Trailbreaker

“Get Your Kicks” - Route 66

***NEW TOUR***

The spirit of Route 66 is hard to pin down.  Isn’t it just a road? The answer is intangible as the Route means so much to so many

Bobby Troup’s immortal 1946 classic captured some of the essence when we were invited to "get hip to this timely tip. When you make that California trip". Steinbeck immortalised the highway by labelling it the ‘Mother Road’.  Perhaps it is more about America's Journey.  Its desire to seek adventure, new pathways and to pursue freedom.  And no one has a love affair with the automobile more so than the American motorist.

The Route will always be about discovery.  And people.  Stopping in the truck stops, cafes and legendary diners, sampling the coffee and the food and sharing a story with a waitress as the west ever beckons.

The cities and towns that dot the road shine like diamonds as they roll off the tongue. Tulsa, Amarillo, Albuquerque and Sante Fe.  They have a major place in our journey as do the tiny broken down towns left desolate by the super highway. 

But for us it is the spirit of the open road that takes us there.  We hope it will be a journey of discovery, as it is every time for us.

We drive, you enjoy!  However you are most welcome to hire some wheels and drive sections yourself...

Come on.  Come and get your kicks!

14 Day Itinerary
Departure:14th February 2026(Saturday to Friday)
Price:USD$2490          
Day 1 - Arrival day – Chicago
Arrival day. After our meeting we can enjoy dinner in one of Chicago’s famous downtown restaurants
Day 2 - Chicago to St Louis – (480km/300mil - 5 hours)
We head out today looking for the “Mother Road”. The original Route 66 has been whittled away in some parts but it is our intention to experience as much of the 'real' road as possible. We make a stop in Springfield, Illinois and take time to visit the Abraham Lincoln home and tomb, both National Historic Sites. On to St Louis in time to visit the famed Gateway Arch
Day 3 - St Louis to Branson – (410km/250mil - 4 hours)
Heading south west from St Louis we arrive in another Springfield, this time Missouri, which is where the road was named and thus recognised as the birthplace of Route 66. On to Branson for some wild ‘down home’ time. Branson is to country music as Las Vegas is to gambling. With over 50 dinner theatres and shows, this is the place to be, in ‘ol’ Missoura’. Be prepared to be country kitsched out!
Day 4 - Branson to Tulsa – (350km/220mil - 3.5 hours)
We head on to Joplin and visit Dale's Old Route 66 Barber Shop. A route 66 classic! Then to Tulsa once known as the "Oil Capital of the World". We have plenty of time to enjoy the city. High on the list is the Cherokee Heritage Centre where we can get a feel for Native American life the way it was before westerners arrived. Tulsa was also the birthplace of the legendary cowboy Will Rogers and we can visit his memorial and home
Day 5 - Tulsa to Clinton – (310km/190mil - 3 hours)
From Tulsa we have a short drive to Oklahoma City. Here we find the National Cowboy & Western Heritage Museum and stop to get a feel for the true “Wild West”. This museum reflects both Western and Native American art and artefacts as well as amazing photographs of the times gone by. Our final destination today is the town of Clinton, Oklahoma home to the “Route 66 Museum”. Another classic stop on 66
Day 6 - Clinton to Amarillo – (280km/175mil - 3 hours)
Our destination today is Amarillo in the great state of Texas! A must see is the bizarre Cadillac Ranch, an eccentric roadside legacy of the Route. We may choose to add our touch to the monument by spray painting the cars. Paint is even supplied! Amarillo has its own Historic Route 66 District which has theatres and shops offering a look into the old Route. A compulsory stop tonight is Big Texan Steak Ranch and Opry an icon of the fabled road. Renowned for the 72 ounce steak you will get it for free should you take less than an hour to dispatch. Good luck and remember everything is bigger in Texas!
Day 7 - Amarillo to Santa Fe – (450km/280mil - 4.5 hours)
We head in to New Mexico today en route to the oldest and highest state capital of Sante Fe. It is a detour from 66 but a worthwhile one. The city exhibits a blend of a history, cultural diversity and scenic beauty. There is an extraordinary variety of local arts and music reflecting the multitude of cultures present. Check out the Palace of the Governors and History Museum as it is the oldest public building in the USA. The Museum of Indian Arts and Culture is one of many centres devoted to the Native American presence in the long history of the region. Not surprisingly the food in Sante Fe is a highlight itself. The cuisine here is known for its influences from Pueblo, Mexican and western tastes
Day 8 - Santa Fe to Gallup – (320km/200mil - 3 hours)
Leaving Sante Fe we make a stop in the city of Albuquerque. The “66 Diner” is a must for lunch. The ‘sloppy Joe’s’ and milk shakes are not to be missed. Not much time for anything else in Albuquerque but remember not to “turn left” as they say. We are travelling through the open vistas of the west now and our destination is the small town of Gallup. The historic “El Rancho Hotel” built in 1937 has hosted a multitude of early Hollywood stars. Today the hotel still exudes character. We stay the night and get to play ‘Movie Star’ with no apologies necessary!
Day 9 - Gallup to Grand Canyon – (425km/265mil - 4.5 hours)
On the way today we enjoy many quick but interesting stops. Our first visit is to the Petrified Forest National Park before dropping into the Painted Desert Indian Centre. Next stop is Holbrook a hell fire frontier town of old where the infamous Pleasant Valley War was played out. A break in Flagstaff is next with time for a look in the quirky Museum Club to view its collection of stuffed animals. Finally we arrive at the Grand Canyon and are all set for a day of exploration
Day 10 - Grand Canyon
One of the world’s truly great sights. Technically not on Route 66 it is very close and a must see as part of our journey west. There are plenty of views and opportunities to gape from the rim. It is approximately 450 kilometres long and over 1 and a half deep. The Colorado River is responsible and still snakes through the canyon on its way to Mexico. We have time to hike on easy to moderate trails or enjoy a scenic flight over the canyon
Day 11 - Grand Canyon to Las Vegas – (440km/275mil - 4.5 hours)
Leaving the Grand Canyon we soon reach the longest uninterrupted section of the original Route 66 that is still in existence at 15 kilometres of straight road. This section runs between Ash Fork and Seligman. Our destination today is the bright lights of Las Vegas. We have earned a break and can savour the night lights and action of this enigmatic city dropped in the middle of the desert for the purpose of entertainment and frivolity. Count us in!
Day 12 - Las Vegas
'Vegas’ has something for everyone. Live shows, non stop casinos, theme parks and gregarious hotels. Check out Caesars Palace and the fountain show at the Bellagio Hotel. A drive down 'The Strip' in an open top car is a lifetime event. The idea is to recuperate for the last drive to the coast however the desire to taste all of Vegas may be far too strong
Day 13 - Las Vegas to Los Angeles – (430km/265mil - 4.5 hours)
A leisurely drive today making the most of our journey as we head towards the west coast. Roy's Café reminds us of why we travel this road. It is a Route 66 landmark reflecting times gone by on the open road. We head into the bustle of Los Angeles and our final destination, the pier at Santa Monica. Old Route 66 had its western terminus at the edge of the Pacific Ocean here and a brass plaque marks the official end of the Route. A toast to 'The Road' that affected so many and changed a nation. Did it change you?
Day 14 - Departure day - Los Angeles
Departure day

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