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  • Route 66
  • Route 66
  • Route 66

Route 66 Holidays

Celebrated in song, cinema and folklore, Route 66 has come to signify the ultimate American road trip. It’s all about the freedom of the open road, the great outdoors and watching classic Americana pass by as the wind whips through your hair. Whether you want to embrace the elements, or save your hair-do and hire a car instead, we have the perfect Route 66 holiday for you.

Opened in 1926, Route 66 connected Chicago with the West Coast, along some 2,448 miles of asphalt. For much of its early life the road was the way of escape for thousands of migrants in their old jalopies escaping the Dust Bowl and hoping to find a new life in California. After World War II, it took wealthy holiday makers in their convertibles towards the Pacific Ocean and a new theme park called Disneyland.

Whilst much of the old highway has been supplanted by modern Interstates, many of the towns along the Mother Road have protected their Route 66 heritage. Motels, old gas stations and diners along the sidewalks have kept their neon signs and character and provide a glimpse of life as it was on the road in the '30's. There are also plenty of quirky roadside attractions which have achieved landmark status, like the Blue Whale at Catoosa and the Cadillac Ranch in Amarillo.

Back in Chicago, Lou Mitchell’s Café has been serving breakfast to travellers beginning their Route 66 journey since the road opened. So, whether you’re climbing in your car, riding a Harley Davidson or getting in the cab of your motorhome, why not stop for a coffee and eggs over-easy to start your trip in true American style.

Have a look at our suggested itineraries below or simply create your own unforgettable Route 66 road trip.

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The Windy City

This vibrant city at the Eastern end of Route 66 has the perfect combination of old and new. You can see the city’s sky high views atop its iconic skyscrapers, discover the great performing arts on offer and take a trip to the Navy Pier. Yet it's a city that's big on tradition too, and that includes a passionate allegiance not only to its major sports teams but to deep-dish pizza and its unique style of hot dog.

Route 66 Museum, Clinton Oklahoma

For the ultimate Route 66 experience, visit the Route 66 Museum in Clinton Oklahoma. Learn about the history of America’s most famous road; how it was built and how it evolved from a route of escape for victims of the Dust Bowl to a speedway for 1950s recreation and holidaymakers. The museum also offers changing special exhibits, focusing on the Route 66 experience.

Santa Fe

The oldest capital city in the United States combines distinctive Pueblo Revival architecture with an artistic soul and a dramatic mountain backdrop. Don’t miss a visit to America’s oldest public building, the Palace of the Governors in the Historic District. Or, for something different, buy a ticket for one of Santa Fe’s newest, the fantastic open-air opera house, opened in 1998.


For a taste of the old Wild West, the gold rush town of Oatman, Arizona is the place to park your horse, or more likely your car. Here you can watch regular gun fights (staged), feed wild burros (donkeys) and visit the hotel where Clarke Gable and Carol Lombard stayed on their honeymoon. This is also a town which is very proud of its Route 66 credentials and there’s plenty of memorabilia on show.

Santa Monica Pier

Above the landmark 1909 pier stretching out into the Pacific Ocean, you can read the sign that marks the “End of the Trail,” a direct reference to the end of Route 66. Here, amongst local surfers and crowds of international tourists, you can relax and enjoy everything from arcade games, amusement park rides like the famous Ferris wheel, and even a trapeze school.

Fly Drive Holiday: Historic Route 66

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

Take the iconic Route 66 drive from its starting point of Chicago, following its journey across the USA, stretching over 2,400 miles to its final point in Santa Monica. This legendary road needs to be driven at least once, whilst taking in a variety of pure Americana landscapes through some of the country’s biggest, oldest, most iconic and most peculiar sites along the way.
Click here for more details

Route 66 Guided Motorbike Tour

Chicago – Springfield – St Louis - Joplin – Oklahoma City – Amarillo – Santa Fe – Gallup – Grand Canyon – Kingman – Las Vegas – Victorville – Los Angeles

What better way to experience Route 66, one of the most famous highways in the world, than by motorbike? This exciting motorbike tour allows you to feel the wind in your hair as you ride 2,400 miles from Chicago to Santa Monica, crossing eight states and three time zones.
Click here for more details

You will need your ESTA!
The US authorities have imposed a requirement for passengers travelling under the Visa Waiver Programme (VWP), to register for Electronic Travel Authority if you are travelling to the US. Any passengers who have not made an application for and received their travel authorisation via ESTA before travelling may not be permitted to board the aircraft or could be denied admission at the US entry destination. But of course, neither possession of a visa, nor meeting the basic requirements for travelling visa-free on the VWP will guarantee a passenger admission to the United States. The final determination of admissibility is made by the immigration office at the port of entry.

Where can I apply for ESTA?
Prior to travel, you will need to visit and fill out an online application form.

When should I apply?
This will need to be applied for at least 72 hours prior to travel if you intend to travel to America.

How long is my ESTA valid for?
Your ESTA will be valid for up to two years, or until your passport expires. It is also possible for you to use for multiple entries to America. Just be sure to amend any necessary data, such as date of travel and your address whilst in the US.


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