's birthplace, and Red Bay, Alabama where country music star Tammy Wynette was from. You'll head back to the Shoals for live music at the Rattlesnake Saloon, a unique kind of venue.

    Included Activities

    • Visit Tupelo, birthplace of Elvis Presley
    • Stop in Red Bay, Alabama
    • Live music at Rattlesnake Saloon
    Landmarks
    Elvis Birthplace
    Rattlesnake Saloon
  12. Day 12

    Muscle Shoals

    Continue exploring the Muscle Shoals area with more music and attractions. You'll see Ivy Green, Helen Keller's childhood home, and the W.C. Handy Home where the Father of the Blues started out. Another night of live local music rounds out the evening.

    Included Activities

    • Visit Ivy Green (Helen Keller childhood home)
    • Visit The W.C. Handy Home
    • Live local music performance
    Landmarks
    Ivy Green
    W.C. Handy Home
  13. Day 13

    Muscle Shoals to Nashville

    Spend a couple of hours at the Alabama Music Hall of Fame learning about the many famous musicians from the state. After that, head back to Nashville, Tennessee, where you'll have plenty of free time to walk around and explore the city.

    Included Activities

    • Visit Alabama Music Hall of Fame

    Optional Activities

    • Explore Nashville
    Landmarks
    Alabama Music Hall of Fame
    Itinerary Image 1
  14. Day 14

    Optional Franklin and Hendersonville

    You have the option to take a trip to Franklin in southern Kentucky, a charming town with a beautiful courtyard square where Johnny Cash and June Carter got married. See the Lake House in Hendersonville where they lived and their final resting place. Back in Nashville, there's time to explore the Opryland area with shopping, restaurants, live music venues, and various attractions.

    Meals
    Lunch (Lunch at Mennonite Community in Franklin)

    Optional Activities

    • Trip to Franklin, Kentucky
    • Lunch at Mennonite Community in Franklin
    • Visit Johnny Cash and June Carter Lake House in Hendersonville
    • Visit their final resting place in Hendersonville
    • General Jackson Showboat cruise
    • Explore Opryland Hotel
    • Visit Nashville honkytonks
    • Nashville Palace for food and live music
    • Shopping and dining at Opry Mills
    • Madame Tussauds at Opry Mills
    Landmarks
    Franklin Town Square
    General Jackson Showboat
    Opryland Hotel
    Nashville Palace
    Opry Mills
    Madame Tussauds
  15. Day 15

    Nashville

    On your final day in Nashville, visit the Centennial and Bi-Centennial Parks and make sure to see the Parthenon. Stop by Lower Broadway to shop for cowboy boots and hit up Printers Alley in the evening for nightlife before you head out on your next journey.

    Included Activities

    • Visit Centennial Park
    • Visit Bi-Centennial Park
    • Visit The Parthenon

    Optional Activities

    • Shop for cowboy boots on Lower Broadway
    • Nightlife on Printers Alley
    Landmarks
    Centennial Park
    Parthenon
    Lower Broadway
    Printers Alley
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Travelling Time

4.7
(58 reviews)

Number of tours

13

Age Range

21 to 80 years old

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within 3 days

Response rate

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Travelling Time are providers of music themed holidays and tours to the USA...

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Customer Reviews

  • Lorna
    · May 12th, 2025
    "Soundtrack of the South" Well, what can I say? We had a fantastic time in the USA on our tour. I spoke to Lynda on the phone, and I knew straight away this was the company to book our tour with, and I am so glad we did. Lynda was brilliant; the itinerary was well-planned, and the accommodation and restaurants that had been booked were all very nice. I highly recommend Time Travel Holidays, and we will be booking another tour in the future. Thanks again, Lynda, Donna, Richard & Suzanne. We had the best time! xx
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Jan
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Sep
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2026

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Jul
Aug
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2027

Jan
Feb
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Apr
May
Jun
Jul
Aug
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
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Sep
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Dec

2027

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Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

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ChildrenUnder 18

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Good to Know

Tour ID: 220432

  • Currency
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  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before February 13th, 2026 a full payment is necessary. For tours departing after February 13th, 2026, a minimum payment of 30% is required to confirm your booking with Travelling Time. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 70 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Travelling Time will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Travelling Time" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2025

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec