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A holiday on Route 66

The ultimate American road trip

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21 August 2017 by Simon Langley

Chartering nearly 4,000 kilometres across America, Route 66 is perhaps the world’s most iconic road trip, sweeping through verdant plains and arid deserts to link Chicago in the east and Los Angeles in the west. It’s a trip steeped in America’s birth story, the route taken by thousands seeking to escape the Great Depression of the early 20th century. And, to point you between the rich heritage of its great cities and railway towns, we’ve put together the following collection of highlights, moving from east to west – the direction of those original jalopies. It’s all showcased on our curated itinerary


Chicago is one of America’s great cities. And, it’s got the architecture to match, with glass-and-steel giants sentinel to such artistic whimsies as sculpture parks and open-air auditoriums that host some of the world’s finest classical concerts. It’s a similar story when it comes to the city’s second love – food. One moment you could be picking through the latest in molecular gastronomy, and the next tucking into that famous deep-dish pizza – best taken with a game between one of Chicago’s major league franchises. 

St. Louis

Found on the shores of the Mississippi, St. Louis is largest city in the Great Plains. It’s got the musical heritage to match, too, with the likes of Miles Davis and Chuck Berry having kick-started their careers in its foot-tapping bars – many of which are still open to this day. You can also sample those other great American pastimes – beer and baseball – at the city’s deified breweries and ball parks. Don’t’ forget to get that all-important snap at the top of the Gateway Arch – St. Louis’ 192m-tall steel icon. 


Tucked away in the Texas Panhandle, unassuming Amarillo marks a rough halfway point between Chicago and LA. For many, that’s been its only strength, but look closer and you’ll be treated to a glimpse into life in small-town America, complete with a big passion for steak. Indeed, the city is the self-styled ‘Beef Capital’, something best appreciated in its ranches and indulgent restaurants. It’s also home to one of Route 66’s icons – Cadillac Ranch. Here, a series of brightly painted, vintage Cadillacs are found upturned in the desert sands. 

Santa Fe

Evidenced by a superb collection of museums, Santa Fe is America’s oldest state capital. Indeed, you can trace its history back thousands of years, before its Native-American origins were superseded by Spanish colonialists in the 17th century. The work of these early settlers live on today in adobe neighbourhoods, the Romanesque St. Francis Cathedral and the city’s heart – the Plaza, a square packed full of European charm.

Petrified Forest National Park

The aptly named Petrified Forest covers over 200 square miles of Arizona badlands – a true wilderness right on the Route 66. Here, acres upon acres of fossilised wood dot a desert steppe making for immersive backcountry hikes. However, it’s perhaps the park’s stratified layers of rock that are the most impressive, tracing millennia of geological activity in spectacularly colourful bands.


Rolling into town to the twangs of a slide guitar, laid-back Flagstaff welcomes with microbreweries, historic architecture and a penchant for bluegrass. It’s all centred around a charmingly historic downtown, replete with turn-of-the-century residences and an imperious courthouse. Then, looking beyond the city limits, you’ll be treated to Flagstaff’s true obsession – the great outdoors. As your drive in will attest, there’s everything from skiing on desert-ringed peaks to hiking in America’s largest ponderosa pine forest.

The Grand Canyon

A true highlight of world travel, the Grand Canyon is rightfully at the top of many a bucket list. OK, it’s not on Route 66 itself, but as it’s barely an hour’s drive from the trail, this natural wonder – one of the hallowed seven – is more than worth the detour. You’ll be rewarded with sunset viewpoints, challenging hikes and even spectacular helicopter rides.

Las Vegas

Like the Grand Canyon before it, Las Vegas demands a short detour. This is American glitz at its most impressive, where the world’s icons are reimagined in brash neon, jetsetters pampered by ultra-luxury hotels and concert halls host a new headline act each and every night. But, while you’ll know it for its casino meccas, Las Vegas is also surrounded by some seriously stunning scenery, with mighty winds and tectonic machinations forming everything from vast canyons to high-altitude forests.

Los Angeles

Los Angeles, journey’s end, is the bright lights at the end of the highway. Of course, they’re most keenly felt with Hollywood’s glam – expressed by that sign and those boulevard stars – but there are also plenty of quieter charms to the City of Angels. We recommended heading to nearby Santa Monica where you’ll be treated to white sands, farmers’ markets and some of America’s finest dining, from humble taquerias to celebrity-chef indulgences.  

And finally, if you're hungry for more of America's great open roads, perhaps head north from Los Angeles along Route 1. Another of the USA's bucket-list journeys, this coast-hugging highway meanders past dramatic cliffs, sandy bays and sprawling vineyards all the way to San Francisco.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

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