An American Journey: Route 66

Your adventure begins where the Mother Road itself begins. Settle in at the Silversmith Hotel, nestled in Chicago’s vibrant Loop and just steps from Grant Park—where Route 66 officially starts its westward run.

Begin with breakfast at Lou Mitchell’s, then travel by train from Chicago to St. Louis.

Start your morning with a sightseeing tour featuring graceful Forest Park and the Basilica of St. Louis.

Today brings a medley of Mother Road delights: the bustling Mother Road Market in Tulsa, the quirky Blue Whale of Catoosa, the mid-century Will Rogers Theatre, and the modern neon-inspired icon POPS 66 with its colossal soda bottle. You’ll overnight at the historic Skirvin Hilton, Oklahoma City’s grand dame and the perfect place to rest after a day of adventure.

This morning we pass the Milk Bottle Grocery—yes, a building shaped like a milk bottle—and visit Lucille’s Historic Highway Gas Station. Lunch in El Reno is a treat, at an old-school diner for some of the best Route 66 hamburgers anywhere.

Follow Route 66 through wide-open skies to Tucumcari, where you’ll see the Blue Swallow Motel and quirky Tee Pee Curios. Pause at the Blue Hole of Santa Rosa, a sparkling natural pool, before taking the historic Santa Fe Loop—an early alignment of Route 66.

This morning’s city tour includes the Loretto Chapel and its “Miraculous Staircase. ” The rest of the day is yours—wander the art galleries, museums, and boutique shops that make Santa Fe one of America’s most towns. Dinner tonight is on your own, with dozens of wonderful restaurants to choose from.

Today’s journey is a feast of natural beauty. Travel along preserved stretches of Route 66 to the Painted Desert and the Petrified Forest—otherworldly landscapes that stir the imagination.

Visit Meteor Crater, with its viewpoints and museum.

Grand Canyon Railway! Ride this historic line just as early travelers did in 1901.

Today is one of the most nostalgic stretches of Route 66 anywhere. Travel the original road through Seligman, Peach Springs, and Hackberry—classic stops dotted with Burma Shave signs and vintage Americana, framed by the rugged Black Mountains.

Cross the Mojave Desert, stopping at Roy’s Motel & Café in Amboy—one of the most photographed landmarks on Route 66—and the whimsical Bottle Tree Ranch. As the Pacific draws near, follow the final miles of the Mother Road to the Santa Monica Pier, the emotional “end of the trail. ” Celebrate your journey tonight with a memorable farewell dinner.

The journey ends today.