Hit the Road and explore the iconic Route 66 like never before! Unravel the best Route 66 itineraries, scenic drives, and captivating landmarks with our ultimate guide.
Route 66, the granddaddy of all American roads, is calling your name! It’s time to ditch the mundane and dive headfirst into a world of quirky roadside attractions, breathtaking vistas, and enough stories to fill a lifetime of dinner parties.
When it comes to Route 66, this ain’t your average joyride. It’s a historic pilgrimage that will have you feeling like a time traveler, cruising through the golden era of Americana while jamming to tunes that make you want to disco in your car seat.
So, make sure you have those fanny packs ready and adjust your sunglasses because this ride will transport you to a different world.
This route features the Windy City, sunny beaches of California, and more! We’ll take you on a rollercoaster ride filled with laughter, adventure, and perhaps a few pit stops for an emergency karaoke session. Let’s begin:
Itinerary 1: Classic Route 66 Cruising
Day 1: Chicago, Illinois – The Windy City Welcome
Welcome to the starting point of your epic journey! Begin your Route 66 adventure in Chicago, and don’t forget to grab a deep-dish pizza before you hit the road. Visit the Museum of Science and Industry of Chicago known for being the largest science center in the Western Hemisphere.
Afterward, take a selfie with the famous “Route 66 Begin” sign before heading west.
Day 2: St. Louis, Missouri – Gateway Arch and Beyond
Today’s destination is St. Louis, home to the magnificent Gateway Arch. Take the tram ride to the top and enjoy breathtaking views of the city and the Mississippi River. Later, head to the City Museum, a wacky wonderland of slides, tunnels, and eclectic exhibits.
Day 3: Tulsa, Oklahoma – Neon Lights and Art Deco Delights
As you cross into Oklahoma, you’ll find yourself in Tulsa, a city filled with fascinating history and art. Explore the Gilcrease Museum, boasting an extensive collection of Native American art. At night, immerse yourself in the neon lights of the iconic Route 66, reminiscent of a bygone era.
Day 4: Amarillo, Texas – Cadillac Ranch and the Big Texan
Welcome to the Lone Star State! Amarillo awaits with the legendary Cadillac Ranch, a quirky art installation featuring half-buried cars. Afterward, visit the Big Texan Steak Ranch and attempt their 72 oz steak challenge – if you dare!
Day 5: Santa Fe, New Mexico – Southwestern Delights
Get ready for a taste of the Southwest! Santa Fe beckons with its adobe-style architecture and vibrant art scene. Meander through the historic Plaza, and don’t miss the Georgia O’Keeffe Museum, celebrating the work of this renowned artist.
Itinerary 2: Nature’s Wonderland
Day 6: Albuquerque, New Mexico – Balloons and Beyond
Today, head to Albuquerque and prepare for a sky-high adventure! If you’re lucky, catch the annual Albuquerque International Balloon Fiesta, where the sky is painted with colorful hot air balloons. For a unique experience, take a hot air balloon ride yourself and witness the stunning landscape from above.
Day 7: Petrified Forest National Park, Arizona – A Prehistoric Adventure
Leave the bustling city behind and immerse yourself in the otherworldly landscapes of Petrified Forest National Park. Explore the ancient petrified trees that date back millions of years and discover the fascinating archeological sites.
Day 8: Grand Canyon, Arizona – Nature’s Masterpiece
No Route 66 itinerary would be complete without a visit to the Grand Canyon! Be prepared to be awestruck by the sheer size and beauty of this natural wonder. Hike along the rim, take a mule ride, or opt for a scenic helicopter tour for a breathtaking perspective.
Day 9: Las Vegas, Nevada – Bright Lights and Big Wins
It’s time to add a little glitz and glamor to your adventure. Arrive in Las Vegas, where you can try your luck at the casinos, watch world-class shows, and indulge in gourmet dining. Remember, what happens in Vegas stays in Vegas!
Itinerary 3: Wild West And Roadside Wonders
Day 10: Flagstaff, Arizona – Ponderosa Pines and Cosmic Crater
Head to Flagstaff, a charming mountain town surrounded by Ponderosa pines. Visit the Lowell Observatory for stargazing and explore the Meteor Crater, a reminder of cosmic encounters from eons past.
Day 11: Holbrook, Arizona – Into the Painted Desert
As you journey through the Painted Desert, stop in Holbrook to see the iconic Wigwam Motel. Spend the night in a teepee for a quintessential Route 66 experience!
Day 12: Winslow, Arizona – Standing on the Corner
Take it easy in Winslow, Arizona, and stand on the corner made famous by the Eagles’ song. Relive the classic rock era as you stroll through this charming town.
Day 13: Flagstaff to Los Angeles, California – From Mountains to Ocean
Today, you’ll complete your Route 66 journey as you approach the final destination – Los Angeles. Enjoy the scenic drive through the San Gabriel Mountains before reaching the bustling city of LA.
Itinerary 4: Endless Summer – Route 66 Beach Edition
Day 14: Los Angeles, California – Beach Vibes Begin
Start your beach adventure in Los Angeles by visiting Venice Beach and enjoying the lively boardwalk scene. Don’t forget to snap a picture of the iconic “California” lifeguard tower!
Day 15: Santa Monica, California – Pier Fun and Ocean Breeze
Head over to Santa Monica and experience the Santa Monica Pier with its vintage carousel and Pacific Park amusement rides. Take a leisurely bike ride along the beach bike path and savor the ocean breeze.
Day 16: Malibu, California – Surfers’ Paradise
Drive up the picturesque Pacific Coast Highway to Malibu, known for its stunning beaches and celebrity sightings. Grab your board and hit the waves, or simply relax on the sandy shores.
Day 17: Santa Barbara, California – Spanish Style and Wine Delights
Travel to Santa Barbara, where you’ll find Spanish-style architecture and a vibrant wine scene. Take a stroll through the Santa Barbara Mission and treat yourself to some exquisite local wines.
Day 18: San Luis Obispo, California – Beaches and Bubblegum Alley
Explore the charming town of San Luis Obispo, home to Bubblegum Alley – a quirky alleyway adorned with chewed gum from visitors over the years. Visit nearby Avila Beach for some fun in the sun.
Day 19: San Francisco, California – Golden Gate and Beyond
Your final stop on this beach-themed itinerary is San Francisco. Experience the iconic Golden Gate Bridge and indulge in delicious seafood at Fisherman’s Wharf. Take a cruise to Alcatraz Island for a glimpse into its intriguing history.
Final Words
Congratulations, road warrior! You’ve just completed one of the most epic adventures of your life – a Route 66 trip to remember forever. The bustling cities, the tranquil beaches, you’ve experienced the heart and soul of America, one mile at a time.
But remember, the journey doesn’t end here. Route 66 is not just a road; it’s a symbol of freedom and exploration. So, keep that adventurous spirit alive, and who knows where the next road will take you?
Until then, keep on cruisin’ and embracing the open road. Happy travels!