We really love unusual itineraries, those that combine the classic with the lesser known, the ones that you could easily lose because on roads less traveled. We love to create customized routes, to study every single stop not only where to sleep but also between points. An travel itinerary in the United States to me is this: discovering mile after mile the usual and especially the unusual, finding “my places” by creating a trip made for ourselves.
Each trip is the result of study and research. Something I am passionate about! So, even on this latest trip, I started from classic itineraries to create one customized to our tastes, discovering new places and rediscovering others already seen, to see things we missed. A circular itinerary that begins and ends in Chicago, passing through Detroit, Indianapolis, Nashville, Memphis, then back up to Springfield in Missouri, Route 66 to St. Louis, and then ends in Chicago, the city we love the most in the United States.
The central themes of this itinerary, which pass through the Midwest and a small part of the Deep South, are different. They range from discovering American cars in Detroit, Auburn and Branson, to music with Nashville, Memphis and St. Louis, via the Midwest’s Route 66-from Springfield, Missouri, to Chicago – and, of course, lots of unusual movie locations, such as Candy Candy’s Lake (but not only that: there’s also a beautiful museum in Branson that combines cars and movies!). An exciting route that also touches many important points in American history and culture.
A little useful tip first: to be connected everywhere without any problem (both for work matters and for family contacts given the time difference), we purchased a prepaid Travel Sim that worked great. I will link it in case it is useful.

Travel itinerary in the United States: Days 1 and 2, Chicago
You arrive at O’Hare International Airport, voted among the best airports in the United States. Alternatively, there is the Midway, but the flights are more expensive and the location less connected.
For sleeping I recommend the Felix Hotel, very close to the Magnificent Mile, very nice, comfortable and cheaper than others in the area (here is a Facebook post in which I show some photos). It also has nearby parking in case you need it for your car, and you can download the SpotHero app to reserve your parking spot (applies to the whole U.S.!) by paying it at a discounted rate.
Or, if you want a special stay, the Drake Hotel is a historic Chicago hotel, rightfully entered in the Historic Hotels of America, with timeless charm. Centrally located and luxurious, it has recently been renovated to offer better services and keep up with the city’s evolution, while keeping its historic identity intact.
On this itinerary, the time we devoted to Chicago was very little (2 days) but we already had visited it before. If this is your first time visiting, I recommend that you dedicate at least three days to the Second City.
This time we focused on Street Art, visiting the neighborhoods of Logan Square – where the murals of Robin William, Quincy Jones and Greetings from Chicago are located – Wicker Park and the Wabash Corridor in the South Loop, where you can see twenty large murals in just seven blocks.

We then visited Oz Park, the park dedicated to the Wizard of Oz – perfect for children! -, to say hello to Dorothy in her red slippers, the Tin Man, the Lion and the Scarecrow. The park was built in 1974 and dedicated to Lyman Frank Baum, the author of the Wonderful Wizard of Oz novels, a work that was immortalized in the 1939 MGM Movie (there were several film adaptations but this one with Judy Garland was the most famous). In 1891 Baum moved to Chicago, a few miles away from the park, where he wrote all his novels, including the 14 novels about the Wizard of Oz.
A tour of Millennium Park is always a must when visiting Chicago, in all seasons. This time we saw it in winter and it is beautiful with the ice skating rink before The Bean and the 16-meter-tall Christmas tree that had lit up the Park every year for 109 years from late November to early January.
We concluded with a visit to 360Chicago, a scenic and adrenaline-pumping attraction not to be missed, from which you can see the most beautiful views of Chicago from above.

Day 3: St. Joseph
Leaving Chicago, we set off eastward, toward Michigan. The first stop in this state was St. Joseph (about a two-hour drive from Chicago), or St. Joe as they call it, a town on Lake Michigan, especially famous in the summer as a seaside resort. We chose it to see the lake – the one Candy Candy grew up on – from a different angle, to see the lighthouse and its beach. A quiet little town, perfect in winter to relax and see one of America’s lighthouses (in winter, when it’s freezing, it’s a lovely sight). A lighthouse that contends the title of first lighthouse built on Lake Michigan.
Also at Silver Beach, a powered glider was brought by Augustus Moore Herring on October 11, 1898, which flew for 7 seconds, and eleven days later for 10 seconds but losing control of it. Its time was beaten five years later by the Wright brothers at Kitty Hawk, taking the place in history that might have belonged to Herring and St. Joseph.

Days 4, 5, 6: Detroit
With a three-hour drive from St. Joseph we reached Detroit.
Famous for cars and known as the “Motor City,” Michigan’s largest city actually offers many unexpected opportunities for travelers, something that – I admit – I would not have imagined before I set out to study the itinerary. Cars, music, art, food-there really is something for everyone and it amazed me. It has also been used as a set for many movies and a tour among its film locations is not to be missed!
For sleeping I recommend the Element Detroit at Metropolitan, downtown, clean, with great rooms and a good breakfast. It also has a valet parking service included (you leave your car at the hotel’s entrance and when you have to leave you send a text message and they bring the car back outside the hotel). You can see a reel we dedicated to it here.
The first day, since we arrived at lunchtime, we stopped at Ford’s Garage Restaurant fully immersing ourselves in the Detroit atmosphere. Afterwards, we dedicated ourselves to Downtown by strolling along Woodward Avenue – one of America’s most iconic streets, which I will tell you more about – to Campus Martius Park and the nearby Monroe Street Midway, which were set up for Christmas, with lots of family activities, the inevitable ice skating rink, a house with Santa Claus, and a market with wooden playhouses.
Afterwards we visited the wonderful Guardian Building, the Fisher Building and made a quick stop at the Grand Trunk, the pub carved out of what used to be the Grand Truck Railway ticket office.
To end our first day in Detroit on a high note, we went to Baker’s, the oldest Jazz Club in the world still in operation, with its distinctive piano keyboard-shaped bar.

We spent the beginning of our second day in Detroit on movie locations, hunting for the sets of Batman and Gran Torino, and then on to Ford, to visit the sites of an ad-hoc itinerary – which I will write about thoroughly- dedicated to the world’s most famous American car brand. We visited the Ford House, the home of Edsel – Henry Ford’s only son – and Eleanor Ford. Upon Eleanor’s death, by her will the house was opened to the public, making it a place for anyone to go, walk around, have a picnic and find out a little more about the Ford family. It is an unusual place, off the beaten track, and well worth a visit. The complex is divided in two parts: the Visitor Center, where a number of cars are on display and various activities are organized (we, for example, made a DIY Christmas card workshop!) and the house, where one arrives accompanied by a bus from the Visitor Center, inspired by the style of the Cotswolds in England. The house is beautiful and cozy, you can visit it freely and it is like feeling in the beautiful home of a friend.
In the afternoon we visited the Henry Ford Museum of American Innovation, a museum dedicated to innovation in all fields: appliances, furniture, technology, automobiles, airplanes, etc…. It also houses the only remaining prototype of the Dymaxion House, the aluminum house designed to be the strongest, lightest and cheapest house ever built by architect R. Buckmister Fuller.
The museum also hosts temporary exhibitions-we were lucky enough to see the one of Disney’s costumes! – the Ford Rouge Factory Tour, a tour of car and truck production between past and present. What absolutely is not to be missed, is Greenfield Village, a complex of historic buildings in which the stories of the American characters who made history (and more) are told, as well as the house where Henry Ford was born, the car in which President Kennedy was killed, and much, much more (I recommend visiting from the morning so you can enjoy everything at your pace and for as long as you like).


Finally, on the third day we continued to look for movie locations and then returned to Downtown to see the Spirit of Detroit Plaza, with its beautiful sculpture of the same name, “The Fist” monument, a sculpture dedicated to boxer Joe Louis, Hart Plaza and the International Memorial to the Underground Railroad, a tribute to Detroit’s role as the “Gateway to Freedom,” the gateway to Canada and freedom for slaves (I will explore this topic further as well). After a brief tour to hunt for Street Art, we headed to the Ford Piquette Avenue Plant, the birthplace of the Model T. Built in 1904 and operational until 1909 it is the oldest Ford plant still in existence, and is listed on the National Register of Historic Places. It is an extremely fascinating place for me, where everything is still as it was in the days when the factory was active, and there are plenty of Model T models on display, a car that I personally still find beautiful today. I would definitely put this one on the must-see list in Detroit!


Days 6 and 7: Indianapolis
After visiting the Ford Piquette Plant, we left Detroit to drive down to Indianapolis (about a 4 and a half-hour drive).
On the way we stopped in Auburn, Indiana, a stop I particularly cared about to visit the Auburn Cord Duesenberg Automobile Museum.
The museum opened its doors in 1974 to safeguard the history of Auburn, Cord, and Duesemberg cars, inside what was the administrative headquarters of the Auburn Automobile Company from 1930 to 1937, when Auburn disappeared and the showroom and factory building served as a parts and restoration center for the brand’s obsolete cars until the 1960s, when the company was sold and the building fell into disuse. Fortunately, some people wanted to save the art deco building and the history of the Auburn-Cord-Duesemberg, and decided to restore the location and open the museum.
Right next to the museum, another must-see is the National Auto&Truck Museum, where our eyes sparkled! The museum has an incredible collection of American cars from every era, from the Golden Age to the present day. There even are some cars seen in movies, such as The Dukes of Hazzard or Back to the Future.
It is located, among other things, in a historic building built in the late 1920s that served as a factory for Cord and where the first 29 Cord 810, the first front-wheel drive car, was built.


The seventh day is spent getting a taste of Indianapolis: a visit to the Indianapolis Speedway Museum, a stroll down Massachussets Avenue and its murals, and on to nearby Monument Circle – from which the city gets its nickname – with its Soldiers and Sailors Monument. Finally, a nice dinner at Nevermore at Union Station, the pub dedicated to Edgar Allan Poe.
Day 8, on the road to Nashville: Santa Claus and Lincoln City, Indiana
From Indianapolis it takes about 4 1/2 hours to travel to Nashville, but it is a route full of things to see that and it takes the whole day. That is why we decided to leave Nashville only as a gateway city this time, dedicating it all the time it deserves on another trip.
First stop was the Jasper City Mill, Indiana, on the Patoka River. The current mill was finished in 2009 on the foundations of the previous one built in 1865 and torn down in 1964 after a flood, and that itself was a reconstruction of the first mill, dating back to 1815 and in which also a young Abraham Lincoln along with his father Thomas grinded grain.
Today it is still in operation and grinds corn and wheat to produce flour for sale. It can be visited and its interior contains memorabilia from the mill’s history.

Next stop is Santa Claus, Indiana, the town where Christmas is all year round. I couldn’t miss it!
Founded in 1849 under the name Santa Fe, the town soon needed to establish its own post office but the request was denied by the Post Office Department because there already was a Santa Fe in Indiana. The citizens had to get together to come up with a new name for the town and, according to legend, to solve this task they all gathered in a small wooden church on Christmas Eve. Several names were thrown around, but none seemed to be the right one. The children ran around playing while the adults argued. Suddenly, a gust of wind opened the church doors and the sound of many bells was heard, reminiscent of that of Santa’s sleigh. And so the name was decided without delay and was accepted by the Post Office Department.
Since this was the only post office in the world with this name, all the letters that children sent to Santa Claus were delivered here. In 1914 James Martin, the city’s 14th postmaster, began mailing reply letters from Santa at his own expense. An active tradition even today: anyone who writes to the post office will receive a reply letter from Santa Claus (even if you write and mail on the spot, as we did!).
Not only this: the world’s first Christmas themed park, the Santa Claus Land, was built here in Santa Claus, and the world’s first Christmas attraction opened in 1935: Santa’s Candy Castle, both of which are still open and active today.
There is so much more to say here, too, and I will tell you more about it!
Near Santa Claus is the Lincoln Boyhood National Memorial, a faithful reconstruction of the log house in the woods where Lincoln spent his childhood and adolescence (a reproduction of which can also be seen at the Lincoln Presidential Memorial in Springfield, Illinois), living here with his family from 1816 to 1830, when they moved to Illinois. Another small part of the itinerary on the places dedicated to the President who changed America.


Days 9, 10, 11: Memphis
Another city that I was looking forward to visit, from which I was very impressed and where I still have so much to see left… which is the perfect excuse to go back!
Memphis is a little over 3 hours away from Nashville and is the city of the Blues, Elvis, the Lorraine Motel, the Sun Studio, BBQ… and so much more! Three days is not enough to enjoy it to the fullest, but it is a good start.
On the first day, arriving at lunchtime, we went for lunch at the Arcade Restaurant, a Memphis icon: it is the oldest restaurant in town, opened in 1919, and Elvis’s favorite place to eat. It still maintains the typical 60s diner style, the food is great, and it also sells special beers from Beale St. Brewing Co, like the peanut&banana-flavored King’s Ransom!
Right after that we went to visit the Sun Studio, the mecca of music, a place that is a timeless legend. The thrill of being in there, the birthplace of rock and roll, is indescribable. To see original memorabilia from the golden years of music, to find yourself in the same spot where Elvis used to record, to be able to use one of their original microphones… little, big things that bring real emotions.
After a trip to Bass Pro Shop (a very American place I really wanted to see!), inside the famous Memphis pyramid, in the evening we walked down Beale Street, the home of the Blues, the most iconic street in America. Here it feels like stepping back in time, finding yourself in the midst of the 1950s-60s. Bright signs, neon, music from the clubs, murals… the symbols that make the vintage side of America so fascinating are all here. A street in which to walk down and up again, feeling the soul and living the beat… and eating the world’s best ribs at BB King Blues Club!


On the second day we visited Graceland, the home of Elvis Presley and probably the most famous place in Memphis. At Christmas time you can see it with the same decorations that the Presley family used. Each room is a narrative of their lives, from their most intimate and family moments and those on stage. On display are all of the awards Elvis won, his car collection, his clothes, two planes: The “Lisa Marie” and the “Hound Dog II”, and much more. The tale of a life of luxury and success that also concealed pain. At the end you visit the graves, always filled with flowers and small mementos left to the singer by the millions of fans who come by to say goodbye to him every year.
For lunch I recommend Central BBQ, great for enjoying the famous Memphis barbecue meat.
Afterwards we went to visit the Lorraine Motel, now the National Civil Rights Museum. This is the motel where Martin Luther King was shot and killed in on April 4, 1968, so it has since been transformed into the museum dedicated to the history of civil rights, leaving intact the room number 306 where King stayed and lost his life in. A visit to the museum is a journey through the history of African Americans, of their struggle to civil rights, to freedom. It is a journey that makes you feel involved, as only Americans know how to do, so much so that we suffer or rejoice along with the tale that unfolded – through images, testimonies, stories, relics and reconstructions – before our eyes.


On the last day before departure, we wanted to visit the Slave Haven Underground Railroad Museum, an important part of the Civil Rights Trail in Memphis. It is the home of Jacob Burkle, a German immigrant who was part of the antislavery movement and risked his life to help fleeing Africans, housing them in his home and helping them on their journey to freedom from 1855 until the abolition of slavery. The visit is very touching. The museum also tells about the journey from Africa to America and the conditions in which slaves were kept. One of the songs that the slaves sang in the camps is also sung, and there the emotion is really great, one girl was moved to tears.

Days 12 and 13: Springfield and Branson, Missouri
Leaving Memphis we began the drive up to Chicago. The first stop was Springfield, Missouri, and then taking Route 66 from there to Chicago.
From Memphis to Springfield it was the longest leg of the entire trip, just over 5 hours. Along the way we also stopped in Dyess, Arkansas, at a special place we couldn’t miss: the Johnny Cash Boyhood Home, the house where the Cash family moved in 1935 and Johnny stayed until 1950. Johnny’s songs have much about his life in Dyess. The original piano on which he learned to play can also be seen in the house. The house is a little gem to look at today, but living there was not easy: consider that the fields often flooded – which is why Arkansas is the largest producer of rice in the United States – and when that happened, the water would skim the entrance to the house and they couldn’t get out.
A beautiful place to see and full of things to learn, about Johnny and Arkansas.

Springfield is the birthplace of Route 66, in the sense that the name to be given to the road was decided here. Its downtown harkens back to the golden age of Route 66… and it is also home to the world’s largest fork, the Greetings from Springfield mural and the History Museum on the Square, which tells the story of Springfield from its founding to the present day. Each floor is dedicated to one or more different eras; there are many interactive spaces dedicated to children as well. Also displayed there is an award to Springfield native Tom Whitlock to celebrate the nine million records sold with his “Take my breath away”, the soundtrack to the first Top Gun.
In addition to downtown, linked to Route 66 is Roadside Park, and for food, you must try Red’s, which besides having great sandwiches, was America’s first drive-thru.
Springfield is also home to a section of the Trail of Tears, the road the Natives were forced to travel when they were driven from their land to Oklahoma.
For sleeping I recommend the Route 66 Rail Haven, a pure Route 66-style motel where Elvis himself slept!


From Springfield we also went to visit nearby Branson, or at least a small part of it. A town discovered thanks to relatives who live there, it is basically a huge amusement park. It has so many things to see or do, in fact we promised ourselves to return!
This time we came here to visit the Celebrity Car Museum, a museum where hundreds of cars taken from the movies are collected. Just the original ones used on set, driven by the actors (or their stuntmen)! My eyes sparkled in there, we looked like two kids at Disneyland. And the best thing is that by paying $10, you can get into one of the cars of your choice and have your pictures taken. A real thrill! There are not only cars but also memorabilia and objects taken from the sets. A must-see place – which I will tell you more about – for movie buffs!
Also in Branson is Silver Dollar City, a multi-award-winning theme park that, at Christmas time is illuminated by more than nine million lights, filled with light displays, parades and family fun.


Days 14 and 15: St. Louis
Leaving Springfield, we took Route 66 – which we had already traveled in the opposite direction – going through Lebanon, the Devil’s Elbow Bridge, Rolla, and Cuba to see things we had never seen and rediscover things we had already seen.
The first night in St. Louis we walked around a bit of its downtown, decked out for Christmas with lights and events. There is even a statue of Pinocchio!
The next day we strolled along the Old Chain Rocks Bridge, on Route 66, took a wonderful movie location tour – which I will tell you more about – which allowed us to discover a bit of the city, ate custard at Ted Drewes, climbed the Getaway Arch, which gives a wonderful view of Illinois and Missouri (for me the most beautiful one), and finally took a nice tour of the Budweiser Brewery, which at Christmas time is lit up by the Brewery Lights, a whole lot of lights, parades and Christmas attractions.


The next day we visited the National Blues Museum, where the roots of Blues music and all its evolution to the present day are told. I discovered so many beautiful new voices, interesting anecdotes and how important Blues music really is, the root of rock and pretty much all other genres. A really interesting place, full of information and stories, where you can even record, digitally, your own Blues song!

Immediately afterwards we left for Chicago, following Route 66 with stops in Livingston, Postville – where you can see the first Courthouse where Lincoln practiced as a lawyer – and Funks Grove, where Route 66’s only Maple Farm is located.
Day 16: Chicago
The last day is again devoted to Chicago. A suggestion on where to eat: try the Green Door Tavern, a pub dating back to 1872, believed to be the oldest tavern in Chicago, built just after the Great Chicago Fire and just before the law prohibiting the construction of wooden buildings in the city was enacted. In 1921 it became a speakeasy restaurant, which is why it had a green door. In the Prohibition era, the green color on the doors served to signal that a speakeasy was located inside the establishment.
Don’t miss their Turtle Cheesecake with caramel, chocolate and pecans.

Travel itinerary in the United States: useful information
This itinerary between the midwest and the southern United States, does not fit into the classic routes and has been carefully designed. There are about 3500 kilometers to be covered and to enjoy it even better, with more calm (with the possibility, for example, of also visiting Nashville and doing an extra night in Memphis and/or adding a visit to Tupelo, the city where Elvis was born), it would be perfect in twenty days – duration of the trip initially considered, then changed due to major force.
It could be shortened by going from Indianapolis directly to St. Louis, should you only have one week.
If you are interested in experiencing this wonderful trip, we can arrange it together.