Route 66 Road Trip Tour
April 22 - May 5, 2027
TRIP HIGHLIGHTS
Route 66 from Chicago to Los Angeles
Chicago Architectural Cruise
St Louis Gateway Arch
Historic Museums
Charming Towns
Grand Canyon National Park
Petrified Forest National Park
Santa Fe, New Mexico
INCLUDED IN TOUR
Professional tour director
Professional motor coach driver
All flights (regional airport departures may cost more)
Top quality accommodations
Luxury motor coaches
Many meals on tour, equal amount of breakfasts and lunches/dinners
Tips on all meals
All taxes, fees, visas, etc. included in total price of tour
Personalized service
Final documents for trip details, 8 weeks prior to departure
Luggage handling
Much, much more!
NOT INCLUDED IN TOUR
Every meal not included – guests are informed about how much more money to expect to pay for meals prior to departure
Tips for tour director and driver
($8 - $12 per person per day is recommended)Baggage Fees when flying
Personal expenses (souvenirs, other personal costs, etc.)
For generations, Route 66 has symbolized freedom, adventure, and the spirit of the open road. Stretching from the shores of Lake Michigan to the Pacific Ocean, this legendary highway winds through the heart of America, connecting vibrant cities, charming small towns, desert landscapes, and unforgettable roadside attractions. On this incredible coast-to-coast journey, experience the nostalgia of classic Americana while discovering the history, culture, and natural beauty that made Route 66 one of the most famous roads in the world.
From the towering skyline of Chicago to the iconic Santa Monica Pier in Santa Monica, each day brings new scenery and memorable experiences. Travel through eight fascinating states as you explore vintage diners, neon-lit motels, historic landmarks, Native American culture, cowboy country, and the dramatic landscapes of the American Southwest.
ITINERARY
Day 1: Fly Into Chicago
*Dinner Included
Your adventure begins as you arrive in the Windy City — the historic starting point of the Mother Road. Join your fellow travelers for a welcome dinner and meet your Tour Director.
Chicago, IL
Day 2: Chicago Architectural Tour
*Breakfast Included
Today we explore the rich history and stunning architecture of Chicago. Enjoy a guided architectural cruise along the Chicago River as towering skyscrapers and historic landmarks tell the story of this remarkable city. The remainder of the day is free to explore the Magnificent Mile, Millennium Park, Navy Pier, or sample Chicago’s famous deep-dish pizza.
Chicago, IL
Day 3: Get your kicks in Pontiac, Illinois
*Breakfast Included
Today we officially hit the Mother Road! As we travel through the Illinois countryside, Route 66 begins to come alive with vintage signs, restored gas stations, and classic roadside attractions. We arrive in Pontiac, a beloved Route 66 town known for its colorful murals, museums, and small-town charm. Continue to Springfield, the former home and final resting place of President Abraham Lincoln!
Springfield, IL
Day 4: It goes through St Louis, MO
*Breakfast Included
Start the day by visiting the Abraham Lincoln Presidential Library. Continue westward to St. Louis, where Route 66 history meets the mighty Mississippi River. Known as the “Gateway to the West,” St. Louis offers a fascinating blend of history, culture, and iconic American landmarks. We take a ride to the top of the famous Gateway Arch for views over the West.
St Louis, MO
Day 5: Down through Joplin, MO
*Breakfast & Lunch Included
Today we journey through the scenic Ozarks toward Joplin. Along the way, enjoy classic Americana scenery, nostalgic roadside stops, and reminders of the golden age of American road travel. (B, L)
Joplin, MO
Day 6: Oklahoma City - Oh So Pretty
*Breakfast Included
Briefly cut into Kansas to see the town that helped inspire the blockbuster animated movie “Cars.” Continue into Tulsa to see Buck Atom’s Cosmic Curios and stop in for lunch at the Mother Road Market. Cross into Oklahoma where Route 66 culture thrives. Arriving in Oklahoma City, we discover a city rich in western heritage, cowboy culture, and revitalized entertainment districts that perfectly blend old and new.
Oklahoma City, OK
Day 7: You’ll See Amarillo
*Breakfast & Dinner Included
Visit the Oklahoma City National Memorial & Museum. Continue to the National Route 66 Museum and Transportation Museum. Travel across the wide-open landscapes of the Texas Panhandle to legendary Amarillo. Famous for its cowboy culture, colorful roadside attractions, and Route 66 history, Amarillo captures the rugged spirit of the American West. Tonight, enjoy an included dinner at The Big Texan Steak Ranch & Brewery.
Amarillo, TX
Day 8: Santa Fe, NM
*Breakfast & Lunch Included
Before leaving Texas, see the quirky public art installation featuring half-buried vintage Cadillacs at Cadillac Ranch. Today we pass the halfway point of Route 66 and travel to the historic town of Tucumcari, famous for vintage Neon signs, retro motels, and vibrant public murals! Today we enter the enchanting Southwest and arrive in Santa Fe — one of America’s oldest and most culturally rich cities. Admire the adobe architecture, browse local art galleries, and experience the unique blend of Native American, Spanish, and Southwestern traditions.
Santa Fe, NM
Day 9: Albuquerque, NM
*Breakfast Included
Continue to Albuquerque where neon Route 66 signs, Southwestern cuisine, and dramatic desert landscapes create an unforgettable atmosphere. Explore the historic Old Town district, browse local shops, and discover the unique blend of Native American, Hispanic, and Western cultures that define New Mexico.
Albuquerque, NM
Day 10: Gallup, NM & Flagstaff, AZ
*Breakfast & Dinner Included
Travel deeper into the Southwest to Gallup, a historic railroad town known for its Native American culture, trading posts, and dramatic desert scenery. Visit viewpoints within Petrified Forest National Park and drive by the famous Wigwam Motel before settling into Flagstaff, AZ for the night!
Flagstaff, AZ
Day 11: Grand Canyon and Williams, AZ
*Breakfast & Lunch Included
Take a short side trip from Route 66 to visit the iconic Grand Canyon, one of the Seven Natural Wonders of the World. Marvel at the breathtaking vistas before returning to historic Route 66. Continue to Williams, one of the best-preserved Route 66 towns in America. Historic storefronts, western charm, and classic diners transport visitors back to the golden age of road travel.
Williams, AZ
Day 12: Kingman & Barstow
*Breakfast Included
Travel through some of the most authentic remaining stretches of Historic Route 66. Stop in Seligman, often considered the birthplace of the Route 66 preservation movement, where vintage signs, classic cars, and nostalgic storefronts capture the spirit of the Mother Road. Continue through Kingman and across the vast Mojave Desert before arriving in Barstow, a historic railroad town that has welcomed travelers for generations.
Barstow, CA
Day 13: Santa Monica
*Breakfast & Dinner Included
Today we travel through Southern California, following the final miles of the legendary Mother Road. Along the way, enjoy classic Route 66 landmarks, vintage diners, and roadside attractions that evoke the golden age of American road travel. This afternoon we arrive at the iconic Santa Monica Pier, where Route 66 meets the Pacific Ocean. Celebrate the completion of your cross-country adventure with a farewell dinner overlooking the California coast.
Santa Monica, CA
Day 14: Depart for Home
After an unforgettable journey across America, we depart for home filled with incredible memories, new friendships, and stories from one of the world’s most legendary highways.
