On the Road Again: Route 66 Expedition

Road Trip Chronicles – Exploring Route 66 from Chicago to Santa Monica

This past week on social channels, we’ve been sharing pictures from our adventure down Route 66, and now we’re excited to share the itinerary we followed. From the bustling streets of Chicago to the sun-kissed shores of Santa Monica, join us on this unforgettable adventure along the Mother Road where you will immerse yourself in its rich history and vibrant culture.

Beginning of Route 66 Sign, Downtown Chicago

Day One – Chicago, IL

  • Lodging: Virgin Hotels Chicago
  • Attractions of Note: Our journey begins amidst the bustling streets of Chicago. Take a stroll through Millennium Park and marvel at the iconic Bean sculpture. Immerse yourself in history at The Field Museum, home to an impressive collection of artifacts and exhibits. Enjoy a Chicago Architecture River Cruise along the Chicago River to learn about the unique history of the city. Cap off the day with a visit to Navy Pier for some classic waterfront entertainment.
The Gateway Arch, St. Louis

Day Two

The Blue Whale of Catoosa, Oklahoma

Day Three

  • Start: Saint Louis, MO
  • Stop: Tulsa, OK
  • Miles/Hours on Road: 394 miles, 5 hours, 48 minutes
  • Lodging: Tulsa Club Hotel, Curio Collection by Hilton
  • Attractions of Note: In Fanning, Missouri, see the former world’s biggest rocking chair, before heading Galena, Kansas where a homage is made to the Pixar animated feature, Cars, which was inspired by Route 66. In Oklahoma, he sure to check out to the Route 66 Interpretative Center in Chandler and the National Museum of Cowboy and Western Heritage in Oklahoma City. Don’t miss the chance to snap a photo with the iconic Blue Whale of Catoosa in Catoosa, Oklahoma! Arriving In Tulsa, for the evening be sure to take in the vibrant culture of Tulsa’s Arts District, filled with galleries, boutiques, and cafes.
Cadillac Ranch, Amarillo

Day Four

  • Start: Tulsa, OK
  • Stop: Amarillo, TX
  • Miles/Hours on Road: 365 miles, 5 hours, 17 minutes
  • Lodging: Holiday Inn Express & Suites Amarillo West, an IHG Hotel
  • Attractions of Note: It’s quiet stretch of desert between Tulsa and Amarillo, Texas. But you won’t want to miss the official half-way point of the Mother Road in Adrian, Texas. The Midpoint Cafe and Gift Shop isn’t to be missed -be sure to try some pie! In Amarillo, step back in time at the Cadillac Ranch and witness a unique art installation featuring vintage Cadillacs buried nose-down in the ground. For dinner, indulge in a true Texan dining experience at the legendary Big Texan Steak Ranch (make reservations ahead of time).
TeePee Curios, Tucumcari

Day Five

  • Start: Amarillo, TX
  • Stop: Albuquerque, NM
  • Miles/Hours on Road: 343 miles, 5 hours, 18 minutes
  • Lodging: Hotel Albuquerque at Old Town or Hotel Chaco
  • Attractions of Note: Be sure to visit the Blue Swallow Motel and TeePee Curios in Tucumcari, New Mexico. En route to Albuquerque, detour to Santa Fe, and lose yourself in the whimsical world of Meow Wolf’s House of Eternal Return, where art and imagination collide. In Albuquerque, explore the historic Old Town and savor the flavors of authentic Southwestern cuisine.
Jackson Browne Statue on the Corner in Winslow, Arizona

Day Six

  • Start: Albuquerque, NM
  • Stop: Kingman, AZ
  • Miles/Hours on Road: 469 miles, 6 hours, 55 minutes
  • Lodging: Holiday Inn Express Hotel & Suites Kingman, an IHG Hotel
  • Attractions of Note: Traverse the rugged landscapes of Arizona and make a detour to witness the famous corner in Winslow immortalized in the song “Take it Easy” by Jackson Browne. While you’re there, have lunch at The Turquoise Room at La Posada Hotel. Continuing your journey, enjoy the elevation and natural beauty of Flagstaff on a short hike. Finally, have dinner at the world famous Road Kill Cafe in Seligman before reaching Kingman for the night.
Ens of Route 66 Sign, Santa Monica Pier

Day Seven

  • Start: Kingman, AZ
  • Stop: Santa Monica, CA
  • Miles/Hours on Road: 336 miles, 5 hours, 15 minutes
  • Lodging: Gateway Hotel Santa Monica
  • Attractions of Note: The last day on the Mother Road is one to remember. Along the way, we pass through Needles, the boyhood home of Charles Schulz, and the Mojave National Preserve, one of the driest places on the planet. As we traverse Route 66 across Los Angeles, including California’s first freeway, Hollywood, and Sunset Boulevard, we finally arrive at our destination, ready to bask in the glory of our cross-country adventure. Take in the sights and sounds of the iconic Santa Monica Pier, including a photo with the Route 66 End of Route Sign, before bidding farewell to the Mother Road.

Ready to experience the magic of Route 66 for yourself? Reach out and let us help you book your own trip down this historic highway. Whether it’s a solo adventure or a family road trip, we’ll ensure your journey is filled with unforgettable memories.


Sail with Us: Featured Cruises for the Adventurous Souls

Join us on a voyage of discovery as we set sail on three specially curated cruises, designed to ignite your sense of adventure and create lasting memories.

7-Nights Alaska Southbound Glacier Cruise on Celebrity Summit: Traverse the breathtaking landscapes of Alaska from Seward, Alaska to Vancouver, British Columbia in July 2024. Let the rugged beauty of the Last Frontier captivate your soul. See the full itinerary here. Rooms starting around $2200. Call or email us to book!



Resilient New Year’s Ahoy on Virgin Voyages: Welcome the new year in style on a luxurious 7-night cruise departing from San Juan, Puerto Rico, from December 28 to January 4. Explore the vibrant cultures and stunning landscapes of the Southern Caribbean (Virgin Islands, Barbados, Saint Lucia, Antigua and Barbuda, and Sint Maarten) as you sail into 2025! Rooms starting around $3800. Call or email us to book! Or use this link to book on your own.


Southern Spain & Casablanca on Virgin Voyages: Experience the allure of the Mediterranean on a captivating 10-Night journey onboard Scarlet Lady from Barcelona to Ibiza, Palma de Mallorca, Valencia, Malaga, Cadiz, Casablanca, and back. Let the azure waters and ancient wonders of the Mediterranean mesmerize your senses. This trip isn’t one to miss. Rooms starting around $4414. Call or email us to book! Or use this link to book on your own.


Stay tuned for more exhilarating travel insights and recommendations in our upcoming edition of Journeys Shared. Until then, happy travels and may your adventures be as boundless as your dreams! 🚢🌍

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