Jackson Square in New Orleans
Jackson Square in New Orleans - where jazz, art and history meet
Chicago
The glowing Chicago skyline
Graceland and Memphis
From the King’s home to the city’s heart - Graceland and Memphis
New Orleans and jazz band
Iconic New Orleans & the sound of jazz.

VIP Sounds of the South by Rail

10 nights from €9,150 per person Including Flights

Overview

To book your consultation to discuss this incredible holiday from our 20th Anniversary Collection, please call 01 5781640 9am to 5pm Monday to Saturday.

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 when booking with American Sky. Specially designed around International Jazz Day (30 April 2026), this itinerary ensures you’ll be in New Orleans when the city is at its most alive – filled with parades, performances and an unforgettable jazz brunch in one of its most iconic courtyards. From Chicago’s blues roots to Memphis’ rock ’n’ roll legacy and the soulful rhythms of New Orleans, this is a journey through the music that shaped America – with insider access and exclusive experiences you won’t find elsewhere.

Itinerary may vary slightly to ensure departures include International Jazz Day (30 Apr 26).

What makes this tour unique:

  • Private behind-the-scenes tour of Chess Records – usually difficult to arrange, but secured for you with American Sky.
  • Be “Presley for a Day” at Graceland, with a private guide and golf cart throughout the day giving you behind-the-scenes access to Elvis' airplanes and archives, a unique southern gourmet dinner followed by an after-hours tour with exclusive photo ops and white glove experiences.
  • Celebrate International Jazz Day in New Orleans with a jazz brunch at the Court of Two Sisters, timed so you experience the city’s vibrant celebrations at their peak.
  • Enjoy a private cocktail class at the Carousel Bar in the Hotel Monteleone – an exclusive American Sky touch – before a night of live music at Preservation Hall.

Plus…

Alongside these exclusive moments, your journey includes scenic rail rides linking three of America’s most iconic cities, stays in carefully chosen hotels, and time to explore at your own pace. This is not a tour you could easily piece together yourself – American Sky has done the work for you, curating a seamless itinerary that combines rare access, iconic venues, and the unforgettable atmosphere of International Jazz Day in the very place where jazz was born.

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)

Departure Dates

This fantastic itinerary is based on 26 - 29 April 2026 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. 

To book your consultation to discuss this incredible holiday from our 20th Anniversary Collection, please call 01 5781640 9am to 5pm Monday to Saturday.

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance
Why Book with American Sky?
  • Hassle-free - book direct quickly and easily
  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • Low deposits
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We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

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. From the birthplace of electric blues to its influential role in Jazz and house music, Chicago offers a soundtrack like no other. Explore the city with your Chicago CityPass which includes admission to the Skydeck Chicago, 360 CHICAGO Observation Deck, Field Museum and Art Institute of Chicago.

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.

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 a prestigious afternoon tea at The Langham Chicago hotel.

Overnight: The Langham Chicago.

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.

Day 4

Chicago to Memphis Sleeper Train

Spend the day making the most of your final hours in Chicago. 

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. Travel in the luxurious Sleeper Premium class, offering a bed in a private area, cafe service and flexible dining.

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.

Day 6

Memphis

Enjoy a day at leisure to explore Memphis at your own pace, a city alive with music, history and southern charm. The rhythm of blues and echoes of the city's storied past can be felt on every street here.

Overnight: The Peabody Hotel or Guesthouse at Graceland.

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.

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 front row tickets for the legendary Preservation Hall, is a historic venue dedicated to preserving, promoting, and performing traditional New Orleans jazz through intimate, nightly live performances since 1961.

Overnight: Roosevelt New Orleans or Hotel Monteleone (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. New Orleans truly has something for everyone to enjoy.

Overnight: Roosevelt New Orleans or Hotel Monteleone.

Day 10

New Orleans

Enjoy a final day to explore New Orleans at your own pace. Soak in the city’s vibrant culture and rhythms one last time before departure.

Overnight: Roosevelt New Orleans or Hotel Monteleone.

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.

  • International Flights in Business Class. Flights are also available in First Class or Premium Economy to suit your preferences.
  • 10 nights accommodation as described or similar
  • Amtrak Sleeper train from Chicago to Memphis in Sleeper Premium
  • Amtrak train Memphis to New Orleans
  • Chicago CityPass
  • Chicago Private Architecture Cruise
  • Afternoon Tea at The Langham Chicago
  • Memphis Graceland Mansion VIP Tour: Presley for a Day tour
  • 1 Speciality Cocktail at Hotel Monteleone and cocktail making class
  • Front Row Tickets for Preservation Hall
  • New Orleans Court of Two Sisters jazz brunch
  • New Orleans cocktail walking tour
  • Mississippi River Steamboat Jazz Cruise Lunch

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