Your 12-day journey along Historic Route 66 begins at the world-famous Santa Monica Pier, the official western terminus of America’s Main Street. Standing at the edge of the Pacific Ocean, this iconic landmark marks the starting point of one of the most legendary roadways in the world and sets the tone for the adventure ahead.

Enjoy free time to explore the pier and surrounding area at your own pace. Stroll along the boardwalk, watch street performers, browse local shops, or simply take in sweeping ocean views as you soak up the excitement of the journey about to unfold. This is your chance to capture photos at the Route 66 “End of the Trail” sign and experience the historic significance of this beloved starting point.

In the evening, gather with your fellow travelers for a welcome dinner, a relaxed and celebratory way to begin your Route 66 experience. Share stories, meet your travel companions, and toast the road ahead. If you wish, linger after dinner to watch the sun set over the Pacific Ocean—a timeless and nostalgic moment that perfectly launches your eastbound journey along the Mother Road.

Lodging: Hampton Inn & Suites by Hilton Santa Monica

Meals: D

Start your day with a hearty breakfast, with the option to enjoy a peaceful morning walk along the beach before today’s adventure begins. The morning features a fun and informative sightseeing tour of Hollywood, West Hollywood, and Beverly Hills, offering an insider’s look at some of Los Angeles’ most famous neighborhoods.

Highlights include views of the Hollywood Sign, the Walk of Fame, Dolby Theatre, TCL Chinese Theatre, Capitol Records, the Sunset Strip, Rodeo Drive, the Laugh Factory, iconic filming locations, and glimpses of celebrity homes in Beverly Hills. You’ll also visit the original western end of Route 66, where America’s legendary highway once began its journey east.

Following the tour, enjoy free time for lunch on your own at a local Los Angeles restaurant. In the afternoon, travel east through San Bernardino and Victorville, officially transitioning onto historic Route 66 as you make your way toward the desert.

This evening, arrive in Barstow, California, a classic Route 66 town, where you’ll enjoy dinner at a local restaurant before settling in for an overnight stay—marking your first full night along the Mother Road.

Lodging: Holiday Inn & Suites Barstow

Meals: B, D

Today’s journey features a scenic drive across California’s Mojave Desert, where wide-open landscapes and historic roadways set the stage for a quintessential Route 66 experience. Enjoy stops in Needles, California, before crossing into Arizona and continuing to the legendary ghost town of Oatman.

Nestled at 2,700 feet along the original Route 66 between Needles and Kingman, Oatman is one of the Mother Road’s most memorable stops. Known for its quirky Old West charm, roaming burros, historic wooden storefronts, gift shops, and local eateries, this former mining town offers a lively step back in time.

From Oatman, sit back and enjoy a picturesque drive through desert mountain scenery as you travel to Kingman, Arizona. Here, stop for a group lunch at the iconic Mr. D’z Route 66 Diner, a beloved classic that captures the spirit of roadside Americana.

After lunch, experience the longest remaining continuous stretch of original Route 66, traveling through storied towns such as Peach Springs and Hackberry. Continue on to Seligman, proudly known as the Birthplace of Historic Route 66 and a must-visit destination for Route 66 enthusiasts. Learn how local barber Angel Delgadillo helped spark the preservation of Route 66 after the town was bypassed by Interstate 40, leading to the creation of the Historic Route 66 Association of Arizona.

Conclude the day in historic Williams, Arizona, where you’ll have time to stroll its charming main street, lined with classic Route 66 shops and landmarks. This evening, arrive in Flagstaff, a high-country mountain town rich in history and culture. Enjoy a free evening for dinner on your own, with time to explore Flagstaff’s lively downtown area.

Lodging: Little America Hotel (Flagstaff)

Meals: B, L

Begin the day with a scenic drive that dramatically transitions from Flagstaff’s high-altitude ponderosa pine forests to the rugged high-desert landscapes leading to historic Winslow, Arizona. This classic Route 66 town is rich in nostalgia and forever immortalized in song, offering a memorable stop along the Mother Road.

After time to explore Winslow, continue eastward to Petrified Forest National Park for included sightseeing and lunch. Travel through the vibrant Painted Desert, with its striking bands of color, and enjoy a drive along Blue Mesa, pausing for photo opportunities along the way. Inside the park, take a walk through the Rainbow Forest, where ancient petrified logs and fascinating geology tell the story of a landscape millions of years in the making.

Continue along historic Route 66 as you cross into New Mexico—known as the “Land of Enchantment.” In Gallup, stop at the iconic El Rancho Hotel, a beautifully preserved landmark celebrated for its 1930s elegance and Hollywood history, once hosting film stars and crews traveling through the Southwest.

Conclude today’s journey in Albuquerque, New Mexico, where the evening is free to explore the city’s historic Old Town at your own pace. Wander narrow streets lined with centuries-old adobe buildings, browse local shops featuring handcrafted jewelry, rugs, and pottery, and savor traditional New Mexican cuisine, including enchiladas and warm sopaipilla pastries. The Old Town Plaza provides a charming backdrop, watched over by the 18th-century San Felipe de Neri Church—a fitting end to another unforgettable day on Route 66.

Lodging: Hilton Garden Inn ABQ Uptown

Meals: B, L

Begin your day traveling north along the original Route 66 to Santa Fe, New Mexico, one of the oldest and most culturally rich cities in the United States. Enjoy time to explore this historic destination, including a visit to La Fonda on the Plaza, a legendary hotel that has welcomed Route 66 travelers for generations.

Continue east to Santa Rosa for lunch before traveling on to Tucumcari, a town synonymous with Route 66 nostalgia. Here, you’ll see some of the Mother Road’s most iconic landmarks, including the Blue Swallow Motel, Tee Pee Curios, La Cita Mexican Restaurant, and a glowing tribute monument celebrating the legacy of Route 66.

After your time in Tucumcari, cross into Texas and arrive at the geographic Route 66 Midpoint in Adrian, a classic photo stop marking the halfway point between Chicago and Santa Monica. From there, continue to Amarillo for one of the most recognizable Route 66 attractions—Cadillac Ranch. Created by a group of San Francisco–based artists, this unforgettable roadside art installation features ten vintage Cadillacs buried nose-down in the Texas Panhandle, their colorful tail fins pointed skyward.

This evening, arrive in Amarillo, Texas, check into your hotel, and cap off the day with a true Texas tradition at the legendary Big Texan Steak Ranch, famous for its bold flavors and larger-than-life atmosphere.

Lodging: Drury Inn & Suites

Meals: B, D

Enjoy a few additional Route 66 highlights in Amarillo this morning before continuing your journey east into Oklahoma. Your first stop is the small town of Erick, where quirky roadside attractions and offbeat displays perfectly capture the spirit of rural Route 66 and classic Americana.

Next, travel to Clinton, Oklahoma, for a visit to the acclaimed Oklahoma Route 66 Museum. Often considered one of the finest Route 66 museums along the entire route, this immersive experience tells the story of the Mother Road through the lens of the state where Route 66 was born. Discover iconic imagery, personal stories, and enduring myths while learning about the dreams, challenges, and craftsmanship that shaped this legendary highway. Enjoy free time for lunch on your own in this eclectic Route 66 town.

Continue east to Oklahoma City, where you’ll visit the First Americans Museum, a world-class cultural institution opened in 2021. Through powerful exhibits and storytelling, the museum highlights the histories, cultures, and contemporary contributions of the 39 First American Nations present in Oklahoma—an essential and meaningful chapter in the broader Route 66 narrative.

After the visit, transfer to your hotel in the vibrant Bricktown District. The evening is free to explore the area at your own pace, with numerous options for dining, waterfront walks, and entertainment in one of Oklahoma City’s most lively neighborhoods.

Lodging: Hampton Inn & Suites Oklahoma City-Bricktown, OK

Meals: B, L
 

After breakfast, begin the day with a meaningful stop at the Oklahoma City National Memorial, honoring the victims, survivors, rescuers, and all those impacted by the tragic bombing of April 19, 1995. This reflective visit offers an important moment of remembrance before continuing today’s Route 66 journey.

Travel north toward Tulsa, Oklahoma, with several memorable stops along historic Route 66. Your first stop is POPS, one of the most iconic attractions along old Highway 66. With more than 600 varieties of soda, a POPS soda expert can help you discover a new favorite or revisit a classic, making for a fun and refreshing break.

Next, visit the Arcadia Round Barn, a beautifully restored architectural landmark and one of the most photographed sites on Route 66 in Oklahoma. Continue on to Chandler for a visit to the Route 66 Interpretive Center, which takes visitors on a visually engaging “drive” through Oklahoma’s Route 66 history from the 1920s to the present day—what John Steinbeck famously referred to as the “Mother Road” in The Grapes of Wrath. While in Chandler, also stop at McJerry’s Route 66 Gallery, home to Jerry McClanahan, an award-winning artist, Route 66 historian, and writer.

A brief stop will be made in Davenport before arriving in Sapulpa for a visit to Gasoline Alley Classics and the historic Rock Café, both celebrating the golden age of Route 66. From there, continue on to Tulsa, where you’ll visit the Route 66 Historical Village and Cyrus Avery Centennial Plaza, honoring Cyrus Avery, widely known as the Father of Route 66.

Conclude the day with time to explore Tulsa and additional Route 66 landmarks before settling in for a relaxing evening at your hotel.

Lodging: Embassy Suites Tulsa, Ok       

Meals: B, L

After breakfast, depart Tulsa and continue your journey along historic Route 66, beginning with a stop in Miami, Oklahoma, for a guided tour of the beautifully restored Coleman Theatre—a stunning example of early 20th-century Route 66 architecture.

Traveling along the Mother Road, enjoy additional iconic stops at Ed Galloway’s Totem Pole Park and the whimsical Blue Whale, both beloved landmarks that capture the playful spirit and roadside charm of Route 66.

As you enter Kansas, pause for photos at Cars on the Route in Galena, followed by a visit to the famous Marsh Arch Bridge, one of the most treasured and photogenic remnants of Route 66 history.

After lunch, continue east toward Springfield, Missouri, passing through classic Route 66 towns such as Spencer, Avilla, Carthage, and Joplin, with additional stops at historic sites including the Gary Gay Parita as time allows. The afternoon is filled with nostalgic exploration and memorable photo opportunities that showcase the enduring legacy of America’s Main Street.

Arrive in Springfield in the early evening, where you’ll enjoy dinner at the renowned Jimm’s Steakhouse before checking in to your overnight accommodations and settling in for the night.

Lodging: Hampton Inn & Suites Springfield
        
Meals: B, D

This morning features a variety of memorable stops along the Route 66 corridor, beginning in Rolla, Missouri, home to several iconic roadside attractions. Visit the world-famous Route 66 Giant Rocking Chair, the Giant Faucet, and Route 66 Motors, each offering classic photo opportunities and a dose of nostalgic Americana.

Continue on to Cuba, Missouri, where you’ll have time to explore the town’s 14 vibrant Route 66 murals. Known as “Route 66 Mural City,” Cuba offers a charming look at the history and spirit of the Mother Road, with time to wander at your own pace and enjoy lunch on your own.

After lunch, travel east along the Old Road to one of Route 66’s most iconic natural attractions—Meramec Caverns. Hidden beneath the rolling hills of the Meramec Valley, this expansive cavern system is renowned for its colorful mineral formations and fascinating geological features. Enjoy a guided tour that reveals the history, legends, and natural beauty of these remarkable underground chambers.

Following your visit, continue to St. Louis, Missouri. In the late afternoon, experience the city’s signature landmark with a visit to the Gateway Arch, including a tram ride to the top for sweeping views of the Mississippi River and downtown skyline. The evening is free to explore downtown St. Louis, including Union Station, Busch Stadium, and the scenic Mississippi River waterfront.

Lodging: Drury Plaza Hotel St. Louis At The Arch

Meals: B

Begin your day with a memorable photo opportunity at the historic Chain of Rocks Bridge, featuring a striking view of the Gateway Arch rising in the distance across the Mississippi River. This iconic Route 66 bridge offers a powerful visual link between the Mother Road and America’s heartland.

Continue traveling along historic Route 66, making stops in charming Illinois towns including Granite City, Mt. Olive, Litchfield, Girard, Virden, and Auburn, each offering a glimpse into small-town Americana and Route 66 heritage.

In the afternoon, arrive in Springfield, Illinois, for a visit to the Abraham Lincoln Presidential Library & Museum, one of the nation’s premier presidential museums. Through engaging exhibits, the museum chronicles the life of the 16th President of the United States and the events surrounding the American Civil War. You’ll also see Abraham Lincoln’s home, providing deeper insight into his personal and political life.

After checking into your hotel, gather with the group for a fun and nostalgic dinner at the Cozy Dog Drive-In, officially recognized as the birthplace of the corn dog—a beloved Route 66 classic and the perfect way to end the day.

Lodging: Drury Inn & Suites Springfield, IL
 
Meals:  B,L, D

After a brief driving tour of Route 66 landmarks in Springfield, continue north with additional stops in Lincoln, Normal, and Towanda, tracing the final stretches of the Mother Road through central Illinois. Pause in Pontiac for a visit to the Route 66 Association of Illinois, where exhibits and memorabilia celebrate the preservation and legacy of America’s Main Street. Enjoy lunch on your own in this welcoming Route 66 community.

Next, begin the final leg of your journey to Chicago, with classic roadside stops along the way, including the historic Standard Oil Station in Odell and Ambler’s Texaco Station in Dwight—two beautifully preserved symbols of Route 66’s golden era.

Upon entering Chicago, enjoy a drive-by view of the iconic Willis Tower before arriving at the official start and finish points of Route 66, where you’ll have time for photos and reflection at the end of this legendary cross-country route.

In the evening, celebrate the completion of your journey with an iconic Chicago-style deep-dish pizza dinner at a local favorite such as Giordano’s or The Exchequer. Cap off the night with a spectacular evening Architecture River Cruise, as Chicago’s world-renowned skyline glows at dusk—providing a serene and unforgettable finale to your Route 66 adventure.

Lodging: Radisson Blu Aqua Hotel, Chicago, IL

Meals B, D

Today marks the conclusion of your unforgettable journey along historic Route 66. Depart the Windy City of Chicago with lasting memories of America’s Main Street, the places you’ve explored, and the stories that brought the Mother Road to life.

Transfers to Chicago Midway or Chicago O’Hare International Airport will be provided as needed, based on flight schedules and traffic conditions. We wish you safe travels and hope the spirit of Route 66 stays with you long after the journey ends.

Meals: B