It is possible to join a guided tour with your own motorcycle. The deduction is $100 per bike/per riding day (on this tour it would be a discount of $700 USD per bike) on the base tour rate. Furthermore, if you should break down the tour guides would not be allowed to work on your bike, nor would you be able to ride the spare bike of the trailer, due to insurance issues.
It is possible to join a guided tour with a rental car (convertible or other categories) - please ask for details.
After touching down at Chicago International Airport we ask you to transfer to your hotel. Chicago, it almost goes out with saying, is one hell of a town; the largest, most vibrant of the Great Lake cities. The city skyline has few peers and down on the streets you’ll find a fantastic selection of world class museums, restaurants and cafes. There is also the city’s famed bar and nightclub scene that is still anchored in an incredible jazz and blues tradition. The fun begins with a Welcome Dinner and drinks with your fellow riders, and ends in one of Chicago's finest hotels, The Drake. In the morning the long dreamt of journey across Route 66 begins.
First order of business is to pick up your Harley Davidson before you can start on the ultimate American road trip. Parallel to I-55, (the Interstate 55) the legendary Route 66 began its run right here. It cut through the state before it ran the whole way to the Pacific Coast. Along the way you’ll see old-time diners and service stations which are a real slice of Americana. Riding South from Chicago, we will pass the old archetypal truck stop town of McLean, but we don’t linger, instead we barrel through the coal-mining area of Illinois and continue along the Pontiac Trail, as this road used to be known. Finally we pull into Springfield, the Illinois state capital. You can choose between staying at either the Hilton Downtown Springfield or the historic Abraham Lincoln Hotel. Both hotels are just a stone’s throw from the site of Abraham Lincoln's Illinois home.
Making our way south, we head towards the state of Missouri on our way to St. Louis, a town rich in history. Along the way, we will pass through a number of Highway towns, which are great places for a stop en route. One thing’s for sure, you should see the famous Dixie truck stop, “Our Lady of the Highway Statue”, Litchfield and the “Ariston Café”. We will also set aside some time to visit Meramec Caverns as you head for the Mississippi River – a complex of mineral formations which are as rare as they are exquisite. And of course we couldn’t miss the famous “Chain of Rocks Bridge”. Now we are properly in Missouri, the state where the Mississippi River meets the Missouri River, and where you can find both forests meet the grassland prairies. It’s a short ride from the state border into the "Gateway to the West," St. Louis, a dynamic and cultured city nestled along the shores of the almighty Mississippi River. You will find not only some of the best live music, but also BBQ ribs in the entire United States in St. Louis. You can also study the magnificent St. Louis Arch from the window of tonight’s accommodations, the centrally located Hampton Inn.
It’s a nice idea to get up a little early before we hit the road. Take a short walk across the street and marvel at an early morning view of the St. Louis Arch and Mississippi River. Soon after we will have St. Louis in our rear view mirrors as we leave the city for the rolling Missouri hills. You will soon see why this is such a popular stretch for riders, especially after working up an appetite for a lunch stop at a place in the middle of nowhere that serves about the best darn BBQ you will ever eat! Tonight we stay in Joplin, a city still recovering from a massive tornado in 2011. We'll meet some of the locals in the downtown neighborhood and hear some hair-raising stories about how it felt to be in the eye of a deadly tornado!
Making tracks from Joplin we ride west through Oklahoma, following the contour of a landscape that feels as if it’s always been there. We cover 100 miles between Tulsa and Oklahoma City through what was known in the Old West as Indian country. In the 1830s this land, which was considered basically worthless, was set aside as Indian Territory. It became an expedient dumping ground for the so-called Five Civilized Tribes who had previously acted as a check on white settlement in the southern states. The Seminole of Florida, the Choctaw and the Chickasaw of Mississippi, and the Creek of Alabama were each assigned a share, and the rest was assigned to the Cherokee from Georgia, Carolina and Tennessee. The state still has a large Native American Indian population to this day. As you may or may not already know, “Oklahoma” is actually the Choctaw word for “red man”. As we head west we travel through El Reno and then ride over the mile-long bridge, near Bridgeport and straight into Oklahoma City. Be sure and enjoy your stay tonight in the heart and soul of Route 66 country! Your hotel is handily located in the Bricktown Neighborhood, which is packed with shops, restaurants and nightlife.
We get up nice and early for our trip into the Panhandle, the southernmost portion of the Great Plains. Frequently referred to as “the real Texas”, the Panhandle really lives up to the popular stereotype of how Texas is supposed to look. Where the buffalo once roamed and the indigenous peoples once lived was considered perilous and uninhabitable frontier country. However its value went up sharply during the 1870s as a source of natural resources - specifically Helium, especially in Amarillo, and oil. Together with agriculture, this brought enormous wealth to the region. Although Amarillo can seem cut off, even from the rest of Texas, it sits on one of the great American cross-country routes – the I-40 (once a part of legendary Route 66), roughly 300 miles from Albuquerque and 250 miles west of Oklahoma City. Home to a few of the world’s largest cattle ranches, Amarillo takes its name from Spanish and means “yellow”, the color so distinctive to this territory. The illustrious Ambassador Hotel in Downtown Amarillo will be our hosts this evening. Not only that but our good buddies from "The Big Texan Steakhouse" will pick everybody up at the hotel in a fleet of old Cadillacs with giant bull horns across the hood. On tonight’s menu are the finest steaks in the whole of Texas!
It’s time to bid a fond farewell to the Lone Star State. We’re on our way to “The Land of Enchantment”, that is New Mexico. After passing through the eccentric and colorful art installation known as Cadillac Ranch, we come to the highly atmospheric ghost town of Glen Rio, where you can stand with one foot in Texas and the other in New Mexico. At this stage of the trip, we have 5 states behind us and 3 still ahead. The ride continues through the land of Comanche Indians and into Tucumcari, the largest town between Albuquerque and Amarillo. Then we head up into the High Plains and the slightly dizzying altitudes of Santa Fe in central New Mexico. Santa Fe is one of the oldest and most picturesque cities in the United States. It will be our base for the following two nights, in a hotel just steps from the historic town square and mission, in the heart of Santa Fe’s Old Town.
Only a short ride left today to return our motorcycles. Please let us know if you need a day or two to enjoy the sights and many galleries Santa Fe offers!
What could possibly be better than riding Route 66 on a Harley-Davidson? Well, how about kicking off your Route 66 guided tour with two nights in Milwaukee to visit the Harley-Davidson Headquarters, and to enjoy a private, VIP experience at the Harley-Davidson Museum! This unique experience will be available to less than 50 riders per year. You will spend two nights in our Hotel right next to the Museum, you’ll visit the tiny shed where Mr. Harley and the Davidsons built their first motorcycles; all capped off by a one-of-a-kind Museum Experience. And if that’s not enough, you still have an incredible journey down The Main Street of America, Route 66, to look forward to. Route 66 in and of itself is the journey of a lifetime for most riders. Now, toss in a couple of days immersing yourself in the history, as well as the future, of Harley-Davidson, and you have the recipe for an unforgettable experience that will make you the envy of every rider on the planet.
We will grab a great breakfast at our hotel before making the short van trip to the H-D headquarters where we will be greeted by some of the Executives and Leaders of The Motor Company. We will then have the opportunity to shop in the H-D Corporate Store, an experience that is typically reserved for employees and partners. This is the only place in the world where you can purchase a Harley-Davidson t-shirt with “Juneau, Wisconsin,” the street the HQ sits on, as the location. It’s a pretty safe bet you will be the only person in your riding club, or even in your home city, that has the coveted “Juneau” t-shirt. Next we will make our way over to the H-D Museum for a truly VIP, behind the scenes experience. There is a lot to see in the Museum, so feel free to spend as much time as you like. It’s only a ten minute walk back to our accommodation.
2020 dates with the museum visit: May 12, June 23, Aug 11, September 8
2021 dates with the museum visit: May 11, June 22, Aug 10, September 7
1 rider 1 motorcycle 1 room: US$1,080.00, guided tours only
2 people 1 motorcycle 1 room: US$660.00 / per person, guided tours only
2 people 2 motorcycles 1 room: US$600.00 / per person, guided tours only
45 days or greater cancellation notice: No charge & refunded booking security deposit.
Cancellations received less than 45 days prior to the tour departure date will be subject to the following penalties:
44 -32 days cancellation notice: Up to 50% loss of total Tour Fee to cover hotel & other costs. Rental Voucher for the remaining amount for future travel.
31 days or less: Up to 100% loss of total Tour Fee. Rental Voucher for any remaining value for future travel.
Because of the chance of illness, accident, airline inefficiency, company insolvency or other unforeseen situations that may cause a customer (you) to miss a tour, we suggests to purchase travel/medical/health/trip cancellation insurance. It is a little expense that gives you piece of mind, highly recommended!
Motorcycle/car rental cancellation:
Package tour (vehicle rental + hotel reservations):
Various motorcycle insurances are available that you can book with your rental, for more information please have a look at our Insurance webpage.
To book this tour we need following information from you:
Date of best arrival to departure city (rental/riding starts next morning)
Rider(s): name, jacket size, home address, nationality, required insurance option(s): VIP Zero, VIP, SLI, selection of motorcycle model choice, room type: one or two beds in room? Any additional hotel rooms before or after the tour?
Pillion(s): name, jacket size, nationality
Booking deposit: $1,000 per motorcycle
Final payment: 6 weeks before tour commences
Payment method: wire transfer to our bank account. We also accept US personal checks (scanned to e-mail or mailed to our office).
PayPal and MoneyGram payments are not accepted
Please note: please do not purchase domestic/international airline tickets until tour is confirmed by us!