Route 66

16 day self drive itinerary

Route 66 Holidays

Three time zones, one holiday, one country

We love talking holidays and we're here to help. If you'd like our advice on how to create an amazing Chicago holiday, just give our Destination Specialists a call.

Route 66 has to be on everyone's wish list and so let us make those wishes come true. 

Established back in 1926, famously known as Route 66 and covering a total of 2,448 miles across eight states, this journey will take you from Chicago all the way to California. Before the U.S Highway System was put in place you would have been able to drive the whole route on just one road, used by many when migrating over to the west many a business grew from the highways popularity and on certain roads you can still enjoy these historic businesses. Of course, over time, improvements and developments changed the original road to what we see today but many portions of the road are still in existence and known as Historic Route 66.

Beginning in the windy city of Chicago where the road originally started, driving down through to St Louis, Missouri where you will be sure to see some recognizable landmarks from TV shows, through Springfield, Tulsa and then on to Oklahoma City which boasts the longest of the original road segment. From Oklahoma "your on your way to Amarillo" in the Texas panhandle and then on to get a taste of New Mexico. You will pass an overwhelming amount of trading posts as you drive on through Arizona and then marvel at the sights in Grand National Park before heading to the neon lights and fun of Las Vegas. From Las Vegas you will head to Santa Monica where the road ends but get your camera ready and be sure to capture the sign marking the end of the road. A journey not to be missed.

Our Experts Recommend:
  • Why not hire a convertible? Motorcycle? or even travel Route 66 by Motorhome?
  • Gaze at Chicago's Willis Tower, the tallest building in North America
  • Take a pit stop at the Cadillac Ranch; camera at the ready
  • Stop at the Route 66 museum in Clinton and learn about the history of Route 66
  • Take in a movie at the 66 Drive-In theatre in Missouri
  • View one of the Seven Natural Wonders of the World, the Grand Canyon

Sample Itinerary Summary

Not quite your cup of tea? Our Destination Specialists can tailor any part of this itinerary or create one from scratch just for you.

16 days
Destination Breakdown
Private basis, Self-Guided
  • International flights
  • 15 nights hotel accommodation
  • Room Only
  • Car hire and basic car insurance
Not included
  • Car insurance upgrade (please contact our destination specialists to upgrade)
  • Meals or excursions unless specified
  • Park entrance fees (if applicable)
  • Chicago

    Itinerary Highlights

    • Take a boat cruise or take a stroll along the Chicago River
    • Go shopping along the vibrant Magnificent Mile
    • Get your camera ready for the mirrored shot of you in Cloud Gate
    • Walk to the Navy Pier and dine, shop and enjoy the carnival rides
    • Take an appetite with you, enjoy some amazing cuisines
  • St Louis

    Itinerary Highlights

    • This is the largest city along Route 66
    • Get a birds eye view of the Gateway Arch
    • A multitude of soulful music in restaurants and brewery's
    • Head to Ballpark Village and soak up the atmosphere where every sport is celebrated
    • Galleries, Museums, Brewery tours and Cathedrals to explore and enjoy
  • Springfield

    Itinerary Highlights

    • Known as the birthplace of Route 66
    • Considered the gateway to the great outdoors; see the beauty of the Ozarks in one of the many pristine parks
    • Explore great wineries and vineyards
    • A wide range of museums to take in
    • Don't miss a stroll around the farmers market (everyday)
  • Oklahoma

    Itinerary Highlights

    • Take in the old Route 66 motels, gas stations and numerous vintage buildings
    • From boutique quirky shops to outlet shopping you must do some retail therapy
    • Always ready for a night on the town, head to Bricktown Entertainment District
    • Visit the Buffalo Bill statue and learn the history at the National Cowboy and Western Heritage Museum
    • Enjoy the sites of Oklahoma's entertainment district on the Bricktown Water Taxi, running all day
  • Texas

    Itinerary Highlights

    • In Amarillo stop at the ritual site on The Mother Road, Cadillac Park
    • Stop at the Big Texan Steak Ranch and take on the 72oz challenge
    • Before leaving Texas stop at the Midpoint of your journey in Adrian - don't forget to take a picture
    • Have a western adventure tour at "Cowgirls and Cowboys in the West"
    • A must before you leave is a hike or bike around Palo Duro Canyon State Park
  • New Mexico

    Itinerary Highlights

    • Explore Albuquerque's downtown Central Avenue and see historic Route 66 landmarks
    • Historic Old Town offers a taste of New Mexico's Spanish colonial past
    • State capital, Santa Fe, one of the most picturesque cities in the state
    • Santa Fe is ranked as the country's third largest art market
    • Take in lunch in this food lover's paradise and you will be asked "Red or Green?", referring to what chilli!
  • Utah & Arizona

    Itinerary Highlights

    • In Holbrook stop at the Wigwam Motel with steel and concrete teepees
    • Steeped in Native American culture, Holbrook began as a town of railroaders, cattlemen, outlaws and rugged lawmen
    • Take the day to explore the distinct South Rim of the Grand Canyon National Park
    • Climb to the top of a stone Watchtower for panoramic views of the canyon
    • Take in the hidden treasure of the Hoover Dam
  • Las Vegas

    Itinerary Highlights

    • Walk the famous Strip and take in the bustling atmosphere and sights
    • Take lunch at one of the bars opposite the Bellagio and enjoy the famous fountain display
    • Head to the Mob Museum and learn about the organised crime of Las Vegas history
    • Don't leave without walking along Freemont Street - great bars, restaurants and people
    • Home to many spectacular shows and concerts not to be missed
  • Los Angeles

    Itinerary Highlights

    • See the replica of the long-lost Route 66 "End of the Trail" sign at the Santa Monica Pier
    • Relax on the beach of Santa Monica or browse the shops at Third Street Promenade
    • Playground to the rich and famous go to Rodeo Drive and take in a spot of lunch at the Ivy
    • Visit Universal Studios Hollywood and the original Disneyland Park
    • Take in a Hollywood landmark and vist the Grayman's Chinese Theatre