Route 66 Holidays

Tours along Route 66

Few journeys on earth carry as much mythology as a drive along Route 66. Established in 1926, the aptly nicknamed 'Main Street of America' was the lifeline connecting rural communities to the booming cities of the west, carrying dreamers, Dust Bowl families and road-trippers through eight states – Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.

Travelling Route 66 today feels like stepping into a sepia-toned postcard that somehow still breathes. Small towns that time forgot line the route, each with their own quirky personality – and the ones that surprise you most are rarely the famous ones. Pull into Amarillo for a proper Texas-sized steak, or time your drive through Albuquerque for sunset, when the New Mexico sky ignites in coral and gold in a way that genuinely stops you in your tracks. In Arizona, the highway skirts the edge of the Painted Desert, where vast landscapes of purple, red and orange stretch endlessly to the horizon – pull over, because no photograph does it justice.

The beauty of a Route 66 road trip lies in its rhythm – there are no rigid itineraries here. Stop when something catches your eye, whether that's a vintage motel glowing in neon, a roadside diner where the pie is homemade and the coffee never stops flowing, or a stretch of original 1920s blacktop barely changed in a century. In our experience, the unplanned stops are almost always the best ones. Of course, there are numerous ways to experience the route – take it solo in a classic convertible, join a guided group tour, or weave Route 66 into a wider American multi-centre holiday combining cities like Chicago, Las Vegas or Los Angeles. However you choose to travel, this highway moulds to fit your sense of adventure, creating the kind of holiday you'll reminisce about for years to come.

Discover Route 66 icons

Route 66 is studded with landmarks so distinctive they've become symbols of American popular culture. No trip would be complete without encountering a few of these unforgettable icons along the way.

Begin at the official eastern terminus on East Adams Street in Chicago before heading south-west to the neon-soaked Gemini Giant in Wilmington, Illinois – a towering fibreglass spaceman that has been greeting road-trippers since 1965, and still raises a smile every time. Cross into Missouri to walk the cobbled riverfront streets of St. Louis and gaze up at the soaring Gateway Arch – ride the tram to the top if you can, because the view across the Mississippi is extraordinary.

Oklahoma offers the endearing Blue Whale of Catoosa, a hand-built roadside curiosity sitting serenely beside a pond and beloved by generations of passing travellers. Further west, the Cadillac Ranch outside Amarillo is one of America's most joyfully absurd art installations – ten Cadillacs buried nose-first in a Texas wheat field and spray-painted by visitors from around the world. Grab a can and add your mark; it's one of those experiences that sounds gimmicky until you're actually standing there. In Arizona, the town of Williams serves as a gateway to the Grand Canyon, while the eerily beautiful Petrified Forest National Park offers a glimpse of a landscape that has barely changed in millions of years. Finally, cruise into Santa Monica and dip your toes in the Pacific – you've earned it. The end of the road has never felt so rewarding.

Five reasons to journey Route 66

• Landscapes to leave you speechless – prairies, red rock canyons, desert and Pacific coastline all await.
• History at every turn – Native heritage, frontier towns and Route 66 museums bring America's story to life.
• A food lover's road trip – BBQ, green chile, Navajo fry bread and legendary roadside diner pie.
• Roadside attractions like nowhere else – from buried Cadillacs in Texas to a giant fibreglass spaceman in Illinois.
• Your trip, your way – drive it all, dip in and out, or combine with Las Vegas or LA.