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Route 66 Car Caravan Itinerary

Curious where we gon on our Rt66 caravans? Here's a rough idea of just a fraction of the great places you'll see on our trip. (itinerary always subject to change)


Day 1: Chicago

Begin your adventure in America’s third largest city, Chicago, as you meet your fellow travelers for a welcome dinner and trip briefing. This is a perfect opportunity to try Chicago’s famous deep-dish pizza!

Hotel: Palmer House Hilton (or similar)

Included meals: dinner

Featured stops: Beginning of Route 66 Sign, Cloud Gate


Day 4: STL to Springfield, MO

Start with a guided tour of Meramec Caverns, a Jesse James hideout, before continuing on to Cuba in Missouri where you’ll enjoy a stop at the iconic Wagon Wheel Motel for photos and shopping. From Cuba, we’ll head to Springfield with photo stops at Fanning’s Outpost, formerly the “World’s Largest Rocking Chair,” Munger Moss Motel, and the Lebanon Route 66 Museum before arriving in Springfield, MO, the birthplace of Route 66.

Hotel: Holiday Inn Express (or similar)

Included meals: breakfast, lunch

Featured stops: Meramec Caverns, Wagon Wheel Motel, Fanning Outpost, Lebanon RT66 Museum

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Day 7: OKC to Amarillo, TX

Your morning begins with a stop at the Stafford Air and Space Museum before heading to the Oklahoma Route 66 Museum. After, we'll head to Erick, Oklahoma for a quick stop at the town’s charming museum. From Erick, you’ll cross into Texas and spend some time exploring Shamrock and the iconic Tower Conoco Station and U-Drop Inn, as seen in the movie Cars.
After Shamrock, we’ll stop at the Devil’s Rope Barbed Wire Museum and World’s Largest Cross before arriving in Amarillo.


Dinner is on your own tonight, but we'll arrange for you to check out the Big Texan Steak Ranch!

Hotel: Cactus Cove (or similar)

Included meals: breakfast

Featured stops: Stafford Air & Space Museum, OK RT66 Museum, Tower Conoco, Devil's Rope Museum


Day 10: ABQ to Winslow, AZ

We’ll start at the El Rancho Motel, where all of the western stars stayed, then journey across the Painted Desert and cruise through the Petrified Forest National Park, the only park to have Route 66 pass through. We’ll make a quick stop in Holbrook at the Petrified Wood Store and a photo stop at the iconic Wigwam Motel before heading Jack Rabbit Trading Post then to Winslow where you’ll “Stand on the Corner” just like the Eagles song. Finish your day at the historic La Posada Hotel

Hotel: La Posada

Included meals: breakfast

Featured stops: El Rancho, Petrified Forest, Wigwam Motel, Winslow, Jack Rabbit Trading

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Day 13: Barstow to Los Angeles

Today it’s all about making it to the end of our Route 66 adventure in Santa Monica where you’ll get pictures with the End of the Trail Route 66 sign on the pier. We’ll make a quick stop at the California Route 66 Museum, too. After, celebrate the end of the trip with your new and old friends at our farewell dinner!

Hotel: Hyatt Regency LAX (or similar)

Included meals: breakfast, dinner

Featured stops: Elmer's Bottle Tree Ranch, CA RT66 Museum, Santa Monica Pier


Day 2: Chicago to Litchfield, IL

Start your morning with iconic Route 66 photo stops at filling stations in Dwight and O’Dell before arriving in Pontiac, Illinois, where you’ll explore the Route 66 Hall of Fame and the Pontiac Car Museum. Enjoy a quick stop in Atlanta, IL before heading down to Springfield for Lincoln’s Tomb, and then it’s off to Litchfield, IL for the night.

Holiday Inn Express (or similar)

Included meals: breakfast

Featured stops: Ambler Texaco Station, Pontiac Route 66 Museum, Lincoln's Tomb


Day 5: Springfield to OK City

Our first strop is at Gary’s Filling Station, a favorite for all Route 66 travelers. After, we take a quick jaunt to Galena, Kansas for some fun photo stops and cross into Oklahoma. We’ll make a quick stop at Mickey Mantel’s boyhood home then drive through Oklahoma's tribal lands with roadside attractions like the Blue Whale of Catoosa and POPs Soda Ranch.

Hotel: Courtyard Marriott (or similar)

Included meals: breakfast, lunch

Featured stops: Gary's Sinclair Station, Rainbow Bridge, Blue Whale, POPs Soda Ranch

Route 66 Slideshow-75.jpg

Day 8: Amarillo to Albuquerque

After spray painting your name on the Cadillacs at Cadillac Ranch, we’re heading to New Mexico with stops at the Midpoint Cafe in Adrian, Russell’s Travel Center, Tucumcari to visit the Blue Swallow Motel and TeePee Curios, and the Route 66 Auto Museum in Santa Rosa before arriving in Albuquerque. Enjoy dinner at the iconic 66 Diner in Albuquerque, New Mexico.

Hotel: TownePlace Suites Old Town (or similar)

Included meals: breakfast, dinner

Featured stops: Cadillac Ranch, Midpoint Cafe, Blue Swallow, Roadrunner, TeePee Curios, Route 66 Auto Museum

Desert View Watchtower Grand

Day 11: Grand Canyon!

Start your morning with a visit to the Cameron Trading Post where you’ll have the opportunity to buy authentic Native American gifts. After, we enter the Grand Canyon, one of the great wonders of the world. Spend the afternoon taking in the breathtaking sights before we drive to Williams, Arizona, a truly one-of-a-kind Route 66 town!

Hotel: La Quinta Inn (or similar)

Included meals: breakfast

Featured stops: Cameron Trading Post, the Grand Canyon, Williams AZ


Day 3: St. Louis Sightseeing

Enjoy a trip to the top of the Gateway Arch, a tour of one of America’s grandest cathedrals, the Cathedral Basilica, and a tour of the Budweiser brewery.

Hotel: Holiday Inn Downtown (or similar)

Included meals: breakfast

Featured stops: Gateway Arch, Cathedral Basilica, Budweiser Brewery

Oklahoma City Memorial-1.jpg

Day 6: OK City Sightseeing

Start the morning with a moving tour of
the Oklahoma City National Memorial and Museum before having the afternoon free to check out the National Cowboy Museum or the Botanical Gardens. Spend the rest of the afternoon relaxing in Oklahoma City’s hip Bricktown neighborhood.

Hotel: Courtyard Marriott (or similar)

Included meals: breakfast

Featured stops: Oklahoma City National Memorial


Day 9: Santa Fe Day Trip

Take a quick hop up the highway to Santa Fe in New Mexico, one of the most beautiful towns of the southwest. Enjoy a guided city tour and plenty of free time before returning
to Albuquerque.

Hotel: TownePlace Suites Old Town (or similar)

Included meals: breakfast

Featured stops: Guided tour of Santa Fe, NM, Madrid, NM

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Day 12: Williams to Barstow, CA

Spend the day going through some of the Route’s most memorable towns like Seligman, where the famed barber “Angel” has his shop. Angel was a major consultant for the movie Cars and is credited for saving Route 66 after the interstate came along. Next, it’s on to the funky trading post, Hackberry General Store, and Andy Devine’s very own Kingman before heading to the old mining town of Oatman with its wild burros roaming the town. We’ll make one last stop at Roy’s Motel and Café before landing in Barstow, California for the night.

Hotel: Ayres Hotel (or similar)

Included meals: breakfast

Featured stops: Seligman, AZ, Hackberry General Store, Kingman AZ, Cool Springs, Oatman, Roy's (Amboy)

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