Route 66 Westbound (Self-Drive)

15 days
Difficulty Level
4000 km

Route 66 Westbound (Self-Drive)

Discover the allure of a Self-Drive Tour along the iconic U.S. Route 66, affectionately known as “The Mother Road.” This legendary highway has served as a pathway for migrants, dreamers, desperadoes, and countless vacationers venturing westward. During its heyday in the 1950s, Route 66 thrived, witnessing endless streams of cars journeying “bumper-to-bumper” to traverse the famed western migration route. This era saw the emergence of hotels, motels, and the blueprint of modern America. Today, much of Route 66 retains its original charm, with many of its roads, restaurants, gas stations, and nostalgic landmarks meticulously preserved as they were in the golden era of the ’50s. This makes Route 66 a paradise for motorcycle enthusiasts, offering a ride through time and a glimpse into the soul of America’s storied past.

Please note that this tour travels westbound, from Chicago to Los Angeles.


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: Arrival Chicago

After months of anticipation, the moment you’ve been waiting for has finally arrived: Welcome to Chicago! This vibrant city marks the beginning of an unforgettable journey, inviting you to explore its rich history, iconic architecture, and lively cultural scene.


Day 2: Chicago - Springfield

(Driving day 1: 307 km/187 miles)

This is the day you begin your Route 66 adventure! Once you’re geared up and ready on your bike, kick off your ride along the 4,000 km / 2,500-mile-long Historic Route 66. With Chicago fading into the distance behind you, you set out westward for a unique journey filled with history and excitement. Your first stop is Joliet, known as the home of the Blues Brothers. Then, it’s off to Wilmington to see “The Gemini Giant” and enjoy lunch.

Continuing along Route 66, you’ll pass by the old gas station at Odell, a prime example of the many vintage stations along the route, before reaching the museum in Pontiac. Finally, you’ll arrive in Springfield, your end stop for the day.


Day 3: Springfield - St.Louis

(Driving day 2: 179 km/111 miles)

Get ready for a day filled with classic Route 66 riding and stunning natural scenery. Your journey will take you through numerous villages, historic towns, and iconic Route 66 landmarks. Your first stop is Mt. Olive, home to an old Route 66 gas station steeped in history. From there, you’ll continue to Hamel, where you’ll take a break at a traditional Route 66 diner and bask in the sunshine.

As you continue your adventure, you’ll pass through several charming small towns before reaching St. Louis. Here, you’ll have the opportunity to cross the Mississippi River on the historic Chain of Rocks Bridge. Then, it’s time to visit one of the most renowned landmarks in the USA, “The Gateway Arch,” a monument dedicated to the pioneers who ventured westward. Visible from a distance of 6 km, the Arch serves as a symbol of exploration and adventure. Take a moment to capture the essence of the pioneers as you ride by the Arch, marking the end of your day’s journey. You’ll spend the evening in St. Louis, soaking in the atmosphere of this historic city.


Day 4: St.Louis - Springfield

(Driving day 3: 348 km/216 miles)

As you journey southwestward, you’ll be immersed in the breathtaking mountain vistas of the Ozarks, renowned for their scenic beauty along Route 66. Be sure to keep your camera at the ready to capture the stunning landscapes unfolding before you. Your first stop takes you to Stanton, where you’ll visit the Jesse James Museum in Meramec Mines. Here, you’ll have the unique opportunity to explore the caves where Jesse James and his gang once hid the loot from their infamous raids.

Continuing along the historic Route 66, you’ll traverse through the heart of the United States, encountering a diverse array of experiences and impressions that harken back to the road’s original heyday. Your journey brings you to the picturesque town of Cuba before continuing to Lebanon, where you’ll have the chance to admire the legendary Munger Moss Motel, an iconic landmark along Route 66. Finally, you’ll reach your destination for the day: Springfield, renowned as the hometown of President Abraham Lincoln.



Day 5: Springfield - Oklahoma City

(Driving day 4: 494 km/312 miles)

Continuing your adventure along the iconic Route 66, your first stop beckons at the renowned Gay Parita Sinclair, a traditional gas station steeped in Route 66 lore and managed solely through donations and sales of Route 66 memorabilia.

As you journey onward, you’ll pass through Joplin, catching sight of the welcoming sign for Kansas before crossing into the Sunflower State. Although your time in Kansas on Route 66 is brief, you’ll have the opportunity to visit notable landmarks like “4 Women on the Route” and the historic Marsh Rainbow Arch Bridge, each infused with a sense of nostalgia and history.

Upon entering Oklahoma, you’ll discover a state that has diligently preserved much of the original Route 66, offering a glimpse into the road’s storied past. Oklahoma’s landscape transitions from lush forests to arid terrain as you traverse its scenic byways. Along the way, you’ll make stops in vibrant towns like Tulsa, where you’ll visit the Route 66 Harley Davidson dealership, and Stroud, home to the iconic Rock Café.

Continuing through Oklahoma’s charming Route 66 towns, you’ll eventually reach your final destination for the day: Oklahoma City. Despite being the 31st largest city in the U.S. by population, Oklahoma City boasts an expansive land area, offering a fitting backdrop for the next chapter of your Route 66 journey.


Day 6: Oklahoma City - Amarillo

(Driving day 5: 427 km/267 miles)

After departing from Oklahoma City, your Route 66 adventure continues with a visit to Yukon. From there, you’ll journey onward to El Reno before making your way to Weatherford, entering the heart of cowboy country and the vast expanse of Texas.

As you traverse the prairie landscapes of Texas, you’ll encounter stretches of straight-line driving, offering a different perspective of the road. And what better way to experience Texas than with a hearty steak meal? Your first stop in Elk City includes a visit to the National Route 66 Museum, followed by a lunch break at a traditional Route 66 steakhouse in McLean. Here, you’ll savor one of the most tender steaks you’ve ever tasted, hand-selected by the owner to ensure the highest quality.

Continuing on to Amarillo, you’ll make several enjoyable stops, including Cavender’s Boot City to stock up on cowboy accessories. Upon arriving at your hotel and checking in, you’ll have the unique opportunity to experience a Route 66 legend: the Big Texan Steakhouse. Here, you can test your mettle by taking on the famous 72-ounce steak challenge. If you can finish the entire meal within 60 minutes—including the steak, baked potato, salad, shrimp cocktail, butter, and bread—you’ll earn the meal for free. It’s a challenge that many have attempted, but few have conquered. Are you ready to take on the challenge?


Day 7: Amarillo - Santa Fè

(Driving day 6: 451 km/280 miles)

Prepare for a hot day of driving through the expansive landscapes of cowboy country, where vast fields and open countryside stretch as far as the eye can see. While some parts of old Route 66 may no longer be drivable in this area, you’ll still get a taste of the iconic route as you journey through Texas and into New Mexico.

Your first stop of the day is the famous Cadillac Ranch, where you’ll have the opportunity to leave your mark on a unique work of art by signing one of the colorful vintage Cadillacs buried nose-down in the ground. From there, you’ll head to Adrian, known as the midpoint of U.S. Route 66, marking the halfway point of your journey to Los Angeles. Take a break at the local Midpoint diner for a cup of coffee before continuing into New Mexico.

As you make your way to Tucumcari, be sure to stop at the Blue Swallow Motel, renowned as one of the friendliest stops along Route 66. Enjoy lunch in Tucumcari before continuing your drive to Santa Rosa.

Your 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’s charming narrow streets and rich cultural heritage are sure to captivate you during your two-night stay, allowing you ample time to explore and immerse yourself in the unique atmosphere of this historic city.


Day 8: Santa Fè

(Explorer & fun day)
You have ridden over half of the distance on our Route 66 adventure and take a day off to recharge the batteries and enjoy more of the wonderful Santa Fe. The city is located high in the mountains; scenic “Sangre de Cristo “, and is rich in Spanish and Native American history and culture. A unique blend that can be seen in the local art and architecture.
You can relax by the pool, enjoy one of the many art galleries, explore Santa Fe or a guided city tour, or visit one of the town’s microbreweries. You can buy local art in the local market. Do not forget to try “The Green Chili Stew” which has become a favorite among our guests. Santa Fe’s cuisine is famous.

Day 9: Santa Fè - Gallup

(Driving day 7: 363 km/199 miles)

Today marks a transition from cowboy country to Indian native territory, promising an enriching journey through lands steeped in centuries of indigenous history and culture. Your day begins with a ride along scenic, winding roads to Madrid, a quirky and eclectic town situated on the historic Turquoise Trail. A former mining town, Madrid was reborn in the 70s and 80s as an art colony full of galleries, shops, and historic charm.

Continuing your route, you’ll venture just outside Albuquerque to the Route 66 Casino, where a delicious lunch awaits. From there, your journey leads you straight to Acoma Sky City, a sacred site of the Acoma Indians perched atop a majestic mesa. Accessible only by bus from the Acoma Museum, the holy city offers a profound glimpse into Native American spirituality and heritage. Remember to adhere to the guidance of your tour guide as you explore this revered location, and take advantage of opportunities to acquire authentic handmade Native American artwork.

As the day draws to a close, you’ll ride on to Gallup, concluding another day of adventure and cultural discovery along Route 66.


Day 10: Gallup - Williams

(Driving day 8: 390 km/244 miles)

Prepare for a day of desert landscapes and remarkable natural wonders as you journey through Navajo and Apache territory to the Petrified Forest and Painted Desert. Marvel at the fascinating sights of ancient petrified wood and the vibrant hues of the painted sands, creating a surreal and unforgettable experience. As you traverse through this stunning nature reserve, be sure to capture memories that will last a lifetime.

Next, your route takes you to Holbrook and Winslow, where you’ll have the opportunity to stop at the iconic “corner” immortalized in the lyrics of the Eagles’ famous song. Take a moment to soak in the atmosphere and perhaps enjoy a delicious lunch in Winslow.

Following your break, continue along Route 66 to Williams, a vibrant destination known for its captivating charm. Here, you’ll enjoy a fun-filled evening, soaking up the unique ambiance of this iconic Route 66 stopover. Get ready for a night to remember in Williams!


Day 11: Williams - Grand canyon - Kingman

(Driving day 9: 433 km/271 miles)

Today marks a pinnacle moment of your tour as you welcome the awe-inspiring Grand Canyon into your itinerary. Your journey commences with a thrilling ride through the winding roads of Oak Creek Canyon, offering a blend of fun and challenge en route to this natural wonder. Passing through Flagstaff and tracing Historic Route 66, anticipation builds until you arrive at the Grand Canyon, a sight promising to be a highlight of your adventure.

Upon reaching the Grand Canyon, If you have pre-ordered the helicopter tour, you will embark on an experience that you will never forget. Soaring high above one of the world’s seven wonders for a unique perspective of its breathtaking beauty.

Following the exhilarating helicopter tour, you explore Grand Canyon National Park, immersing yourself in its grandeur. Marvel at panoramic vistas, deep gorges, and mesmerizing colors that have captivated visitors for centuries. After departing the Grand Canyon, you journey to charming Seligman, a traditional Route 66 town with abundant photo opportunities. The day continues with desert driving, hot conditions, and scenic views, punctuated by a stop at Hackberry, a historic gas station straight out of an old movie, where you enjoy a refreshing treat in the shade before cruising to Kingman, another pivotal city on the route.


Day 12: Kingman - Las Vegas

(Driving day 10: 229 km/143 miles)

Begin your day with a breathtaking drive to Oatman, a historic western village nestled in Mohave County. Established by gold prospectors in 1915, the journey to Oatman features narrow, winding roads amidst stunning mountain and desert landscapes, offering prime filming opportunities. Upon arrival, be sure to secure your bikes and keep an eye out for roaming donkeys and “outlaws” on the streets.

Continuing along Route 66, your next destination is the vibrant city of Las Vegas, known as “The Adult Playground” or “Sin City”. Las Vegas offers an array of entertainment options, from stunning buildings to unique shows and world-renowned casinos. Explore iconic landmarks such as Caesars Palace, Bellagio, MGM, and The Venetian, or witness captivating attractions like the volcanic eruptions at the Mirage and the mesmerizing water show at the Bellagio. Las Vegas promises an unforgettable experience with endless excitement and endless possibilities.


Day 13: Las Vegas - Big Bear Lake

(Driving day 11: 352 km/219 miles)

Prepare for a day of diverse driving experiences, spanning city streets, highways, and desert landscapes, with temperatures soaring. To combat the heat, we advise wearing a hydration (cooling) vest for added comfort. Begin your day with breakfast and a drive along the iconic Las Vegas Strip, followed by a group photo opportunity at the renowned “Welcome to Las Vegas” sign.

Continuing towards Los Angeles, make a stop at Calico Ghost Town for a glimpse into the Old West before enjoying lunch in Barstow. Afterward, journey to the picturesque vacation destination of Big Bear Lake, where you’ll savor your final evening on the road, surrounded by enchanting scenery and lasting memories.


Day 14: Big Bear Lake - Los Angeles

(Driving day 12: 253 km/157 miles)

Your tour concludes with an unforgettable ride along one of the United States’ premier motorcycle roads: the Angeles Crest Highway (CA-2). This final journey promises to be a highlight, offering magical routes and spectacular vistas that will etch this experience into your memory. The breathtaking scenery and exhilarating curves of the Angeles Crest Highway are perfect for those who love the thrill of the ride and the beauty of nature.

Be sure to take advantage of the numerous opportunities to stop and capture the stunning scenery with your fully charged cameras. This will truly be a once-in-a-lifetime experience.

As you make your way back to Los Angeles, the sense of accomplishment and the joy of having traversed one of the most iconic roads in the country will accompany you. Upon returning your bike and checking into your hotel, you’ll have the chance to reflect on the incredible experiences and the unforgettable routes that have marked this Historic Route 66 adventure.


Day 15: Departure - Home Travel

As you check out of the hotel and board the shuttle bus to the airport, your journey on the Route 66 Self-Drive Tour comes to a close. This adventure has taken you across landscapes filled with history, beauty, and the spirit of the open road. We hope that the miles you’ve traveled have brought you unforgettable experiences, scenic wonders, and a deeper appreciation for the legendary path that is Route 66.

Thank you for choosing our Route 66 Self-Drive Tour. It has been our pleasure to guide you through this iconic journey, and we hope that the memories you’ve made will be cherished for a lifetime. Safe travels home, and we look forward to welcoming you on another adventure in the future.

Please note: Due to time differences, travelers from Europe will arrive home on the date or day after departing from the US.

Additionally: It’s essential to understand that while our itinerary outlines a comprehensive framework for the tour’s planned activities and experiences, deviations may occur. The beauty of a self-drive tour lies in the personal freedom it offers. You are in control, serving as your own guide. This flexibility allows you to choose whether to stick to our suggested path or venture off into detours that catch your eye. Your adventure is yours to shape, providing an opportunity to make the trip uniquely yours, filled with unexpected discoveries and personal highlights.