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21 Days Historic Route 66 Fly Drive Holiday

21 days from £1,799pp

Chicago - St Louis - Springfield - Oklahoma City - Amarillo - Albuquerque – Santa Fe - Holbrook - Grand Canyon – Anaheim - Santa Monica - Los Angeles

With extra time built-in for sightseeing and breaks from driving, this well-balanced fly-drive itinerary following iconic Route 66 from Chicago to Santa Monica Pier will be a once-in-a-lifetime experience. Your journey will take you over 2,400 miles through the contrasting landscapes of the USA, with the famous quirky Route 66 landmarks to visit along the way.

If you're looking for a shorter trip, check out our 16 day Route 66 fly drive holiday itinerary.

Holiday Highlights

  • Take in the iconic skyscrapers and blue-green rivers of Chicago.
  • Sample some of America’s most famous diners and bizarre roadside attractions.
  • Go for a hike or stop at one of the many roadside view points at the Grand Canyon, one of the seven natural wonders of the world!

Remember, we can tailor-make your fly drive holiday to suit your needs, including car rental with our trusted car hire partner Alamo. You can contact our travel experts today on 0208 290 9751.

Holiday Map

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Detailed Itinerary

Day 1: London to Chicago

Arrive at Chicago’s O’Hare International Airport, your starting destination to begin your epic Route 66 journey. On arrival, transfer independently to your hotel. Stay 2 nights at Chicago’s Essex Inn (or similar).

Day 2: Chicago

Step outside today and 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, browse the shops, bike the parks, grab a Chicago Dog, or explore the incredible sights and architectural treasures including the impressive skyline views at the Willis Tower.

Day 3: Chicago - St Louis (approx. 296 miles)

Today, pick up your Alamo rental car from the depot to start your drive along Route 66. Begin your journey by following the traditional east-to-west path of Route 66 from Chicago to St Louis. En route, 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. Stay 2 nights at the Red Roof Inn St. Louis (or similar).

Day 4: St. Louis

A day at leisure to explore the best of St. Louis. First stop will be a visit the Gateway Arch, the tallest monument in the USA, for its breathtaking views. Be sure to take a tour of one St Louis' many local breweries or spend the afternoon strolling the interesting boutiques on the Delmar Loop.

Day 5: St. Louis – Springfield (Missouri) (approx. 210 miles)

Continue through the Ozark Highlands to Springfield, Missouri, recognised as the birthplace of Route 66 in 1926. En route, be sure to stop at Meramec Caverns in Stanton, 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 their “back door”. Stay 2 nights at the Best Western Route 66 (or similar).

Day 6: Springfield (Missouri)

A full day at leisure to explore Springfield Missouri, known as the Queen City of the Ozarks and the birthplace of Route 66. Visit the city’s Discovery Center, great for adults and children alike, or perhaps relive some childhood memories at the 1984 vintage video games arcade. South-east of the city lie the beautiful Ozark mountains.

Day 7: Springfield - Oklahoma City (approx. 310 miles)

This morning, travel south-west via Kansas, the shortest stretch of Route 66's eight-state run on your drive to Oklahoma City. Along the way, stop to see many of the famous Route 66 landmarks such as the Blue Whale in Catoosa, Oilman Driller in Tulsa, Route 66 motels and gas stations in Stroud & Chandler, POPs and the Round Barn in Arcadia, and the Milk Bottle in Oklahoma City. Once in Oklahoma City, the state’s capital, be sure to check out the numerous vintage buildings and maybe consider Ann’s Chicken Fry House as the place for a delicious chicken fried steak dinner. Stay 1 night at Howard Johnson Express Inn (or similar).

Day 8: Oklahoma City - Amarillo (approx. 260 miles)

Continue through Oklahoma to Amarillo, located in the flat plains of the Texas Panhandle, stopping en route at the Route 66 Museum in Clinton where you can experience six decades of Route 66 history and at U-Drop Inn Café, 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 visit Big Texas Steak Ranch where only the very hungry should attempt their 72oz. steak challenge. Stay 2 nights at the Quality Inn Medical Center (or similar).

Day 9: Amarillo

A day at leisure to explore Amarillo, which offers a true western heritage and wide open spaces. Spend time at the American Quarter Horse Hall of Fame which honours all things equestrian or at the Amarillo Art Museum. There are many ranches to spend visit in this area, such as the Silver Mesa ranch, which offers horseback rides, horse-drawn wagons, old-west gunfights and cowboy meals.

Day 10: Amarillo - Albuquerque (approx. 270 miles)

Before leaving Amarillo visit the Cadillac Ranch, where you can see a unique display of art featuring a row of ten colourfully painted Cadillac cars buried grille first in the ground. Continue to the MidPoint Café in Adrian, located at the halfway point of Route 66 and famous for its “ugly crust” pies. From Adrian, follow Route 66 to Albuquerque in New Mexico for a great taste of the Land of Enchantment. Stay 2 nights at the Best Western Plus Rio Grande Inn (or similar).

Day 11: Albuquerque

Located virtually in the centre of New Mexico, Albuquerque spreads north and south along the banks of the Rio Grande and is by far the state’s largest city. Spend the day exploring Central Avenue, a treasure trove of Route 66 landmarks and one of the original Route 66 towns. Historic Old Town offers a taste of New Mexico’s Spanish colonial past while the Indian Pueblo Cultural Center, owned by the state’s 19 different Pueblo communities, traces the history of the region’s Native American cultures.

Day 12: Albuquerque – Santa Fe (approx. 65 miles)

To get a true sense of the Old Route 66, continue to Santa Fe, the oldest capital in the US. 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 a visit to one of Santa Fe’s famous art galleries and museums full of traditional and contemporary art including works by their own Georgia O’Keefe, or shop for authentic creations you just won’t find anywhere else. Stay 1 night at the Courtyard by Santa Fe (or similar).

Day 13: Santa Fe - Holbrook (approx. 294 miles)

Travel to Holbrook via the Petrified Forest National Park, the only National Park containing a section of 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 colorful assemblies of petrified wood, historic structures and archeological sites. At the park, catch the sunset over the Painted Desert from Kachina Point. Once in Holbrook, stop at the Wigwam Motel whose steel and concrete tepees feature modern conveniences and have been welcoming guests since the 1950’s. Stay 1 night at Magnuson Adobe Inn (or similar).

Day 14: Holbrook to Grand Canyon/Williams (approx. 180 miles)

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, where you can 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 climb to the top of a stone Watchtower for panoramic views that extend over 100 miles on clear days. Stay 2 nights at the Grand Canyon Railway Hotel (or similar).

Day 15: Grand Canyon/Williams

More time today to enjoy the truly awesome sights of the Grand Canyon, especially the dramatic sunrises or sunsets reflecting on the canyon walls. Perhaps leave the car behind today and take a ride on the scenic Grand Canyon Railway from Williams to the Grand Canyon rim and be entertained along the way by the music and commentary on board.

Day 16: Williams to Las Vegas (approx. 300 miles)

Leave the town of Williams 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 cafés and motels still flourish today, then on to one of Arizona’s famous treasures, the 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. Your journey today ends in Las Vegas, a city that needs no introduction. Stay 2 nights at the Excalibur Hotel (or similar).

Day 17: Las Vegas

Enjoy a full day to explore the famous Strip, with its 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 rollercoaster, lay by the pool… the list goes on. With so much to do, 24 hours in a day hardly seems like enough.

Day 18: Las Vegas to Anaheim, Los Angeles (approx. 264 miles)

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 artefacts are on display at the Route 66 Mother Road Museum. Continue through Pasadena and Los Angeles to Anaheim. Stay 2 nights at the Quality Inn & Suites Anaheim (or similar).

Day 19: Anaheim

Spend the day at Disneyland enjoying the delights of this wonderful theme park. Or, why not further explore the Los Angeles area with Hollywood, Beverly Hills, Universal Studios Hollywood all located within easy driving distance.

Day 20: Anaheim to Santa Monica (approx. 42 miles)

The final leg of Route 66 awaits today towards Santa Monica for a true Hollywood ending to your cross-country journey. Park and walk the last few blocks to view the “End of the Trail” sign on Santa Monica's Pier. Spend the day strolling along this lively town’s beaches or browsing the trendy and boutique shops along Third Street Promenade. Stay 1 night at the Best Western Plus Gateway Santa Monica.

Day 21: Santa Monica to Los Angeles International Airport (approx. 10 miles)

Enjoy more of Santa Monica this morning before returning your rental car at Los Angeles International Airport prior to your departure flight to London.

(read more...)


Included in your Fly Drive Holiday

  • Hotel accommodation
  • Economy flights
  • Airport taxes, fuel & duty
  • Car rental where stated
  • Any applicable offers

Not included: Airport transfers,car hire one-way drop off fees, meals, sightseeing, entry fees & personal expenses.

Flights from regional UK airports available

Remember, we can tailor-make your holiday to suit your needs, contact our travel experts today, call us on 0208 290 9751.

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