Historic Route 66

15 days
Difficulty Level
4000 km

Historic Route 66

Explore the enchanting journey of Historic Route 66, renowned as “the mother road,” whether you’re heading westbound or eastbound. This iconic road trip presents an array of compelling reasons to embark on this adventure:

  1. Rich Historical Legacy: Route 66 is steeped in history, embodying the American spirit of exploration and adventure. Originally one of the nation’s primary highways, it linked Chicago to Los Angeles, serving as a vital route for migrants and travelers during the 20th century.
  2. Nostalgic Americana: Traveling along Route 66 leads you to a multitude of classic roadside attractions, vintage motels, and retro diners. Immerse yourself in the charm and allure of mid-century America.
  3. Stunning Scenic Beauty: This route winds through diverse landscapes, unveiling the breathtaking beauty of the American Southwest. From rolling plains to rugged mountains, it showcases some of the country’s most picturesque vistas.
  4. Cultural Odyssey: Route 66 offers the chance to immerse yourself in various regional cultures as you traverse different states, each with its unique traditions, art, and cuisine.
  5. Quirky Roadside Delights: The journey is punctuated with eccentric and captivating roadside attractions, such as the Cadillac Ranch in Texas or the Wigwam Village Motels in Arizona, making your adventure both entertaining and unforgettable.
  6. Personal Milestone: Completing this epic cross-country road trip represents a significant personal achievement. Conquer a historic and legendary route that has captured the imaginations of countless travelers over the years.


Motorcycle/Car rental w/unlimited milage
1st choice vehicle model class
Shared room in biker-friendly hotels
Continental breakfast at most hotels
Entrance fees Nat. parks
Welcome meeting
Multi-lingual Tour leader
Transport to rental company
Support van w/ luggage
State min. SLI insurance
Loss damage Waiver
Half-shell helmet
Tour PDF w/route description.
Pictures from the tour
NOT Included
Optional attractions
Vehicle model guarantee
Security deposit for LDW
Food and beverages
LDW Zero & insurance upgrades
Anything not listed in “Included” above



Day 1: Departure - Arrival Chicago

The eagerly anticipated departure day has arrived at last: Welcome to Chicago!

As all tour participants arrive, we’ll gather for a warm reception and refreshments. This evening is dedicated to making connections and getting to know each other better. If you’re still energized after your journey, there’s an option to relax at a local bar nearby for more socializing and shared experiences.


Day 2: Chicago - Bloomington, Il

(Driving day 1: 212 km/132 miles)

Today marks the beginning of our much-anticipated Route 66 adventure! Once everyone is ready, we’ll set out on our journey along Historic Route 66. Chicago will slowly fade into the distance as we head west, promising a unique adventure filled with history and enjoyment.

Our first stop is Joliet, home to the Blues Brothers, setting the stage for a musical and cultural experience. Next on our route is Wilmington, where we’ll encounter “The Gemini Giant” and enjoy a delightful lunch.

Continuing on Route 66, we’ll pass by the historic gas station at Odell, a prime example of the day-open stations that once lined this iconic highway. Our exploration will take us to the museum in Pontiac before concluding in Bloomington, our destination for the day and a testament to Route 66’s rich legacy. Get ready for a day filled with history, fun, and the open road!


Day 3: Bloomington - St.Louis, Mo

(Driving day 2: 273 km/170 miles)

Prepare for a day brimming with the timeless charm of Route 66 and breathtaking encounters with nature. Our route will take us through numerous villages, historic towns, and Route 66 landmarks. Our first stop is Springfield, the hometown of Abraham Lincoln, adding historical richness to our journey.

Continuing our adventure, we’ll head to Mt. Olive, home to the Soulsby old Route 66 gas station. Next on our route is Hamel, where we’ll take a refreshing break at a traditional Route 66 diner, enjoying the warmth of the sun.

As we pass through several small towns, the grandeur of St. Louis awaits. Crossing the mighty Mississippi River on the historic Chain of Rocks bridge, we’ll make a stop at one of the USA’s most iconic landmarks—the “Gateway Arch,” a tribute to the pioneers who ventured west. Visible from 6 km away, the Arch serves as a symbolic milestone. Following the path of the pioneers, we’ll ride by the Arch, pausing to capture the significance of the moment. The evening will unfold in St. Louis, offering an opportunity to soak in the rich history and vibrant atmosphere of this city on the banks of the Mississippi.


Day 4: St.Louis - Springfield, Mo

(Driving day 3: 372 km/231 miles)

Our journey continues in the stunning southwest, traversing the mesmerizing mountain landscapes of the Ozarks—a breathtaking spectacle along Route 66. Keep your cameras ready to capture the beauty of this scenic stretch!

Our first stop takes us to Stanton and the Jesse James Museum in Meramec Mines, offering a unique opportunity to explore the caves where Jesse James and his gang hid their spoils from infamous raids.

Venturing through the heart of the United States, we’ll follow the original path travelers took on Route 66, brimming with diverse experiences and impressions. Our next destination is the picturesque town of Cuba, setting the stage for a charming encounter with the essence of this iconic route. We’ll then proceed to Lebanon, where the legendary Munger Moss Motel awaits our exploration.

Our final stop for the day is Springfield, a city steeped in history as the home of President Abraham Lincoln. As we conclude this leg of our journey, reflect on the tales of the past and anticipate the adventures that lie ahead on the storied road of Route 66.


Day 5: Springfield - Oklahoma City, Ok

(Driving day 4: 494 km/312 miles)

Our adventure continues along the captivating stretches of Route 66. Our first destination is the renowned Gay Parita Sinclair, a traditional gas station sustained solely through donations and the sale of Route 66 memorabilia—a testament to the kindness of Gary Turner, known as the kindest man on Route 66. As we move forward, we’ll pass through Joplin, where a welcoming “Welcome to Kansas” sign greets us.

The Kansas leg of our journey is brief, covering approximately 31 km. Our stops include the famous “4 Women on the Route” and the Marsh Rainbow Arch Bridge, both brimming with historical charm. Entering Oklahoma, a state that has admirably preserved much of the original Route 66 (spanning about 633 km), we’ll notice the landscape transitioning from lush greenery to a drier environment. Oklahoma holds the distinction of being the state where the term “The Mother Road” originated, and locals predominantly use Route 66 due to tolls on Interstate 44.

Riding through the beautiful and verdant landscapes of Oklahoma, we’ll make several noteworthy stops, including Tulsa, where we’ll visit the Route 66 Harley Davidson, and Stroud, home to the iconic Rock Café.

Our journey continues, weaving through numerous small, charming Route 66 towns before reaching our final stop for the day: Oklahoma City.


Day 6: Oklahoma City - Amarillo, Tx

(Driving day 5: 427 km/267 miles)

Having immersed ourselves in the allure of Oklahoma City, our Route 66 odyssey presses on. Our next destination is Yukon, the hometown of the renowned country music artist Garth Brooks. From there, we journey to El Reno before setting our sights on Weatherford.

Transitioning into cowboy country and the vast expanse of Texas, our route takes us through prairie landscapes, featuring some straight-line stretches. Appropriately, this day is also designated as “the steak” day, promising a culinary delight.

Our initial stop is Elk City, where we’ll explore the National Route 66 Museum and capture moments in front of the iconic Route 66 sign. En route to Amarillo, we’ll make a pit stop in McLean at a traditional Route 66 steakhouse for a delectable lunch. The establishment, known for its tender steaks, personally sources all beef to ensure the highest quality.

Upon reaching Amarillo, we’ll embark on a series of enjoyable stops, including Cavender’s Boot City, where we can stock up on cowboy accessories.

Following check-in at the hotel, we’ll visit a Route 66 legend—the “Big Texan Steakhouse.” Here, the renowned 2.2 kg (72 oz.) steak awaits, and those daring enough to finish the entire meal within 60 minutes (including the steak, baked potato, salad, shrimp cocktail, butter, and bread) earn the meal for free. A challenge attempted by many, conquered by a select few. Are you ready to take on the legendary Big Texan Steakhouse challenge?


Day 7: Amarillo - Santa Fè, Nm

(Driving day 6: 451 km/280 miles)

Prepare for a sun-soaked journey through the expansive landscapes of cowboy country, featuring long stretches of flat fields and countryside. Our route may include sections on I-40, as some parts of the old Route 66 are no longer drivable in this area.

Our first noteworthy stop is the iconic “Cadillac Ranch,” where you have the opportunity to leave your mark on a unique work of art. We then proceed to Adrian, home to the “Midpoint U.S. Route 66,” marking the halfway point on our journey to Los Angeles. A stop at the local Midpoint diner for a cup of coffee precedes our exit from Texas and entry into New Mexico.

Continuing our adventure, we arrive in Tucumcari, where a visit to the friendly “Blue Swallow” motel awaits. Lunch in Tucumcari fuels us for the drive to Santa Rosa.

Our final destination for the day is Santa Fe, hailed as one of the most beautiful cities in the western United States and the capital of New Mexico. Santa Fe will graciously host us for the next two nights. Within minutes of navigating Santa Fe’s narrow streets, you’ll find yourself enamored with the city and its welcoming population. Get ready to fall in love with the charm of Santa Fe!


Day 8: Santa Fè

(Explorer & fun day)

Reaching the midpoint of our Route 66 journey, we pause in Santa Fe for a day of rejuvenation and exploration. Surrounded by the majestic mountains and the picturesque Sangre de Cristo range, Santa Fe is a city where Spanish and Native American histories intertwine, presenting a captivating mix of art and architectural marvels.

The day is yours to enjoy in any way you prefer. Unwind by the pool, wander through the art galleries, take a city tour, or check out the local microbreweries. Make sure to visit the local markets for unique art finds and taste the acclaimed Green Chili Stew, a culinary highlight.

Evening brings a cowboy dining experience in a traditional setting, offering a taste of the authentic cowboy lifestyle with great food and company.


Day 9: Santa Fè - Gallup, Nm

(Driving day 7: 367 km/226 miles)

Today, we transition from the cowboy heartlands to the deeply rooted territories of Native American heritage, promising a day filled with cultural discovery and scenic beauty. We start our journey on the quaint, meandering roads to Madrid, a town that has risen from its past as a deserted coal mining locale to become a flourishing artistic hub, home to over 40 unique shops and galleries, various eateries, a spa, and a museum.

After soaking in the charm of Madrid, we’ll venture towards Albuquerque, stopping at the Route 66 Casino for a savory lunch. Next, our path leads us to Acoma Sky City, the sacred city of the Acoma Indians, situated on a towering mesa. Upon arrival, we’ll gather at the Acoma Museum to get our tickets and board a bus that will take us up to the city, as individual ascent is not allowed. Atop the mesa, we’ll stick together, following our guide closely, while having the chance to collect distinctive, handcrafted Native American art pieces.

As we journey through these captivating landscapes and delve into the profound cultural heritage, our day culminates with our arrival in Gallup, a reflection on the rich traditions and history of the native lands we’ve explored.


Day 10: Gallup - Williams, Az

(Driving day 8: 390 km/244 miles)

Prepare for a journey through the desert landscapes, where natural marvels await. Starting in the vast territories of the Navajo and Apache, our path takes us to the Petrified Forest and the Painted Desert, where nature blurs the lines between stone and wood, and colors paint the sands. This stretch of our adventure is sure to etch lasting memories.

Next, we make our way to Holbrook and Winslow, taking a moment at the famed corner that Eagles fans will recognize from the song lyrics, “Standing on a corner in Winslow, Arizona.” A lunch stop in Winslow offers a welcome break to recharge.

Replenished, we proceed along Route 66 to Williams. Known as one of the route’s most engaging stops, Williams invites us to a night of entertainment and discovery, embodying the spirit of this historic highway.


Day 11: Williams - Grand canyon - Kingman, Az

(Driving day 9: 433 km/271 miles)

Today marks a highlight of our tour with a visit to the Grand Canyon. Our day starts at the Grand Canyon Visitor Center, where we’re treated to the world’s most popular IMAX movie, offering an immersive experience akin to exploring the canyon itself. Following this, we venture into the Grand Canyon for unforgettable photo opportunities.

Please remember, that helicopter tours require pre-booking.

Leaving the Grand Canyon behind, we head to Seligman, a town that proudly preserves the essence of Route 66. Seligman’s inviting atmosphere offers plenty of chances for memorable photographs. The day continues with a scenic drive through the desert, featuring a stop at Hackberry’s nostalgic Route 66 gas station for a cool break. Our journey concludes in Kingman, a key landmark along Route 66, rounding off a day filled with iconic sights and experiences.


Day 12: Kingman - Las Vegas, Ne

(Driving day 10: 229 km/143 miles)

Start the day with a scenic drive to Oatman, a historic mining village set in the heart of Mohave County, established by prospectors in 1915. This route to Oatman, characterized by its narrow and serpentine roads that climb and descend through diverse terrains, presents breathtaking views of both mountainous and desert landscapes, offering a truly picturesque journey. Upon arrival in Oatman, remember to secure your bikes and watch for the local donkeys and actors dressed as outlaws adding to the town’s old-west charm.

The journey continues on Route 66 to the vibrant city of Las Vegas, a place known for its endless entertainment possibilities. Dubbed “The Adult Playground” and “Sin City,” Las Vegas is a bustling metropolis where architectural marvels, spectacular shows, top-tier casinos, and a wide array of entertainment choices await. The city’s energy is palpable, promising an exciting and dynamic experience at every turn.

Make sure to visit renowned landmarks like Caesars Palace, Bellagio, MGM Grand, and The Venetian, among others. Highlights include the Mirage’s volcanic eruption show and the Bellagio’s famous water fountains, offering unforgettable sights. Las Vegas is a city of endless discovery, promising new adventures around every corner.


Day 13: Las Vegas - Big Bear Lake, Ca

(Driving day 11: 352 km/219 miles)

Today’s journey offers a mix of urban and natural landscapes, from bustling city streets to the tranquility of the desert. To combat the desert heat, we suggest wearing a hydration vest. After enjoying breakfast, we’ll drive down the Las Vegas Strip for a group photo at the iconic “Welcome to Las Vegas” sign, capturing a memorable moment.

Our path then takes us toward Los Angeles, with a stop at the intriguing Calico Ghost Town, followed by lunch in Barstow, a town rich in history. The day’s drive culminates at Big Bear Lake, a picturesque alpine setting where we’ll spend our final evening. Prepare to be captivated by the serene beauty of Big Bear Lake, rounding off our journey with lasting memories of this exceptional adventure.


Day 14: Big Bear Lake - Los Angeles, Ca

(Driving day 12: 248 km/154 miles)

Our final day brings us to an exciting climax with a ride along the Angeles Crest Highway (CA-2), celebrated as one of the premier motorcycle routes in the United States. This journey offers a thrilling experience as we navigate through enchanting landscapes, capturing views that will leave a lasting impression. Make sure your cameras are ready to document this unparalleled ride.

The route includes planned stops to take in the breathtaking vistas before we head towards Los Angeles. Upon arrival and after returning our bikes, we’ll mark the conclusion of our epic journey with a visit to Santa Monica Pier, the historic end of Route 66, where we’ll celebrate our shared adventure.


Day 15: Departure - Home Travel

As we depart from our hotel, a shuttle will be ready to take you to the airport for your journey home. We’re grateful for the opportunity to have shared this extraordinary experience with you and cherish the memories we’ve created together.

Note: Due to the time difference, travelers from Europe will arrive home on the date/day following their departure from the US.

Kindly note that this program serves as a comprehensive guide for the activities and experiences on the tour. While occasional deviations may occur, we assure you that our dedicated tour leaders will exert every effort to execute the program as described, to the best of their ability and by prevailing circumstances. We are committed to ongoing improvements, so be prepared for positive surprises throughout your journey with us. Safe travels and we hope to welcome you back for more adventures!

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Historic Route 66