• Route 66

Route 66 Holidays

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 recognisable 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.

Duration
16 days
Options
Private basis, Self-Guided
Start your journey

Trip highlights

  • 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

Arrive at Chicago's O'Hare International Airport make your way to your hotel and let your adventure begin. Experience mile after magnificent mile of the Windy City. Stand on the corner of Michigan and Adams, marked as the starting point of Historic Route 66. Enjoy coffee and a big breakfast at Lou Mitchell's, a Chicago institution since 1923 and a must for Route 66 travellers. Stroll the lakefront, peruse the shops, bike the parks, grab a Chicago Dog, or explore the city's incredible sights and architectural treasures including Willis Tower, one of the tallest buildings in North America.

Suggested Accommodation

  • The Whitehall Chicago or similar

This morning, pick up your rental car and get ready for an unforgettable journey into the then and now of America along Historic Route 66. This legendary old road passes through a variety of pure Americana landscapes and takes in some of the country's biggest, oldest and most peculiar sites along the way. Begin your journey by following the traditional east-to-west path of Route 66 from Chicago to St. Louis, Missouri, cruising through endless cornfield and flat prairies. En route, don't miss Wilmington's most photographed "citizen", the larger-than-life green Gemini Giant, and Atlanta's Bunyan Giant, a 19-foot statue of Paul Bunyan holding a giant hot dog. In Springfield, stop at the Cozy Dog Drive-In, the birthplace of the corn dog, and explore the legacy of Abraham Lincoln with a visit to the Lincoln Home National Historic Site. Once in St. Louis, the largest city along Route 66, you can follow in the footsteps of legendary explorers by visiting the historic sites found throughout the city, including the Gateway Arch, the nation's tallest monument.

Suggested Accommodation

  • The Hotel Majestic St. Louis or similar

Continue through the Ozark Highlands of southern Missouri to Springfield, recognized as the birthplace of Route 66. En route, stop at Meramec Caverns, an extensive set of natural limestone caves whose formations and colours are as unique as they are beautiful. Adding to the pleasure of exploring the caves is learning that Jesse James used them as a hideout and took advantage of the underground river to escape through the back door.

Suggested Accommodation

  • Best Western Route 66 Rail Haven or similar

This morning, cut through the south-eastern corner of Kansas on your way to Oklahoma City. The Oklahoma section of Route 66 contains more drive-able miles than any other state as well as several miles of the original 9-foot road segment that served Oklahoman families headed west in search of better opportunities during the 1930's. En route to Oklahoma City, stop to view the beloved 20-foot tall cement Blue Whale in Catoosa, a landmark along Route 66, and the Cyrus Avery Route 66 Memorial Bridge in Tulsa honouring the Father of Route 66's memory and connection to the historic highway. Once in Oklahoma City, the state's capital, be sure to check out the old Route 66 motels, gas stations and numerous vintage buildings.

Suggested Accommodation

  • Sheraton Oklahoma City Downtown Hotel or similar

Continue to Amarillo, located in the pancake-flat plains of the Texas Panhandle. This area of Texas was once the buffalo-rich grasslands of the Great Plains, inhabited by bands of Kiowa and Comanche Indians. Stop at the Route 66 Museum in Clinton where you experience six decades of Route 66 history. See Shamrock's Tower Station and the U-Drop Inn Cafe whose towering spire is still a reminder of the booming business it once saw. See the first restored Phillips 66 gas station in McLean and in Groom, the leaning water tower and a 150-foot tall stainless steel cross. Once in Amarillo, be sure to stop at Big Texas Steak Ranch where you can attempt their 72oz. steak challenge.

Suggested Accommodation

  • Holiday Inn Express Hotel & Suites Amarillo or similar

Before leaving Amarillo be sure to visit Cadillac Ranch. This unique display of art features a row of ten colourfully painted Cadillac cars buried grille first in the ground. Continue to the MidPoint Cafe in Adrian famous for its Ugly Crust pies. From Adrian you'll follow Route 66 to Albuquerque, New Mexico for a great taste of the Land of Enchantment.

Suggested Accommodation

  • Best Western Plus Rio Grande Inn or similar

The state's largest city, Albuquerque spreads north and south along the banks of the Rio Grande. Spend the day exploring Downtown Albuquerque's Central Avenue, a treasure trove of Route 66 landmarks. Historic Old Town offers a taste of New Mexico's Spanish colonial past while the Indian Pueblo Cultural Centre, owned by the state's 19 different Pueblo communities, traces the history of the region's Native American cultures.

Suggested Accommodation

  • Best Western Plus Rio Grande Inn or similar

To get a true sense of the Old Route 66, today you will detour to New Mexico's state capital, Santa Fe. Founded on the ruins of an abandoned Indian village and steeped in history, Santa Fe is the oldest capital in the U.S., and although it lost its place on Route 66 in 1938, it remains one of the most picturesque cities in the state. At one time this was the end of the old Santa Fe Trail, the earliest trade route linking the American frontier back east with the far west. Plan to visit one of Santa Fe's famous art galleries, art markets, or museums full of traditional and contemporary art, including works by their own Georgia O'Keeffe, or shop for authentic creations you just won't find anywhere else.

Suggested Accommodation

  • Best Western Plus Rio Grande Inn or similar

This morning, the state of Arizona welcomes Route 66 travellers with an overwhelming display of trading posts. View huge concrete tepees that stand at the foot of brilliant red-rock mesas en route to Petrified Forest National Park, the only park in the National Park System containing a section of Historic Route 66. Here you will come face-to-face with over 13,000 years of human history and one of the world's largest and most colourful assemblies of petrified wood, historic structures and archaeological sites. Catch a sunset over the Painted Desert from the park's Kachina Point before heading to Holbrook. Once in Holbrook, stop at the Wigwam Motel whose steel and concrete tepees featuring modern conveniences have welcomed guests since the 1950's.

Suggested Accommodation

  • Magnuson Adobe Inn or similar

Continue to Meteor City, a true vintage trading post whose distinctive dome can be seen for miles along this stretch of Route 66. Pass through Flagstaff and Williams en route to Grand Canyon National Park, a natural wonder that you simply have to see to believe. Spend the day discovering the distinct South Rim of the Canyon. Stop at one of the numerous overlooks, walk part of the Rim Trail or along the historic Hermit Road. Visit a Photo Hot Spot, or climb to the top of a stone Watchtower for panoramic views that extend over 100 miles on clear days.

Suggested Accommodation

  • Grand Canyon Railway Hotel or similar

Leave the town of Williams and the Grand Canyon behind as you make your way to Seligman, the first stop heading west on the longest uninterrupted stretch of Route 66. Continue through Kingman whose old Route 66 cafes and motels still flourish, to one of Arizona's hidden treasures, Hoover Dam. Considered the largest single public works project in the history of the U.S., Hoover Dam straddles the mighty Colorado River, which forms the border between Nevada and Arizona and brings much-needed water and power to the Southwest. Continue to Las Vegas, Nevada, a city that needs no introduction.

Suggested Accommodation

  • Luxor Hotel & Casino or similar

Enjoy a full day Las Vegas style. Walk the famous Strip lined with mega-resorts and flashing neon lights, place a bet at one of the many casinos, dine at world-class restaurants, catch the latest must-see show, shop designer boutiques, ride a roller coaster, lay by the pool... the list goes on. With so much to do, 24 hours in a day hardly seems like enough.

Suggested Accommodation

  • Luxor Hotel & Casino or similar

This morning, set out through the Mojave Desert for Calico Ghost Town, California's authentic silver mining town and one of the few original mining camps of the Old West. Re-join Route 66 in Barstow where a collection of historic photographs and artifacts related to Route 66 and the Mojave Desert Communities are on display at the Route 66 Mother Road Museum. Continue through Pasadena, Los Angeles, West Hollywood and Beverly Hills to Santa Monica for a true Hollywood ending to your cross-country journey. Park and venture the last few blocks on foot to view the End of the Trail sign on Santa Monica's Pier. This sign officially marks the western end of Historic Route 66.

Suggested Accommodation

  • Hilton Anaheim or similar

Spend the day strolling along the beaches of Santa Monica or browsing the adjacent indoor/outdoor shops at Third Street Promenade. Or, further explore L.A.'s one-of-a-kind destinations, playgrounds of the rich and famous and architectural gems. Universal Studios Hollywood and Anaheim's original Disneyland Park are also located within easy driving distance. You will be staying for your last two nights in Anaheim, but talk to our destination specialists about extending your trip with a wonderful beach stay in Santa Monica. This cool and captivating coastal city is the perfect end to a driving holiday across America. Ride the Ferris wheel on the pier, do some shopping at Santa Monica Place or simply dip your toes into the soft sand and relax while soaking up the gorgeous sunshine.

Suggested Accommodation

  • Hilton Anaheim or similar

Included

  • International flights
  • 15 nights hotel accommodation
  • Room only
  • Car hire and basic car insurance

Not included

  • One way drop car hire fees (if applicable)
  • Meals or excursions unless specified
  • Park entrance fees (if applicable)