Explore Americas Deep South on this Jazz, Blues & Rock n Roll Rail Vacation, which runs from Chicago to New Orleans. On this Rail tour you will travel through the home of Blues & Elvis Presleys stomping ground Memphis, Tennessee!
If your previously read our post on Blues Highway 61 – Nashville to New Orleans Road Trip:you will known this is definitely a rail journey not to be missed! Filled with traditional Southern hospitality, foods & Musical wonders!
8 Day Itinerary: Jazz, Blues & Rock n Roll Rail Vacation
Day 1 & 2: Chicago
We start our Rock n Roll Rail Vacation in Chicago, the “Windy City”. Chicago is a vast metropolis on the Scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the Willis Tower (Former Sears Tower) and the Legendary John Hancock Center which stands over 1,451ft high.
Chicago is also known for Chicago style pizza (Deep dish) , and Chicago hot dogs in addition to Jazz and of course the Notorious 1920s gangster Al Capone.
How many days should I spend in Chicago?
We recommend spending at least 2 days in Chicago to really experience what it has to offer!
6 Unique Things to do in Chicago:
1. Millennium Park – FREE!
Millennium Park is not just a public park, its a true expression of the Chicago experience! It is the largest public space inside the 319 acres of Chicagos Grant Park, located downtown. This area includes, gardens, sculptures and attractions.
Crown Fountain was designed by Spanish artist Jaume Plensa the fountain is made up of two 50 foot glass block towers which of display rotating images of over 1000 Chicago residents.
The fountain fires water out of the giant mouth and is really popular with kids during the summer months.
Other highlights at Millennium Park include, Lure Garden and Maggie Daley Park. A large 20 acre adventure park which includes rock climbing, slides and mirror walks
Cloud Gate (The “Bean”)
A Large public sculpture weighing in at over 110tones and is over 66 feet long and 33 feet high. This is an astonishing sculpture to see and was designed by British Artist Anish Kapoor.
Where is it?
201 E Randolph St, Chicago, IL 60602, United States
2. Navy Pier
Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan. Here you will find many fairground rides & attractions including a 360 Chicago, (A Premiere observation deck), Centennial Wheel (Observation Wheel) Museum of Contemporary Art, the Childrens Museum, River Cruises and many more!
3. Willis Tower (“Sears Tower”)
The Willis Tower is a 110-story, 1,450-foot skyscraper in Chicago. When it was completed in 1973, it surpassed the World Trade Center in New York to become the tallest building in the world!
Skydeck Chicago offer views from 103rd floor of the former Sears Tower with clear observation boxes & views extending to four states!
4. Green Mill Lounge – Can you spot Al Capone??
Head back to the 1940s at Chicagos Green Mill Lounge. Here you can find local Jazz Musicians, poets and was once a hangout for the Notorious Gangster Al Capone.
5. Shedd Aquarium
Shedd Aquarium is one of the largest indoor Aquariums in the world! It was opened back in the 1930s and houses over 32,000 animals!
6. Take a river cruise!
Taking a River Cruise through Chicago is one of the most unique ways of seeing the city! It’s a great way to learn about the downtown area and get your bearing if you’ve never been here before. To book a recommend tour follow this link HERE
Where to Eat?
Best Drive in – Superdawg – Is a throwback Chicago dining experience, which serves an immersive variation of a Chicago style hotdog. Expect thick all-beef sausage. mustard, pickled green tomato, and chopped Spanish onions.
Address: 6363 N Milwaukee Ave, Chicago, IL 60646
Best for Lunch: Smoque BBQ is probably the best in town! Here you will experience mouth watering, St. Louis-style ribs, tender brisket, apple-and-oak-smoked pulled pork and more.
Address: 3800 N Pulaski Rd, Chicago, IL 60641
Best for Dinner – Passerotto is an Asia Italian fusion restaurant which delivers modern Korean food with Italian touches.
Where to Stay?
For a recommended list of my favourite places to stay in Chicago follow the link HERE.
Day 3: Amtrak Sleeper Train
Head to the Railway Station and hop on the Board Amtraks City of New Orleans for an overnight trip to Memphis, Tennessee.
Day 4 & 5: Memphis
Welcome to Memphis, Tennessee! This is the ultimate place to learn about the history of Blues, Soul and Rock ‘n’ Roll, its one of the major highlights of our Rock n Roll Rail Vacation. Check out the famous Sun Studio, where Elvis Presley, B.B King and Johnny Cash all recorded albums. Other popular attractions include Graceland Mansion, Elvis Home and final resting place.
Where to Eat in Memphis?
Paulette’s Restaurant is an iconic and charming eatery which offers an inventive menu of French & Hungarian dishes along with regional eats.
Address: 50 Harbor Town Square, Memphis, TN 38103, United States
Cozy Corner Restaurant
This place offers one of the best Barbecues in town, take a seat in one of the torn vinyl booths and enjoy some of the mouth watering ribs & wings. The Cornish game hen ($11.75) is unreal aswell!
Address: 735 North Pkwy, Memphis, TN 38105, United States
Where to Stay in Memphis?
If you plan on staying in downtown Memphis I recommended:
La Quinta Inn & Suites – A superb hotel in Downtown Memphis. There is an indoor swimming pool, free parking on site and free WiFi throughout the hotel.
SpringHill Suites – SpringHill Suites is another favourite with an outdoor swimming pool and a sun terrace. The rooms are studio style with a refrigerator and a microwave for preparing basic meals.
There are tea and coffee-making facilities in every room. They also allow guests to use their gym and business center.
If you are a Elvis Fan, then you should definitely stay at: The Guest House at Graceland – A fantastic hotel which is just a five-minute walk from the gates of the Iconic Graceland Mansion, home of Elvis Presley. There are two restaurants in-house and an outdoor swimming pool.
Each evening be sure to tuck into the complimentary peanut butter & jelly bar!
For more on Memphis, Mississippi and Nashville, Check out: Nashville to New Orleans Road Trip: Blues Highway 61
Day 6: Memphis to New Orleans Amtrak
Head to Memphis railway station and board the Amtrak train to New Orleans! The distance is approximately 359.39 miles, or 578.23 kilometers. The average travel time for a train between these two cities is around 9 hours and 7 minutes. So you will be likely want to head to your hotel straight after arriving.
Day 7: New Orleans
New Orleans is a city with soul, history and great locals who really go out of there way to make sure your have a fantastic time. Expect that famous “Southern Hospitality” to not disappoint! I recommend staying here for at least 3 nights!
With “Let the Good times Roll” as New Orleans unofficial motto this is a true symbol of the vibes expected. From the Garden District and Jazz clubs to the bustling Bourbon Street.
After the rebuild from Hurricane Katrina the city has been injected with a new lease of life with the people more optimistic and welcoming than ever.
Madi Gras Festival:
If You a traveling here in late February (25th) you may get to experience the world renowned Mardi Gras Festival and Parade!
For more info see: 12 Epic Parades in the U.S.A
Evening Jazz Cruise & Recommend Tours:
One of my wives favourite things to do here was the Evening Jazz boat cruise with dinner. This was a perfect excuse to freshen up after that long rail Journey.
- Evening Jazz Cruise
- Bayous 2 Hour Swamp/boat Tour
- High Speed Airboat Ride (This is great for groups of friends!)
- New Orleans Day Cruise – Steamboat Natchez
Be sure to book your tours in advance as the best ones can sell out fast, especially during peak season!
For something a little difference the Hurricane Katrina tour is a real eye opener to what went on in the great city. See: Which are the Best Travel Tours?
Where to Eat in New Orleans?
Top foods you must try in New Orleans include:
- Muffaletta sandwich from Central Grocery Co.
- Jumbalaya from Remoulade in the French Quarter.
- Beignets and a Cafe au Lait at Cafe du Monde.
- Lobster PoBoy from GW Fins
- Turtle Soup from Commander’s Palace.
Other foods to try here include: Deep Fried Soft Shell Crab and Raw Oysters!
Where to Stay in New Orleans?
I suggest staying in Louisiana for a minimum of three nights to really experience what the place has to offer! I recommended:
Hotel Monteleone – French Quarter
Family-owned and operated since 1886, the historic Hotel Monteleone is one of the most famous in New Orleans. Its luxury rooms were favoured by writers like Truman Capote. Tennessee Williams, and William Faulkner. A highlight of the hotel is the Carousel Bar which offers classic cocktails and musical entertainment,
Royal Frenchmen Hotel – Bywater (Trendy Neighbourhood!)
A renovated Creole townhouse which has everything you need, from cozy, well-appointed rooms with a vintage vibe to a great hotel bar serving craft cocktails. There is a tranquil courtyard and opulent lobby lounge for guests. You also located very close to the action on Frenchmen.
When you arrive ask if you can have a room with a balcony overlooking the street, to really take in the New Orleans Atmosphere.
Would you like the best deals when booking a train?
Try out our: Best Public Transport Booking Tools
Do you have a decent Camera??
If not, Check out our Recommended Travel Photography Gear
Want to know the secrets of great Hotel Deals?
See this essential post: How to find the Best Hotel Deals??
Got everything else you need?
Check out our Travel Essentials (Things You can’t travel without!)
If your still not convinced by trains and would still like to rent a car Check out: Ultimate Car Rental Travel Hacks!