Route 66 Holidays

Days 1 - 2 : Chicago, Illinois

Every Route 66 journey starts in Chicago. The road originally began at the corner of Jackson and Michigan Boulevards in 1926, although parts of the highway have been in existence since 1857 when the US War Department order a government funded wagon road across the desert. Later the Lone Star Route connected Chicago and St. Louis and the National Old Trail Roads traced a path between St Louis and Los Angeles. Ultimately all these roads were connected into one to become Route 66.

Poet Carl Sandburg described Chicago as the City of the Big Shoulders in 1916, and the city carries that moniker proudly to this day. With world-class museums and cultural attractions alongside thriving commercial and industrial ventures, Chicago hums with energy. Be sure to visit the Shedd Aquarium, Art Institute of Chicago, Adler Planetarium, John Hancock Observatory, Magnificent Mile, Millenium Park and Navy Pier. Don't forget also to visit the The Ledge at the WIllis Tower, it's America's tallest building and the views across Chicago are amazing.

Chicago is considered the birthplace of the skyscraper. To capture the beauty of these, take the Chicago’s First Lady Architecture Cruise which follows the Chicago River and highlights the design and architectural achievements of over 50 buildings along its course. If you're feeling a bit energetic hire a bike and enjoy a ride along the 26 miles of uninterrupted coastline around lake Michigan.

To make the most of your short time in the Windy City let Bon Voyage pre-book excursions for you. We've a host of experiences from lake cruises to Blues Club evenings that we know you'll enjoy.

Day 3 : Springfield, Illinois

Distance: 198 miles

As you set off on your Route 66 adventure and travel from Chicago via Springfield to St Louis, the icons of Route 66 will start to appear.

Two hundred miles south of Chicago is Springfield, Illinois. Springfield became the Illinois state capital in 1837 with the help of a young lawyer and politician named Abraham Lincoln. He lived in the city until he left to become the 16th President of the United States, in 1861. From that moment on, the city’s history and future have been inexorably tied to this most famous and beloved American citizen. Not surprisingly, the city of Springfield is dotted with sites dedicated to his memory. These include: the Lincoln Home National Historic Site, the Lincoln-Herndon Law Offices, the Lincoln Tomb, the Old State Capitol State and the Abraham Lincoln Presidential Library and Museum.

On February 10, 2007 President Barack Obama announced his presidential candidacy in Springfield, standing on the grounds of the Old State Capitol. A historically significant place in America today.


Route 66 passes through the heart of Springfield and is home to two very famous Route 66 landmarks past and present. Sadly, Bill Shea, owner of Shea’s Gas Station Museum passed away in December 2013 and the museum is currently closed. We are hopeful it will be up and running again soon. Meanwhile, the Cozy Dog Drive In is open and ready for business. A hotdog on a stick is a Route 66 must. For a truly authentic Route 66 experience - head to the Route 66 Drive-In Theatre and watch the latest blockbuster from the comfort of your front seat. 

Day 4 : St Louis, Missouri

Distance: 101 miles

Today you'll cross from Illinois to Missouri by way of the historic Martin Luther King Memorial Bridge. Saint Louis in the 'Show Me' State of Missouri is the largest city you'll encounter between Chicago and Los Angeles. There are a number of cool sites related to the Mother Road in this region. 

One-of-a-kind is practically St Louis middle name – from the hundreds of unique eateries (our favourite is Sweetie Pies) and dining options to the 'only in St. Louis' attractions like Anheuser-Busch Brewery, the Loop Neighborhood, the Gateway Arch and City Museum. No one else can claim the delicious concretes at historic Ted Drewes Frozen Custard stand on historic Route 66, or replicate the hottest blues clubs. 

Day 5 : Branson, Missouri

Distance: 252 miles

En route to your next destination, Branson, be sure to stop at Meramec Caverns. Possibly the oldest stop on Route 66, these huge caves are reputed to have been used as the hideout for Jesse James and his gang. Guided tours are available.

Branson is a short detour off Route 66 and is nestled in the lakeside beauty of the Ozark Mountains. This lively, fun town is known as The Live Music Show Capital Of The World. Over a 100 shows run daily here morning, noon and night, so you'll be sure to see something that takes your fancy. Enjoy the sounds of the 50s and 60s in Dick Clark's American Bandstand, see some of the world's best tributes in the Legends In Concert show, take in an Elvis extravaganza, or tap your toes to an good old Country and Western show. American kitsch as its best. 

Day 6 : Tulsa, Oklahoma

Distance: 221 miles

Entering Oklahoma from Missouri, you strike out on the longest driveable section of Route 66. Here you'll experience the restless history of America - 200 years of tracks, trails and roads charting the settlers’ exodus from east to west; the cattle drives from south to north; the endless wandering of native american tribes, and the unstoppable progress of the Mother Road. Towards Tulsa, the typically Oklahoman township of Vinita and the legendary diner - Clanton’s Cafe - will set the scene for the coming days.

Your overnight Route 66 holiday stop is in Tulsa - an eclectic mix of Oklahoma’s trademark friendliness; great food; a vibrant music scene; art and history in a compact, strolling city. Cherry Street and Brady Street are for wandering and the Philbrook and Gilcrease Museums are for browsing world and American art.

Day 7 : Oklahoma City, Oklahoma

Distance: 107 miles

Between Tulsa and Oklahoma City, the Mother Road offers up endless attractions - Chandler’s fascinating Route 66 Interpretive Center; the intriguing Seaba Station Motorcycle Museum; Arcadia’s fine Round Barn and fun POPS store, to name just a few.

Utterly and astoundingly re-vitalised in the past 30 years, Oklahoma City hums with optimism and activity. Visit the University area in Norman and the superb National Cowboy & Western Heritage Museum, and in the evening stroll around Bricktown - newly alive with eating places and bars, shops and music venues.

Heading for the state line from Oklahoma City, your Route 66 experience becomes ever more potent. On this stretch you will encounter the Mother Road on a working day; the 3 famous diners of El Reno - Robert’s, Sid’s and Johnnie’s; the unmistakable Lucille’s at Weatherford, and the Mohawk Lodge Indian Store at Clinton. Here, the Oklahoma Route 66 Museum, and at Elk City - the National Museum, are must-sees - the latter also for a fascinating insight into small town life in the 1800’s.

If you'd like to experience a Ranch stay on your Route 66 holiday, speak to the friendly team of USA experts at Bon Voyage about a detour from Oklahoma City to Texas and the Wildcatter Ranch.

Day 8 : Amarillo, Texas

Distance: 258 miles

Leave Oklahoma behind and cruise into the Lone Star State, Texas. This stretch of your Route 66 holiday in the Texas Panhandle provides not only a number of vintage Main Street America icons as you travel across the Staked Plains but also glimpses of the true Wild, Wild West. Here it becomes obvious that a profound change is occurring. You'll have left the Midwest clearly behind and begun to experience the wide open spaces of The West.

This is the heart of Cowboy Country. Here too, you will find the Texas icons of Route 66 start appearing, such the Rattlesnake Ranch, The Barbed Wire Museum, the Cadillac Ranch and the U Drop Inn.

Outside Amarillo you will find vast ranches of the Texas Panhandle, some numbering in the millions of acres that spread as far as the eye can see. Shortly after being discovered by the Spanish Explorer Francisco Coronado in 1541, the area became a magnet for cattlemen and sheep herders from all points of the compass looking for fresh grazing grounds. Some Dust Bowl farmers headed to California while others stopped here to stake their claim for ranching. As a result, Amarillo still has a unique blend of the Old West and the New West, populated by American Cowboys, roughnecks, self made millionaires and the ever present oil derricks. Make sure you allow time to drive Amarillo Boulevard which is part of the original Route 66. The road is lined with block after block of strip shopping centres and roadside motels straight out of the 1950s.

If you're a Buddy Holly fan you may wish to consider a detour from your Route 66 holiday to Lubbock, Texas, home of Buddy Holly. 

Day 9 : Tucumcari, New Mexico

Distance: 112 miles

On your your Route 66 holiday between Amarillo, Texas and the New Mexico border, you'll encounter the town of Adrian. This is the geographical midpoint of Route 66. The Midpoint Cafe here is one of the route's most enjoyable place to eat. Order the Ugly Crust Pie, a true Route 66 delicacy.

En route to your next stop you'll encounter one of Route 66's most famous stops - the Cadillac Ranch. It was invented and built by a group of art-hippies imported from San Francisco. They called themselves The Ant Farm, and their silent partner was Amarillo billionaire Stanley Marsh III. He wanted a piece of public art that would baffle the locals, and the hippies came up with a tribute to the evolution of the Cadillac tail fin.Be sure to bring along a can of spray paint and create your own art on one of these Cadillacs. It makes for a great kodak moment.

Your overnight stop today on your Route 66 fly-drive is Tucumcari. Here you can visit the Mesalands Community College Dinosaur Museum, a first-class museum housing the world's largest collection of spectacular full-scale bronze dinosaur skeletons. To find out about the history of Tucumcari and Route 66, stop by the Tucumcari Historical Museum with its story-telling like exhibits, including a Route 66 exhibit. Be sure to get your picture taken in front of the Route 66 Roadside Attraction at the Convention Center or the world's largest mural devoted to Route 66 in the United States. At night Tucumcari comes alive with those famous vintage Route 66 Neon signs. 

Day 10 - 11 : Santa Fe, New Mexico

Distance: 167 miles

Your stop for the next two nights is in historic Santa Fe, one of the original abandoned routings of Route 66.

Boasting 320 days of sunshine a year, colourful Santa Fe is the capital of the state of New Mexico (in fact, the oldest state capital in the USA) and the very embodiment of a south-western city with its pueblo-style buildings, numerous galleries and superb museums. Life here revolves around the charming and historic Sante Fe Plaza. Park up, find a cafe on the Plaza, grab a margarita on the rocks and watch the world go by in one of the most fascinating cities in the USA.

Whilst you're in Santa Fe be sure to visit Museum Hill which has a collection of four of Sante Fe's most interesting museums. Santa Fe is ranked the second largest art market in the United States and Canyon Road has the highest concentration of art galleries in the US. If you love food they you'll be in seventh heaven here with over 200 restaurants to choose from. And, if you're a fan of the opera you're in for a treat, the world-class Santa Fe opera has its home here.

Day 12 - 13 : Durango, Colorado

Distance: 212 miles

En route to your next stop (and a total detour from Route 66) consider a visit to historic Taos in the base of the Sangre De Cristo Mountains, or a part drive along the Enchanted Circle scenic drive, both are north of Santa Fe.

Next stop the state of Colorado. You’ll simply adore Durango. This scenic Colorado mountain town is nestled at the south-western foot of the Rocky Mountains in the Four Corners region. It’s surrounded by the 2 million-acre San Juan National Forest and enjoys 300 days of sunshine per year. You'll love strolling around the historic Western downtown area with its wide choice of restaurants, galleries and eclectic boutiques. Here we'd encourage you to experience the Rocky Mountains on board the famous Durango and Silverton Narrow Gauge Railroad. Revel in the sights and sounds of a bygone era as the train winds through 46 scenic miles of the San Juan National Forest to the old mining town of Silverton, Colorado. This spectacular journey can be pre-booked in advance with Bon Voyage.

Day 14 : Monument Valley

Distance: 212 miles

Leave verdant Colorado behind today and head for one of the most magical places in  the USA, Monument Valley. En route to Monument Valley, if time allows, you may wish to stop at Mesa Verde National Park, Colorado. This is a world UNESCO site and is the largest archaeological preserve in the United States.

Monument Valley is located along the Utah/Arizona border towards the southeast corner of Utah. Whether or not you are aware of it, you have very likely already seen Monument Valley in countless Western movies and television programmes. It is claimed by some to be legendary Hollywood director John Ford’s favourite movie backdrop. Famous movies that have been filmed here include The Lone Ranger, Stagecoach, She Wore A Yellow Ribbon, Transformers, Fort Apache, How The West Was Won, Billy The Kid and Rio Grande. 

Monument Valley is an area of monolithic sandstone rock formations that rise majestically from the desert floor. With some towering 1,000 feet from the desert floor, they create a truly magical desert landscape. Be sure to stay up late at night to experience the Milky Way here and rise early to watch the sunrise over the valley, both of these experiences will stay with you for life. Ask about our special Star Gazing rooms and Navajo Tours through the Valley.

Day 15 : Winslow, Arizona

Distance: 199 miles

Today it's time to head back to Route 66 and the town of Winslow, Arizona. Your drive will take you through the stark landscape of the Hopi Indian Reservation. En route you may wish to stop just outside of Tuba City to view the Tuba City Dinosaur Track Site.The tracks were formed in the early Jurassic period, about 200 million years ago.

Since its beginning, Arizona's stretch of Historic Route 66 has been more than a road. The hearts of its people have inspired writers, film makers, photographers and artists. It's a stretch of Route 66 that represents classic cars, cowboys, diners and ever changing wonders from towering red cliffs, open spaces and endless blue skies. Your base for the next night is Winslow, made famous in the Eagles Hit, Take It Easy. Here you can actually stand on the corner AND see the girl in the flatbed ford. Winslow also serves as a base to explore other Arizona Route 66 attractions like the Wig Wam Motel and Navajo Museum at Holbrook, Joseph City and the Petrified Forest and Painted Desert.

Day 16 : Grand Canyon, Arizona

Distance: 144 miles

Rise early today as you've got a couple of fabulous sights to see. En route to Grand Canyon be sure to make time for a stop at fascinating Meteor Crater, the meteorite that carved this crater was believed to be 50 metres wide and to weigh over 300,000 tons when it came crashing down to earth over 50,000 years ago.

Next stop is the Granddaddy of all National Parks - The mighty Grand Canyon. Bon Voyage can ensure that you make the most out of your short time here by pre-booking helicopter trips over the North Rim, hiking or Jeep tours. 

Days 17 - 18 : Needles, California or Las Vegas, Nevada

Distance: 266 miles

Leave the Grand Canyon behind and continue your Route 66 holiday through Arizona stopping at quirky Seligman for breakfast at the Snow Cap Drive-In. Another must-do stop in Arizona is Kingman, head for downtown and the historic walking tour, followed by a visit to the Powerhouse Route 66 Museum and a bite to eat in one of the many Route 66 Diners here.

We figured that you may want some rest and relaxation, so your next stop for two nights is the laid-back Pirates Cove Resort on the banks of the Colorado River, near Needles, California. Here you'll stay in water view cabins with spacious patios.  Spend your time at the resort enjoying activities such as boating, fishing, kayaking and jet-skiing on the Colorado river, hiking the many trails, sunbathing or exploring California's section of historic Route 66. (recommended to visit late April - mid September).

Alternatively - If you'd prefer Las Vegas is also an option for your Route 66 holiday at this part of your journey. Spend a couple of nights in one of the 5 star swanky hotels that line the Vegas Strip. Take in a show, spend time designer shopping and dine in fabulous restaurants. Las Vegas has to be seen to be believed.

Days 19 - 20 : Santa Monica, California

Distance: 283 miles

Historic Barstow and the fascinating Route 66 Museum is a worthy stop today on your journey through the Mojave desert to the Pacific Ocean. Don't forget to drop into the wonderfully kitsch Peggy Sue's Diner, just 15 minutes from Barstow. This 1950's diner a firm favourite with all our Route 66 travellers.  

Your Route 66 adventure ends today at the famous Santa Monica Pier. This lively beach city is the oldest and biggest of LA's resort areas, perched on palm-shaded bluffs above the blue Pacific Ocean. There are miles of prepared paths for walking, jogging, cycling and skating. Hire bikes here and explore adjoining Venice and famous Muscle Beach; book a surfing lesson, relax on the beach and enjoy celeb spotting; or stroll around the beach stalls selling funky wares. Be sure not to miss Santa Monica's Third Street Promenade, for three blocks of shopping, dining and lively street musicians.

Day 21 : Fly Home From Los Angeles

As they say, all good things must come to an end and it's time for your early evening flight back to the UK.

Unless, of course, you are not quite ready to go home. Maybe you would like to extend your stay a few more days and continue north up the California coast to San Francisco and along one of the world's most scenic drives- Highway 1, the Pacific Coast Highway. Perhaps you may decide to leave the road behind and fly over to the Hawaiian Islands for some relaxation before heading back to the UK.

Call the USA travel specialists at Bon Voyage to discuss your perfect Route 66 Extended Road Trip.