Estimated read time: 5-6 minutes
Famously nicknamed the "Mother Road" by John Steinbeck in his classic novel The Grapes of Wrath, Route 66 spans roughly 2,400 miles from Chicago to Los Angeles.
No other route in America (and arguably the world) carries the same fame or cultural weight – almost everyone recognizes its name and iconic signs.
But few have meaningfully experienced it, and almost none have traveled it end to end to fully appreciate all the history, culture and sights it has to offer – which is exactly what you can do thanks to Southwest Adventure Tours.
Here's how you can experience Route 66 in all its glory over an immersive 12-day guided adventure.
The 12-day westbound Route 66 tour
Day 1: Chicago.
Kick off your Route 66 journey in the Windy City with classic deep-dish pizza (the locals will tell you the only pizza) and a walk to the official Begin Route 66 sign – plus a river cruise that lets you fully take in the city's famous skyline at sunset.
Key highlights:
- Chicago architecture river cruise.
- Route 66 Begin sign.
- Chicago-style deep-dish pizza.
Day 2: Chicago, Pontiac and Springfield, Ill.
Today is the day when you'll officially hit the "Mother Road", stopping at legendary diners, restored gas stations, and landmarks. The day ends in Springfield, Ill. with nostalgic Americana and the birthplace of the corn dog.
Key highlights:
- Lou Mitchell's diner (known as the "first stop on the Mother Road").
- Cozy Dog Drive-In (birthplace of the corn dog.)
Day 3: Springfield to St. Louis
Dive into more American history (a very common theme on this trip) with a stop at the Abraham Lincoln Presidential Library and Museum before crossing into Missouri along original Route 66 alignments.
A visit to Gateway Arch awaits when you get to St. Louis.
Key highlights:
- Abraham Lincoln Presidential Library and Museum.
- Old Chain of Rocks Bridge.
- Gateway Arch tram ride.
Day 4: St. Louis to Springfield, Mo.
As Route 66 winds through Missouri, travel across classic roadside attractions such as Missouri's "buried treasure." Enjoy plenty of quirky stops and oversized Americana as you make your way to Springfield for the second time on this trip (in a different state this time!)
Key highlights:
- Meramec Caverns.
- Cuban murals.
- Route 66's giant rocking chair.
Day 5: Springfield, Ill. to Tulsa, Okla.
Cross from Missouri into Kansas and Oklahoma, checking off more iconic Route 66 stops along the way. Stop by classic bridges, theaters, and whimsical landmarks before settling into Tulsa, Okla., a city deeply tied to Route 66 history.
Key highlights:
- Marsh Arch Bridge.
- Blue Whale of Catoosa.
- Cyrus Avery Plaza.
Day 6: Tulsa to Oklahoma City, Okla.
A full day of classic Route 66 storytelling, museums, and a sweet treat for good measure leads into Oklahoma City, Okla. where you'll end your day learning about the First American Nations – vital contributors to the cultural fabric of Route 66 (and modern America in general).
Key highlights:
- Route 66 Interpretive Center.
- First Americans Museum.
Day 7: Oklahoma City, Okla. to Amarillo, Tex.
Head west through the heart of Route 66 country as museums and small-town stops lead into the Texas Panhandle, where a bold Texas-sized dinner awaits.
Key highlights:
- Oklahoma City National Memorial.
- Oklahoma Route 66 Museum.
- Big Texan Steak Ranch.
Day 8: Amarillo to Albuquerque, Tex.
Leave Amarillo around the same time George Strait got there and embark on a journey that reveals the "Mother Road's" Southwest character, from the surreal Cadillac Ranch to the vibrant towns of Tucumcari and Santa Fe, NM.
Key highlights:
- Cadillac Ranch.
- Tucumcari Route 66 icons.
- Santa Fe historic plaza.
Day 9: Albuquerque, N.M. to Flagstaff, Ariz.
Travel west through cinematic desert landscapes, including the otherworldly scenery of Petrified Forest National Park and Winslow, a town made famous by the hugely successful and influential American rock band, the Eagles. End your day in eclectic and lively Flagstaff.
Key highlights:
- Petrified Forest National Park.
- Painted Desert.
- Winslow, Arizona.
Day 10: Flagstaff, Ariz. to San Bernardino, Calif.
As the tour nears its end, enjoy one of the most iconic Route 66 driving days that features more desert towns and the birthplace of the "Mother Road." End the day in San Bernardino, Calif. with a true classic: Overnight in the historic Wigwam Motel.
Key highlights:
- Seligman, the town responsible for keeping Route 66's historic status in the 1980s.
- Oatman Ghost Town.
- Wigwam Motel.
Day 11: Hollywood to Santa Monica, Calif.
The route so frequently featured in movies meets the place where these movies are made. Tour legendary sights and celebrity neighborhoods before reaching the official western terminus of Route 66. Your last day ends with ocean views and a farewell dinner on the pier – what else could you want?
Key highlights:
- Hollywood and Beverly Hills tour.
- Route 66 End Sign.
- Santa Monica Pier.
Day 12: Los Angeles to home
All good things come to an end, and day 12 is when you'll bid farewell to Route 66 and transfer to the airport.
Those who booked a later flight may want to savor a few extra hours at one of Southern California's beautiful beaches and reflect on an unforgettable journey.
Ready for your Route 66 adventure?
From expert-guided exploration to comfortable transportation in a Sprinter van to quality lodging, Southwest Adventure Tours takes care of the logistics so you can enjoy the experience.
Book your Route 66 adventure today and secure your spot for 2026!
