“Get your kicks on Route 66” is a beloved song everyone knows —and for the Mother Road’s 100th anniversary in 2026, it’s still the best advice around. No highway in America is more iconic than Route 66, the storied ribbon of asphalt immortalized in songs, stories, and the American imagination. To honor this centennial milestone, we’ve crafted a special tribute journey packed with everything you’ve come to expect from us: small-group touring, superb hotels, two-night stays in both Santa Fe and the Grand Canyon, scenic train travel, legendary dining, and—naturally—the iconic Route 66; the great American road trip.

Your adventure begins in downtown Chicago and winds westward through some of Route 66’s most famous waypoints—St. Louis, Springfield, Oklahoma City, Amarillo, Santa Fe, Winslow, and Kingman, just to name a few. Along the way, the road reveals its full grandeur: the Painted Desert and Petrified Forest, the majestic Grand Canyon, and the Pacific Coast Highway at Santa Monica, where Route 66 meets the Pacific. You’ll also encounter marvels of human achievement, such as St. Louis’s soaring Gateway Arch and the historic Grand Canyon Railway.

This journey is a true passage through time and across America’s legendary highway. Quirky roadside treasures await at every turn—the Chain of Rocks Bridge in St. Louis, the shimmering Meramec Caverns, the beloved Blue Whale of Catoosa, the Cadillac Ranch in Amarillo, and Meteor Crater near Winslow. Speaking of Winslow, you’ll enjoy an unforgettable overnight stay at the beautifully restored La Posada Hotel, the last great hotel built by the Santa Fe Railway. And of course, there’s time to stand on that corner in Winslow, made famous by the Eagles.

Great dining is woven throughout your trip. Savor deep-dish pizza at Giordano’s in Chicago, indulge in Ted Drewes Frozen Custard in St. Louis, and sample one of America’s most celebrated hamburgers in El Reno, Oklahoma. A highlight awaits in Amarillo: a magnificent steak dinner at the legendary Big Texan Steak Ranch.

After crossing the country in comfort and wonder, your adventure concludes at Santa Monica’s iconic “End of the Trail” sign—the triumphant finale to your Route 66 odyssey. This centennial year is the perfect moment to embrace the open road, the wide sky, and the trip of a lifetime on America’s most legendary highway.

Your adventure begins where the Mother Road itself begins. Check into the elegant Silversmith Hotel, set within Chicago’s vibrant Loop and just steps from Grant Park—where Route 66 officially launches its legendary westward run. This evening, enjoy a casual welcome dinner at Giordano’s, famed for its classic Chicago deep-dish pizza, and get acquainted with your fellow travelers. A perfect and delicious start to a nostalgic American journey.

Fuel up with an unforgettable breakfast at Lou Mitchell’s—an institution as iconic as Route 66 itself. Then sit back and relax aboard a scenic rail journey from Chicago to St. Louis, tracing the historic path once traveled by the Union Pacific. Arrive this afternoon and visit the Gateway Arch, America’s shimmering tribute to westward ambition and adventure. Your charming hotel lies just steps from the Arch, offering an effortless transition into a leisurely evening at your own pace.

Start your morning with a guided sightseeing tour featuring graceful Forest Park and the stunning Basilica of St. Louis. Continue to the legendary Meramec Caverns—one of Route 66’s most celebrated roadside attractions. Then enjoy a scenic drive through classic Ozark landscapes en route to Springfield, the city where the name “Route 66” was first coined. Settle in for a restful overnight stay, with the evening at leisure to relax or explore at your own pace.

Today serves up a medley of Mother Road delights: explore the lively Mother Road Market in Tulsa, snap a photo at the delightfully quirky Blue Whale of Catoosa, and admire the mid-century charm of the Will Rogers Theatre. Continue to POPS 66, a modern Route 66 icon crowned by its towering, neon-bright soda bottle. This evening, settle into the historic Skirvin Hilton—Oklahoma City’s storied grand dame and a perfect retreat after a full day of adventure.

This morning, pass the whimsical Milk Bottle Grocery—yes, an actual building shaped like a milk bottle—before visiting Lucille’s Historic Highway Gas Station, a beloved Route 66 landmark. Enjoy a classic lunch in El Reno at an old-school diner renowned for serving some of the best hamburgers on the Mother Road. Crossing into Texas, stop at the beautifully preserved U-Drop Inn in Shamrock, an Art Deco treasure that even inspired scenes in Pixar’s Cars. Continue to Amarillo for a visit to the surreal Cadillac Ranch, where ten Cadillacs stand nose-down in the Texas earth, creating an ever-changing spray-painted art installation. This evening, enjoy dinner at the legendary Big Texan Steakhouse—an authentic taste of Texas hospitality.

Follow Route 66 beneath wide-open Southwestern skies to Tucumcari, where you’ll take in classics like the iconic Blue Swallow Motel and the delightfully quirky Tee Pee Curios. Continue to the Blue Hole of Santa Rosa, a sparkling spring-fed pool famed for its crystal-clear waters, before tracing the historic Santa Fe Loop—an early and scenic alignment of Route 66. Arrive in timeless Santa Fe and enjoy a stroll past landmarks such as La Fonda on the Plaza and the venerable Palace of the Governors. This evening features a delicious New Mexico dinner as you settle in for a relaxing two-night stay.

Today’s journey is a feast of natural beauty. Trace preserved stretches of Route 66 to the Painted Desert and the Petrified Forest—otherworldly landscapes that spark the imagination with their vibrant colors and ancient stonewood. Continue to Holbrook for a look at the famed Wigwam Motel before rolling into Winslow, where “standing on the corner” is practically a rite of passage for any Route 66 traveler. Tonight, settle into La Posada, the last-built and beautifully restored Harvey House hotel—an architectural masterpiece and an unforgettable step back in time.

This morning, visit Meteor Crater, a massive and awe-inspiring impact site formed 50,000 years ago. Take in sweeping panoramic views and explore the excellent on-site museum—an unforgettable stop for any traveler. Continue to Williams, a quintessential Route 66 town brimming with neon lights, Western charm, and classic storefronts. Enjoy a relaxing evening as you begin your two-night stay in this iconic locale.

All aboard the historic Grand Canyon Railway! Step back in time and travel the same route early visitors took in 1901. At the South Rim, embark on a full-day adventure exploring the Grand Canyon’s most breathtaking sights: Desert View, Ooh Aah Point, Grandview, and the charming Grand Canyon Village. In the late afternoon, return to Williams and unwind while soaking in the town’s vibrant neon-lit streets and classic Route 66 charm.

Today you’ll journey along one of the most nostalgic stretches of Route 66. Cruise the original road through Seligman, Peach Springs, and Hackberry, where classic Burma Shave signs and timeless Americana peek out against the rugged Black Mountains. Arrive in Laughlin, a serene desert oasis on the Colorado River, and unwind with a relaxing evening surrounded by the desert’s quiet beauty.

Cross the vast Mojave Desert, pausing at Roy’s Motel & Café in Amboy, one of Route 66’s most photographed landmarks, and the quirky Bottle Tree Ranch, a true roadside wonder. As the Pacific Ocean comes into view, follow the final miles of the Mother Road to the iconic Santa Monica Pier, the emotional “end of the trail.” Tonight, cap off your adventure with a memorable farewell dinner to celebrate the journey.

Depart with your heart full and your camera ready, carrying memories of vintage motels, sweeping deserts, glowing neon nights, historic cafés, and the timeless spirit of America’s most legendary road—all woven into thirteen unforgettable days.