Music Cities of Deep South USA: Chicago, Memphis & New Orleans by Rail

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Overview

We’re excited to celebrate our 20th anniversary, marking twenty years of helping our valued customers create unforgettable memories. To honour this milestone, we’ve curated a special selection of unique trips in our 20th Anniversary Holiday Collection.

Explore the music cities of the South on this exclusive 10-night rail holiday, available only to American Sky guests. Journey from the soulful streets of Chicago to the heart of Memphis and the vibrant rhythms of New Orleans. Experience the sounds that shaped a nation – from electric blues and rock ‘n’ roll to soul and jazz. Timed to coincide with International Jazz Day, you’ll experience New Orleans pulsing with live music, parades and the unmistakable rhythm of the city at its finest, and a memorable jazz brunch to soak in the sounds and flavours of the day.

In Chicago, enjoy a private behind-the-scenes tour of the legendary Chess Records studio, where the birthplace of blues and rock ‘n’ roll comes to life with rare insights into iconic recording sessions. In Memphis, experience the King’s world with the exclusive “Presley for a Day” tour at Graceland, featuring after-hours mansion access, private golf cart tours and special photo opportunities – an unforgettable encounter for any music fan.

Enjoy scenic train rides, iconic landmarks and vibrant local culture along the way. With fantastic accommodation, unforgettable music experiences and time to explore, this is a journey that celebrates the rhythm and soul of the American South. (TM)

This fantastic itinerary is based on April 2026 and 2027 departure dates, however if you would like to experience a similar adventure, we can tailor make an itinerary to suit your preferred dates and personal interests.

Highlights:

  • Immerse yourself in an exclusive V.VIP experience "Presley For A Day" at Graceland, home to Elvis Presley
  • Experience an exclusive jazz brunch at the Court of Two Sisters on International Jazz Day in New Orleans
  • Enjoy a cocktail making class at the most celebrated bar in New Orleans - the Carousel Bar at the Hotel Monteleone
  • Private boat tour of the Chicago River and Lake Michigan
  • Exclusive guided tour of Chess Records

Itinerary Overview

10 night tour begins Chicago and ends New Orleans: Fly into Chicago 3 nights – Amtrak Sleeper Train from Chicago to Memphis 1 night – Memphis 3 nights – New Orleans 3 nights - Fly home

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • ATOL protection
  • In resort assistance
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Day 1

Chicago

Arrive in Chicago and transfer to the luxurious 5* The Langham Chicago. Enjoy the rest of the day at leisure to explore the city – perhaps choosing to stroll along the stunning Lake Michigan shoreline, discover vibrant neighbourhoods or immerse yourself in Chicago’s legendary music scene. From the birthplace of electric blues to its influential role in Jazz and house music, Chicago offers a soundtrack like no other.

The Langham Chicago is a luxurious riverside hotel offering elegant accommodation and outstanding service. Its spacious rooms, indulgent spa and central location make it an ideal choice for exploring the city in style.

Overnight: The Langham Chicago or similar

Day 2

Chicago

Start your day with a private boat tour along the Chicago River and Lake Michigan, taking in the city’s architectural marvels from the water while your guide shares stories of Chicago’s rich musical and cultural history.

Later, enjoy some free time to continue exploring the city – perhaps choosing to visit a local jazz club or blues bar to experience firsthand the sounds that helped shape Chicago’s rich musical legacy.

Overnight: The Langham Chicago or similar.

Day 3

Chicago

Step behind the scenes of one of music history’s most iconic recording studios with an exclusive, private guided tour of Chess Records – an experience you won’t find anywhere else. Known as the birthplace of Chicago blues and a launching pad for legendary artists such as Howlin’ Wolf, Etta James and Chuck Berry, Chess Records played a pivotal role in shaping modern music.

On this tour, your guide will take you through the original recording spaces, sharing fascinating stories and rare insights into the studio’s legendary sessions. See where iconic tracks were born, learn about the innovative techniques that defined the Chess sound, and hear firsthand about the lives of the artists who made history here.

Overnight: The Langham Chicago or similar.

Day 4

Chicago to Memphis Sleeper Train

Spend the day making the most of your final hours in Chicago. You may wish to take in one of the city’s world-class museums such as the Art Institute of Chicago, or explore Millennium Park, home to the famous Cloud Gate sculpture.

Later, board your overnight Amtrack sleeper train to Memphis, settling in for a comfortable journey as you travel down through the landscapes of the Midwest and South.

Overnight: Chicago to Memphis Sleeper Train

Day 5

Memphis

Arrive in Memphis and enjoy the ultimate Elvis Presley experience with the exclusive “Presley for a Day” tour at Graceland. Your personal concierge and private guide will ensure a tailored, white-glove experience. Explore Elvis’ entertainment complex, airplanes, and mansion with after-hours access and special photo opportunities, while riding in style on a golf cart tour of the grounds.

Highlights include a Graceland Stable & Horse Experience, access to Moriah’s House for a gourmet Southern meal with stunning mansion views, and a behind-the-scenes Graceland Archives Experience. The day concludes with an after-hours mansion tour – the perfect end to a truly incredible experience.

Overnight: The Peabody Hotel or Guesthouse at Graceland or similar.

Day 6

Memphis

Enjoy a day at leisure to explore Memphis at your own pace. Visit the Sun Studio, where legendary artists recorded hits that changed the face of music, or stroll along the Mississippi Riverfront. Music lovers can explore Stax Museum of American Soul Music, while history enthusiasts may enjoy National Civil Rights Museum.

Overnight: The Peabody Hotel or Guesthouse at Graceland or similar.

Day 7

New Orleans

Today, take a scenic train journey from Memphis to New Orleans. As you travel through the Deep South, relax and enjoy the changing landscapes outside your window.

Arrive in New Orleans, a city bursting with vibrant culture, rich history and soulful music. Let yourself be drawn into its lively streets, where every corner offers a new taste, sound or story waiting to be discovered.

Overnight: Roosevelt New Orleans or Hotel Monteleone or similar.

Day 8

New Orleans

Experience one of New Orleans’ most iconic dining traditions at the Court of Two Sisters with their famous jazz brunch, specially timed to coincide with World Jazz Day. This beloved event combines a buffet of classic Creole and Cajun dishes with live jazz music performed in a beautiful courtyard setting. As talented musicians fill the air with soulful tunes, you’ll enjoy a relaxed and festive atmosphere.

After this fantastic dining experience, enjoy the rest of the day at leisure to explore New Orleans at your own pace – whether wandering historic streets, discovering local music or simply soaking up the city’s unique atmosphere.

Overnight: Roosevelt New Orleans or Hotel Monteleone or similar (brunch included).

Day 9

New Orleans

Today is a full day to discover New Orleans however you please. With no scheduled activities, you have the opportunity to follow your interests. You may choose to take a Steamboat Cruise along the Mississippi River, visit the breath-taking St. Louis Cathedral or admire the historic Miltenberger Houses. Savour the delicious taste of beignets or venture outside the city on a swamp tour. New Orleans truly has something for everyone to enjoy.

Overnight: Roosevelt New Orleans or Hotel Monteleone or similar.

Day 10

New Orleans

Enjoy a final day to explore New Orleans at your own pace. Wander the French Quarter, discover hidden jazz clubs, or revisit your favourite spots from earlier in the trip. Perhaps take a last stroll along the riverfront, enjoy a café au lait with beignets, or shop for local crafts and souvenirs. This is your day to soak in the city’s vibrant culture and rhythm one last time before departure.

Overnight: Roosevelt New Orleans or Hotel Monteleone or similar.

Day 11

Departure

After a fantastic journey through America’s musical soul, from the blues of Chicago to the rock ‘n’ roll roots of Memphis and the vibrant jazz of New Orleans, today marks the end of an unforgettable adventure. Fly home with memories of legendary music, rich culture and delicious food.

  • Return international flights
  • 10 nights accommodation as described or similar
  • Amtrak Sleeper train from Chicago to Memphis
  • Amtrak train Memphis to New Orleans
  • Chicago Architecture Cruise
  • Memphis Graceland Mansion VIP Tour
  • New Orleans Court of Two Sisters jazz brunch

What's not included

  • Airport transfers
  • Meals unless stated
  • Optional excursions

Departing 26 Apr 2026 and 27 Apr 2026.

Itinerary may vary slightly to ensure the Court of Two Sisters jazz brunch falls on International Jazz Day (30 Apr 26).

 

The Langham Chicago

Chicago

This luxurious hotel sits close to the sophisticated centre of Chicago

The Peabody

Memphis

In the heart of “Blues City,” you’ll find The Peabody Memphis, a magnificent historic hotel. Legendary, charming, elegant and grand are adjectives that perfectly describe this luxury Memphis hotel.

The Roosevelt New Orleans, A Waldorf Astoria Hotel

New Orleans

This grand hotel is situated in a prime central location, just a short walk from the well-known French Quarter, and close to attractions such as the New Orleans nightlife and Mardi Gras centre. The upscale sanctuary provides a touch of elegance and sophistication amongst the vibrant culture of the city.

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