Itinerary

Land in the Windy City and transfer to your hotel. You’ll be staying at the historic Palmer House, an icon of downtown Chicago for over 150 years the hotel sits in the bustling theatre district right between the Art Institute of Chicago and Millenium Park. Get settled in and figure out what you have energy for after your flight.

Chicago has fantastic museums and galleries, including the best Impressionist collection outside Paris, and the Field Museum, home to SUE, the largest and most complete T-Rex ever discovered. If you’re planning to visit many attractions before heading out on the wide open road, then consider getting the Chicago CityPass which includes up to five attractions.

Before you head out on the road in two days’ time, make the most of Chicago by visiting some of its most iconic sites. Start your morning with a wander through Millennium Park to see the city’s most famous piece of public art, the Cloud Gate sculpture, known as The Bean. Afterwards, stroll the 18-mile Lakefront Trail for one of the best walks in the city, or take an architecture tour by boat to see some of the city’s magnificent skyline and major architectural landmarks. You’ll get to see the East Bank Club, the Willis (formerly Sears) Tower, the old Post Office Building, the John Hancock Center, the Wrigley Building and more.

Some would argue the city’s grandeur is best viewed from above. So instead of seeing Chicago by the lake or river, take a lift up to the highest observation deck in the USA, the Skydeck on the 103rd floor of the Willis Tower, or the 94th floor of the John Hancock Center for an alternative view from 360 Chicago.

In the evening, explore Chicago’s renowned food and drink – from Deep-Dish Pizza to an impressive international culinary scene and breweries to cocktail bars – you’ll find plenty to choose from along the Magnificent Mile and in the heart of the city.

Start your morning with breakfast at one of the stops on the historic Route 66: Lou Mitchell’s. Operating for over 100 years, this iconic Chicago restaurant serves up delicious diner fare, so you’ll be set up for a day of exploring.

Today is a day to catch up on any attractions or sights you might have missed in the city. There’s so much to see in Chicago, there’s bound to be a few things you’ll still want to see.

Come evening, enjoy Chicago’s nightlife, dominated by a rich musical heritage in both jazz and blues. From Buddy Guy’s Legends to Green Mill Jazz Club, a former Al Capone haunt – you can easily find some live music that plays to your tune.

Wake up early for the start of your Route 66 road trip to make the most of this first day. After collecting your rental car, drive over to the official “Begin” sign for Route 66 on East Adams Street, west of the intersection with South Michigan Avenue. Then, for commemorative photos and a bigger sign, complete with a coloured map, drive to the small, fenced park at Adams and Wabash Streets for one more “start” before heading off on your 479km 4.5 hour journey down to St. Louis.

Plenty of tourist attractions opened along Route 66 in the post-war boom era and visiting them on your road trip is part of the fun. From comical road signs and simple art installations to muffler men – giant fibreglass statues – there’s always something to see. First up is the Gemini Giant in Wilmington, Illinois. Originally placed here to advertise the local drive-in, this 30-foot statue was named after the Gemini space programme and gets you set for all the eccentricity to come.

Next, stop in Joliet. Part of the original 1926 alignment of the Route 66 in Illinois, it’s now on the National Register of Historic Places with the Route 66 Raceway and the stunning Rialto Square Theatre. A pit stop at the Route 66 Association Hall of Fame & Museum in Pontiac, Illinois, about 161km southwest of Chicago is also a must. While there, you’ll find Route 66 murals and other memorabilia, as well as the ever-popular Edinger’s Filling Station, a 50s-style diner should you feel hungry.

After another 318km filled with a host of famous motels, museums and drive-ins, you’ll be greeted by the 192-meter-tall Gateway Arch that looms above St. Louis and symbolises the city’s status as the gateway to the westward expansion of the United States. As St. Louis was once an important staging post for wagon trains heading west, it’s a suitable landmark to mark your own journey along Route 66. Take a trip to the top of this stainless steel “Gateway to the West” for breathtaking views of the city before checking in to your hotel, the beautiful, historic St. Louis Union Station. If you still have time, pass by the Anheuser-Busch Brewery, the City Museum or the National Blues Museum – all are great options for some late day exploring.

After a leisurely breakfast, head back out on the road for another 4 hour drive down to Springfield, Missouri. This 349km stretch of Route 66 takes you through the lush rolling hills of the Missouri Ozark Mountains, the second oldest mountains in the world, where you can stop for beautiful vistas and even a short walk or hike before you carry on. You’ll find the Meramec Caverns – signposted on countless billboards – in the Ozarks too. Straddling that fine line between geological marvel and tacky sideshow, the Caverns are home to rare cave formations that are colourfully illuminated to showcase their natural beauty.

Most of Route 66 to Springfield is now Interstate 44, but remnants of the old road can be found everywhere off the highway, so don’t hesitate to go off the main path just to explore.

When you do ultimately arrive in Springfield, you’ll be staying at one of the most iconic places to stay along Route 66, the Rail Haven Motel. Dating back to 1938 and filled with eye-catching Americana, this motel counts Elvis Presley amongst its guests and boasts classic cars, gas pumps and other original Route 66 items.

Downtown Springfield is a wonderful mix of eclectic shops, restaurants, antiques, museums and live theatres, so spend the day exploring all this city has to offer – you can even do a ride-through tour through another geological wonder, Fantastic Caverns.

If you need to stretch your legs after all the driving, a walk through the Nathanael Greene/Close Memorial Park or the Mizumoto Japanese Stroll Garden will be just the ticket. Aviary Café and Creperie comes highly recommended for lunch, and if you’re looking for somewhere to end the day, have a drink in one of the bars in Springfield’s Park Central Square. This is where the first recorded quick draw Wild West shoot out took place.

Start your journey over to Tulsa at your leisure. You’ll be cruising along the USA’s longest driveable stretch of the historic Route 66 covering 293km and around 3 hours on the road. This stretch lies parallel to the I-44. and features many eccentric stops along the way, like the world’s largest concrete totem pole in the folk art-filled Ed Galloway Totem Pole Park, or the Blue Whale of Catoosa that’s right out of the story of Jonah and the Whale.

As you arrive in Tulsa you’ll be greeted by murals, sculptures and neon signs that have beckoned to motorists for decades. Tulsa was once considered the “Oil Capital of the World” and played a major role as one of hubs of the American oil industry, but today it has both cosmopolitan and all-American appeal. You’ll see Art Deco architecture sitting alongside steel skyscrapers and rural Route 66 Americana next to modern museums. Pass by the Blue Dome district before or after heading to your hotel, the historic Ambassador. This neighbourhood, anchored by the 1920s-era Blue Dome gas station and situated on the historic Route, offers excellent dining and drinking options.

Tulsa bustles with vibrant neighbourhoods filled with art, culture and interesting things to do, so spend the day discovering whatever takes your fancy.

You can admire the facades of the early 20th century Philcade Building in downtown or head to the 1920s-built Philbrook Museum of Art. It not only has a world-class permanent collection, but also beautiful Italianate gardens to stroll through. For Western and Native American art, stop by the Gilcrease Museum.

Music lovers might be interested in either the Woody Guthrie or the Bob Dylan Centres, and for a general taste of life in this Midwest city, walk or drive through one of Tulsa’s charming neighbourhoods, like the Arts District, the Cherry Street District and the downtown Deco District. All have their own character and are well worth just setting out and exploring.

Get back on Route 66 for the 157km, 2-hour journey to Oklahoma City. The capital of Oklahoma, the city has nine fully preserved Route 66 landmarks all worth visiting, starting with the POPS 66 Soda Ranch just as you pass through Arcadia on your way in. As you drive into the city centre, you’ll pass through the Lake Overholser Bridge, see the iconic mid-century Tower Theatre and Will Rogers Theatre, the beautiful Gold Dome, the unmissable Milk Bottle Grocer and the State Capitol, which has an actual oil well on its grounds. Finish your round up of these historic sites with a meal at Cheever’s Café, the last stop on the city’s Route 66 landmarks.

Oklahoma City also has two excellent museums, the National Cowboy & Western Heritage Museum and the First Americans Museum, should you be interested in immersing yourself in the Wild West or Native American history of the state, before ending the day checking in to your overnight hotel.

Leave early again, if you can, to make your way to Amarillo. A midway point on the Mother Road that offers an inviting mix of Old West heritage and artistic energy, the drive there is 418km and roughly 4 hours. You’ll be weaving between Route 66 and the I-40 on your way there, stopping at two key points along the way: the National Route 66 & Transportation Museum, which is a standout among the many museums you’ll find along Route 66, and the Conoco Tower Gas Station & U-Drop Inn Café, a striking example of art deco architecture and the most stunning petrol station you will ever see.

You’ll then arrive in Amarillo’s phenomenal Route 66 historic district. Listed on the US National Register of Historic Places, it’s a 13-block development home to numerous buildings built in the Art Deco, Art Moderne and Spanish Revival styles, and serves as the hub for socialising in the town. Take your time to explore its many quirks before heading to Amarillo’s outskirts to see the famed Cadillac Ranch. This interactive installation features a sculpture of 10 classic Cadillacs half-buried in the ground, and lineups of classic cars from the 1930s to the 1970s with funky street art to match.

When it comes to finding your evening accommodation, you can’t miss it. The Big Texan is not only a fantastically fun western themed motel, but the adjacent Steak Ranch & Brewery is home to the biggest steak in Texas. And we guarantee a dinner there will go down in memory.

Depart after breakfast for the town of Tucumcari, a place that revels in its Route 66 connections with the historic highway running straight through the town centre. On your 180km or 1 hour 40 minute drive over, you’ll see remnants of a past now forgotten, like the San Jon Creek Bridge, the Old Bard Trading Post and the Historic Cedar Hill Grocery Store from the railroad era. But the real attractions are to be found when you arrive.

Tucumcari Boulevard, the town’s main street, is lined with Art Deco motel signs, original 1950s diners, and the funky Route 66 store, Teepee Curios, selling Route 66-themed souvenirs and memorabilia – make sure to get a photo in the storefront for your holiday album.

You’ll be staying the night at one of the town’s gems, The Blue Swallow Motel. Serving travellers along the Mother Road since 1939, it is a pleasant reminder of what it was like to travel across the USA in the good old days. And an evening spent under the neon lights in the historic courtyard can’t be beat.

Drive first thing to Santa Fe, one of the West’s oldest cities that embodies the relaxed lifestyle of the American Southwest. The journey is around 2.5 hours and covers 269km. Halfway through your drive you’ll come across the Route 66 Auto Museum – a mom-and-pop run museum with an amazing selection of classic, vintage, chrome and hot rod cars on display. For any automotive aficionado, this is a must-stop.

Afterwards, make the last push to Santa Fe. Known for its pueblo-style buildings, numerous galleries and superb museums., life here revolves around the central historic Santa Fe Plaza where you can sit, and people watch at a café. But there’s plenty to see if you want to go around and explore. You’ll be staying at the Hotel Santa Fe, the city’s only Native American-owned hotel that offers superb opportunities for relaxation as well as opportunities to tap into the local culture and cuisine influenced by the state’s Anglo, Hispanic, and Native American history.

Just an hour or so away from Santa Fe lies the sprawling high desert city of Albuquerque. Make the drive over this morning at your leisure – you’ll pass historic pueblos on your way. Albuquerque was founded in 1706 by the Spanish and boasts a well-preserved Old Town.

You’ll know once you’ve arrived in the city thanks to the many historic neon signs that light up the Old Route 66 running into town. The nostalgia is palpable yet charming, and you’ll be staying at another one of the Mother Road’s original motels, El Vado. Drop off your bags and head out to explore. Albuquerque is filled with great shops, restaurants and museums – head down Central Avenue to marvel at the vintage signs adorning the storefronts, and tuck into traditional diner food at the 66 Diner.

If you have time for some local culture, visit the New Mexico Museum of Natural History or the Indian Pueblo Cultural Centre, and catch some scenic views with a trip up the Sandia Peak Tramway.

The drive this morning from Albuquerque to Gallup is relatively short – 2 hours and 222km in total – so you can easily head over after breakfast. You’ll pass roadside ruins, old signs and abandoned gas stations along the way, and witness beautiful views across the high desert landscape.

When you arrive in Gallup you’ll be staying at the historic El Rancho Hotel. A famed stop on Route 66, El Rancho was a home for the movie stars who filmed Westerns in the area in the thirties and forties. Its significance also comes from the fact that countless Americans stayed here while travelling West along Route 66 in the hopes of a better life.

Gallup is situated in the heart of Native American ancestral homelands, and although it was once a headquarter for the southern transcontinental rail route, this present-day western town has developed into a unique destination: it is now a major trading post for more than 70% of the world’s Native American jewellery and art and is considered to be one of the USA’s last surviving trading posts.

Learn about the incredible artisanship that goes into making Native American art – and even buy a piece of two for yourself while you’re there – or immerse yourself in cultural events that happen every evening outside the Gallup Cultural Centre if you happen to be visiting during the summer.

The trip from Gallup to Holbrook might be short – just 154km and roughly an hour and a half on the road – but you’ll want to start early to spend a few hours at the only US national park found on Route 66: Petrified Forest National Park. Fascinating and awe-inspiring in equal measures, the park is renowned for its incredible Triassic fossils from the Mesozoic era and the surreal landscapes of the Painted Desert. Plan to spend 2 to 3 hours here, if not more, exploring.

Afterwards, you’ll drive just a short distance further to Holbrook, Arizona, home to one of the USA’s last remaining Wigwam Villages. Known for its quirky rock shops, giant dinosaur statues and classic diners serving the region’s signature Tex-Mex cuisine, Holbrook is also famed for its legendary motels, especially the one you’ll be staying at: the Wigwam Motel. You’ll be spending the night in a mid-century-built freestanding concrete tipi – one of 15 that make up the motel’s room selection and mistakenly referred to as wigwams – but fear not, as offbeat as they look, they are really good fun.

After breakfast, make your way over to Flagstaff at your leisure. The journey is just 148km and about 1.5 hours on the road. Just before you arrive in Flagstaff stop at Meteor Crater, the best-preserved meteorite impact site on earth – it’s a sight to see if you’re interested.

You’ll arrive in Flagstaff at the stylish Americana Motor Hotel. Sit back by the pool – it’s inviting – or head out to explore the local history which includes that of Route 66. Flagstaff is an inviting mix of Wild West charm with a lively yet laidback vibe, and the city offers an exceptional range of year-round outdoor activities.

The city’s historic district takes you right back to the Old West with its original architecture, and you’ll find plenty to do in the neighbourhood with a brewery trail, restaurants, art galleries, boutiques and self-guided walking tours like the “Walk This Talk” audio tour where you can learn about the original alignment of Route 66.

Flagstaff is just 128km from the South Rim of the Grand Canyon and just 45 minutes from the red-rock beauty of Sedona, so why not make a day of it in one of these stunning natural sites?

If you prefer to stay in Flagstaff, spend part of your day exploring Wupatki and Walnut Canyon National Monuments. From ancient cliff dwellings to stunning forest landscapes, there’s plenty to see. Come evening you can also go star-gazing at the world-renowned Lowell Observatory for one of the best views in the world of the night sky.

Leave on the early side to make the most of your next destination, Kingman. The journey is 235km and about 2 hours and 15 minutes. On your way over to Kingman from Flagstaff, take a stop in Seligman, where you’ll pass by the most bizarre-looing fast food joint you’ll ever see, Delgadillo’s Snow Cap. Built from scrap lumber back in 1953, this tiny shack defies perspective with its overcrowded interior, and makes a decent meal – especially if you left Flagstaff without having breakfast.

Continue on your way to Kingman – you’ll be staying just off the Historic Route 66 that passes right through the small city at the Best Western Plus A Wayfarer’s Inn. Drop off your bags and continue along the 66 further into town to see the official Historic Route 66 Downtown Sign before stopping into the Arizona Route 66 Museum, located inside Kingman’s Visitors Centre, which commemorates the historic road’s role in American history. Mr D’z Route 66 Diner is across the street should you be looking for somewhere for dinner later.

After your visit, stop into the Mohave Museum of History & Arts to trace local history or head to the Locomotive Park to see an original 1928 steam engine and visit the Kingman Railroad Museum to learn about the city’s past as a 20th century rail hub.

If you prefer to stretch your legs, put your walking shoes on and drive two minutes outside of Kingman to the Monolith Garden Trail for some spectacular desert scenery and moderately challenging hiking trails. No matter what you choose you’ll be in for a great afternoon.

Grab breakfast at your hotel before you head back out on the road – it’s good and chances are you’ll find options for everyone – and make sure to fill up on gas too for better prices. The drive over to Barstow is 330km and about 3 hours in total, and on your way there you’ll pass the dramatic terrain of the Mojave National Preserve, and a detour up to Calico, an old silver mining ghost town that offers a fun taste of the Old West, situated just before Barstow.

You’ll arrive in the small, lowkey town of Barstow at the Best Western Desert Villa Inn. Drop off your bags and head back out to explore. Barstow has the Route 66 Mother Road Museum which is filled with delightful Route 66 memorabilia, and the Western America Railroad Museum which preserves and shares the railroad history of the Pacific Southwest. You can even climb aboard an original locomotive.

Come nightfall check whether a film is showing at the local Skyline Drive-In Theatre. This original drive-in cinema still offers a one of a kind movie experience you aren’t likely to ever find again. If nothing is on head to Peggy Sue’s 50’s Diner for a solid meal and a quintessential 1950s dining experience.

Today you’ll be making your way to the very last stop on Route 66 right by the Pacific Ocean, Santa Monica. This last drive will be 210km and around 2.5 to 3 hours on the road with multiple interesting stops along the way.

First up is Elmer Long’s Bottle Tree Ranch in Oro Grande. A bewildering glass and metal forest made up of bottles collected by the late Elmer Long and his father by dump diving offers an enchanting beauty that is worth seeing for yourself.

Next is the town of Victorville, home to the California Route 66 Museum which offers interactive exhibits following the development of Route 66 from the time of early pioneer trails and railroads across over 420 square metres of gallery space. You may feel museum fatigue by this point, but this museum is still worth the trip.

Stop after in San Bernardino to see the Original McDonalds Museum. Whether you love it or hate it, there’s no denying McDonald’s impact on dining and pop culture, and this detour takes you back to its very beginnings with an array of memorabilia menus, toys and other McDonald’s artefacts.

You’ll then pass Rancho Cucamonga with its original Route 66 overpass and the historic 1915 gas and automobile service station, the Cucamonga Service Station which is still on an original segment of the Mother Road.

Keep driving until you just about reach the Pacific Ocean. Route 66 ends in the beautiful seaside town of Santa Monica at the intersection of Lincoln and Olympic Boulevards. You’ll see the official ‘End of the Trail’ sign and know that you’ve reached the literal end of the road. Find your hotel and relax – you’ve got a whole day to take it easy before you fly back.

Today is your day to live it up so why not make the most of your beachside location? LA’s laid-back neighbour, Santa Monica is quintessential California cool and teeming with opportunities for outdoor recreation. Catch some waves on no less than 5.6 kilometres of golden beach or sit back on the sand and soak up the sunshine. Jump on the solar-powered Ferris Wheel at the town’s historic pier or stand over the Pacific to watch the awe-inspiring nightly sunsets. Santa Monica has eight distinct neighbourhoods to explore, so you won’t run out of things to do. Stroll through the sculptures and rose gardens of Palisades Park, indulge in premium retail therapy at Third Street Promenade and peruse local markets and art galleries along Montana Avenue. You’ll be spoiled for choice come any mealtime too.

That said, if you want to still see some of the spectacular sights that Los Angeles has to offer, drive into the city just before or after rush hour in the morning and make a day of sightseeing.