Historic Route 66, Westbound & Eastbound.
Riding Historic Route 66, affectionately known as “the mother road,” is an exceptional journey that offers several compelling reasons to embark on this iconic road trip:
Rich Historical Significance: Route 66 is steeped in history, representing the American spirit of adventure and exploration. It was one of the original highways in the U.S., connecting Chicago to Los Angeles and serving as a vital route for migrants and travellers during the 20th century.
Nostalgic Americana: As you Ride along Route 66, you’ll encounter an array of classic roadside attractions, vintage motels, and retro diners, taking you back to experience the charm and allure of mid-century America.
Breathtaking Landscapes: The road winds through diverse landscapes, showcasing the stunning beauty of the American Southwest. You’ll witness some of the country’s most picturesque vistas, from rolling plains to rugged mountains.
Cultural Immersion: Route 66 allows you to immerse yourself in various regional cultures as you pass through different states, each with unique traditions, art, and cuisine.
Quirky Roadside Stops: The route is dotted with quirky and fascinating roadside attractions, like the Cadillac Ranch in Texas or the Wigwam Village Motels in Arizona, making the journey entertaining and memorable.
Personal Achievement: Completing this epic cross-country road trip can be a significant personal achievement as you conquer a historical and legendary route that has captivated the imaginations of countless travellers over the years.
In summary, Riding Historic Route 66 is an unparalleled opportunity to connect with America’s past, experience its diverse landscapes and cultures, and create lasting memories that celebrate the essence of the open road.
| DEPARTURE / RETURN LOCATION | Chicago / Los Angeles or Los Angeles / Chicago |
Map –
ITINERARY WESTBOUND
Day 01: Departure – Arrival Chicago
Tomorrow marks the beginning of your long-awaited departure day as you arrive in Chicago. Upon landing at the Chicago airport and collecting your luggage from baggage claim, exit the arrival hall to the traffic island with the “red” sign labelled “Hotel and Courtesy Shuttles.” Look for a mini-bus with the hotel name, conveniently close to the airport, offering a free shuttle bus service every 30 minutes. One of our friendly tour guides will greet you at the hotel reception. Please note that check-in at the hotel is not allowed until 3 PM (15:00).
After all tour participants have arrived in the evening, we will gather for a welcome reception and refreshments, introducing everyone and kicking off the program designed to get to know each other. Visiting a local bar nearby is an option for those still full of energy after the journey.
Day 02: Chicago – Bloomington, IL (Riding day 1: 212 km/132 miles)
The following day is the commencement of our Route 66 adventure! We embark on the 2,600-mile-long Ultimate Route 66 tour as everyone gets ready on their bikes. Chicago fades into the background as we head west for an adventure of history and fun. Our journey takes us to Joliet, home of the Blues Brothers, and then to Wilmington with “The Gemini Giant,” where we’ll have lunch. Riding Route 66, we pass the old gas station at Odell before visiting the Pontiac Museum and finally reaching Bloomington, our end stop for the day.
Day 03: Bloomington – St. Louis, MO (Riding day 2: 273 km/170 miles)
The next day promises traditional riding on Route 66 and spectacular nature. We’ll explore many villages, ancient towns, and historic Route 66 landmarks. Stops include Springfield, Abraham Lincoln’s home town, Mt. Olive, the Soulsby old Route 66 gas station, and a break in Hamel at a traditional Route 66 diner. We then journey to St. Louis, crossing the Mississippi River on the historic Chain of Rocks bridge, stopping at “The Gateway Arch,” and spending the evening capturing the spirit of this iconic city.
Day 04: St. Louis – Springfield, MO (Riding day 3: 372 km/231 miles)
We continue southwest through the stunning mountain scenery of the Ozarks along Route 66, with a stop at Stanton and the Jesse James Museum in Meramec Mines. Our adventure takes us through the heart of the United States, with picturesque Cuba, Lebanon, and a look at the legendary Munger Moss Motel in Springfield, the home of President Abraham Lincoln, being our final stop for the day.
Day 05: Springfield – Oklahoma City, OK (Riding day 4: 494 km/312 miles)
Continuing along exciting Route 66, we visit the famous “Gay Parita Sinclair” gas station, Ride through Kansas, and stop at the “4 Women on the Route” and Marsh Rainbow Arch Bridge. Passing through Tulsa, Stroud, and the Rock Café, we enjoy Oklahoma’s beautiful and lush scenery before reaching our final stop for the day: Oklahoma City, the 31st largest city in the U.S.
Day 06: Oklahoma City – Amarillo, TX (Riding day 5: 427 km/267 miles)
After experiencing Oklahoma City, we continued our Route 66 adventure, passing through Yukon, El Reno, and Weatherford, moving into Cowboy Country and Texas. Stops include Elk City for the National Route 66 Museum, McLean for a traditional Route 66 steakhouse lunch, and Cavender’s Boot City in Amarillo. The day ends with a visit to the “Big Texan Steakhouse,” where the challenge of the famous 2.2 kg (72 oz.) steak awaits.
Day 07: Amarillo – Santa Fe, NM (Riding day 6: 451 km/280 miles)
It’s a hot Riding day in cowboy country, featuring a visit to the famous “Cadillac Ranch” and a stop at Adrian, the midpoint of U.S. Route 66. Riding into New Mexico, we pass through Tucumcari, visit the “Blue Swallow,” and continue to Santa Fe, one of the most beautiful cities in the western United States. Santa Fe will be our home for the next two nights.
Day 08: Santa Fe (Explorer and fun day)
Having covered over half the distance on our Route 66 adventure, we take a day off to recharge and further explore the wonders of Santa Fe. The city, situated high in the mountains with scenic views of “Sangre de Cristo,” is rich in Spanish and Native American history. The day is yours to use, whether relaxing by the pool, visiting art galleries, exploring Santa Fe on a guided city tour, or enjoying the local cuisine. The evening includes visiting a real cowboy restaurant to savour steak and experience the authentic cowboy way of life.
Day 09: Santa Fe – Gallup, NM (Riding day 7: 367 km/226 miles)
Leaving cowboy country, we enter Indian native territory with a visit to Madrid, known for the “Wild Hogs” movie. Our journey continues to the Route 66 Casino near Albuquerque, then to Acoma Sky City, the Acoma Indians’ holy city. The day concludes with a Ride to Gallup.
Day 10: Gallup – Williams, AZ (Riding day 8: 390 km/244 miles)
This day brings desert Riding and unique nature, including a visit to the Petrified Forest and the Painted Desert in Navajo and Apache territories. Stops at Holbrook, Winslow, and the “corner” precede our arrival in Williams, one of the coolest destinations on Route 66, where we’ll spend a fun night.
Day 11: Williams – Grand Canyon – Kingman, AZ (Riding day 9: 433 km/271 miles)
A highlight awaits us as we journey to the Grand Canyon. After experiencing the Grand Canyon’s Visitor Center and watching the world’s most-viewed Imax movie, we ride into the Grand Canyon to capture this year’s holiday photo. The day continues with stops in Seligman, Hackberry, and Kingman, featuring desert Riding, scorching conditions, and stunning scenery.
Day 12: Kingman – Las Vegas, NV (Riding day 10: 229 km/143 miles)
Starting with a spectacular Ride to Oatman, an old western town, we continue Route 66 to Las Vegas, “The Adult Playground” or “Sin City.” Las Vegas offers everything from stunning buildings to unique shows, casinos, and entertainment. Enjoy the city’s vibrant atmosphere, and take in the sights of famous landmarks.
Day 13: Las Vegas – Big Bear Lake, CA (Riding day 11: 352 km/219 miles)
A day of city, highway, and desert Riding awaits, featuring a ride along the strip and a group photo in front of the famous “Welcome to Las Vegas” sign. Heading towards Los Angeles, stops include Calico Ghost Town and lunch in Barstow. The day concludes at the beautiful vacation resort, Big Bear Lake, for our last magical evening on the road.
Day 14: Big Bear Lake – Los Angeles, CA (Riding day 12: 248 km/154 miles)
We conclude our tour with a spectacular ride on one of the U.S.’s best motorcycle roads: the Angeles Crest Highway (CA-2). This breathtaking riding experience offers spectacular views, making it a once-in-a-lifetime experience. After several stops and a memorable ride on Angeles Crest Highway, we head towards Los Angeles, return our bikes, and check into the hotel. The day concludes with a visit to Santa Monica Pier, the end of Historic Route 66, and our farewell party.
Day 15: Departure – Travel Home
Checking out of the hotel, we catch a shuttle bus to the airport for our journey home. Thanks for a great ride and good times, and we sincerely appreciate your choice to travel with us. Note: Due to the time difference, travellers from Europe will arrive home on the date/day after departing the US. This program serves as a guideline, and while deviations may occur, our positive tour leaders will strive to execute the program as described to provide positive surprises along the way.
Tours.
| Tour | Date from | Date to | Booking deadline |
| Route 66 Westbound | 19-May-25 | 2-Jun-25 | 19-Apr-25 |
| Route 66 Westbound | 15-Jul-25 | 29-Jul-25 | 15-Jun-25 |
| Route 66 Westbound | 21-Sep-25 | 5-Oct-25 | 21-Aug-25 |
| Route 66 Westbound | 19-May-26 | 2-Jun-26 | 19-Apr-26 |
| Route 66 Westbound | 14-Jul-26 | 28-Jul-26 | 14-Jun-26 |
| Route 66 Westbound | 22-Sep-26 | 6-Oct-26 | 22-Aug-26 |
ITINERARY EASTBOUND IS THE REVERSE OF THE ABOVE ITINERARY.
Please note that we reserve the right to remain adaptable to unforeseen circumstances and weather conditions that may arise while on tour; the daily schedule may be adjusted accordingly. The client’s tour remains paramount; we will ensure the tour meets your fullest expectations.
| Tour | Date from | Date to | Booking deadline |
| Route 66 Eastbound | 4-May-25 | 18-May-25 | 4-Apr-25 |
| Route 66 Eastbound | 1-Jul-25 | 15-Jul-25 | 1-Jun-25 |
| Route 66 Eastbound | 6-Oct-25 | 20-Oct-25 | 6-Sep-25 |
| Route 66 Eastbound | 3-May-26 | 17-May-26 | 3-Apr-26 |
| Route 66 Eastbound | 29-Jul-26 | 12-Aug-26 | 29-Jun-26 |
| Route 66 Eastbound | 7-Oct-26 | 21-Oct-26 | 7-Sep-26 |
Prices (USD)
2 people / 1 vehicle / 1 shared room: From $4,495.00 per person
2 people / 2 vehicles / 1 shared room: From $5,995.00 per person
1 person / 1 vehicle / 1 single room: From $7,570.00 per person
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Inclusions and Exclusions.
| INCLUDED | Motorcycle/Car rental with unlimited mileage 1st choice vehicle model class Shared rooms in biker-friendly hotels Continental breakfast at most hotels National Park Entrance fees Welcome meeting Multi-lingual Tour leader Transport to rental company Support van State min. SLI insurance Loss damage Waiver Half-shell helmet Tour route descriptions Pictures from the tour |
| NOT INCLUDED | Airfare Optional attractions Vehicle model guarantee Fuel Security deposit for LDW Food and beverages LDW Zero & insurance upgrades Anything not listed in “INCLUDED” above |
This tour can be taken as a self-ride; contact us for details.
The above should be taken as a guide only as things can change. If you have any questions, please contact us.
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