Route 66 holidays

🇺🇸 Route 66 Holidays – Drive America’s Most Iconic Road 🇺🇸

Watch America unfold before your eyes as you journey along the legendary, ultimate American road trip with a Route 66 self drive holiday, experience a journey through the heart of the USA that’s as legendary as it is unforgettable. Spanning eight states and three time zones, this journey offers a front-row seat to America’s history, culture, and landscapes.

Route 66 takes you from the towering skyscrapers of Chicago to the sun kissed shores of Santa Monica, revealing the soul of America along the way.

Opened in 1926, Route 66 has inspired songs, films, and novels for generations.You’ve probably seen it featured on many television programs and films such as Disney/Pixar animation Cars, to Karl Pilkington’s An Idiot Abroad, and Billy Connelly’s Route 66.

Also an influence to may rock songs, Born To Be Wild (Steppenwolf), a cover by The Rolling Stones called (Get Your Kicks On) Route 66 and theme tune of the same name, to a popular TV Series, written and arranged by Nelson Riddle.

It was once a road of hope for those seeking a better life during the Great Depression, and later became the classic holiday route of the 1950s, bringing new life to small town America.

Although the original road was decommissioned, travellers can still follow most of its historic course, past retro diners, neon-lit motels, giant roadside attractions, and vast desert landscapes.

Every mile tells a story.

Why Choose a Route 66 Self Drive Holiday?

When you picture an American road trip, chances are you’re imagining Route 66. Known as the ‘Mother Road’, it’s the ultimate symbol of freedom and adventure. Driving Route 66 is like travelling through time, a nostalgic journey that captures the very essence of the American dream.

One of the good things about driving 66 is that most of the time when you are on the original route, there will be fewer other cars.

Along the way, you’ll pass through vibrant cities, small desert towns and scenic national parks, meeting friendly locals and discovering quirky roadside Americana. From classic car culture to historic diners and open road freedom, Route 66 offers a once-in-a-lifetime experience.

Where Does Route 66 Start and End?

Your Route 66 holiday usually begins in Chicago, Illinois, and winds its way west through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona, finishing in California at the famous Santa Monica Pier.

You can also drive the route in reverse ( from Los Angeles to Chicago ) often a cheaper alternative with the same unforgettable sights.

How Long Does It Take to Drive Route 66?

Route 66 stretches for about 2,448 miles (3,940 km) across the USA. To truly enjoy the experience, plan your itinerary carefully—allow at least 10–12 days, though we recommend setting aside around three weeks for your self-drive holiday. This gives you plenty of time to explore at your own pace.

Book accommodation and car rental in advance, especially if you want to stay in historic locations.

If you’re short on time, consider driving selected highlights of the route and flying between sections, using highways to connect the main stretches of the Mother Road.

What Car Should I Hire and How To Choose?

For a Route 66 trip, the best car to hire depends on your priorities.

A Classic American car experience, for the iconic Route 66, is a great choice to get into the spirit of the trip. Perhaps a Ford Mustang or Chevrolet Corvette.

Or a reliable, comfortable SUV or convertible for long distance comfort and open air views. Practical, with plenty of luggage space and comfort.

Where to Stay Along Route 66

Accommodation on Route 66 is part of the fun. In the larger cities, you’ll find stylish downtown hotels, while on the open road, you’ll stay in retro roadside motels, classic inns, and friendly local lodges, full of charm and character after a day of driving.

Highlights of a Route 66 Holiday

With so much to see and do, here are some of our favourite Route 66 highlights:

Chicago, Illinois – Snap a photo at the Route 66 Begin sign and explore this dynamic city’s skyline.
Pontiac, Illinois – Visit the Route 66 Hall of Fame Museum and explore vintage memorabilia.
St. Louis, Missouri – Ride to the top of the Gateway Arch for panoramic views of the Mississippi River.
Amarillo, Texas – See the famous Cadillac Ranch, a colourful art installation of half-buried cars.
Albuquerque, New Mexico – Enjoy the blend of Native American and Hispanic culture on this lively stretch.
Grand Canyon, Arizona – Take a helicopter flight over one of the world’s most breathtaking natural wonders.
Petrified Forest National Park, Arizona – Wander through a prehistoric landscape of fossilised trees.
Las Vegas, Nevada – Add a detour to experience a Cirque du Soleil show and the bright lights of the Strip.
Santa Monica, California – Celebrate at the ‘Route 66 – End of the Trail’ sign on Santa Monica Pier.

End your adventure with a few relaxing days in Redondo Beach, a quintessential Californian seaside town with golden sands, a lively pier, and a laid-back, coastal vibe. Explore the Riviera Village with its 300+ shops and restaurants, the perfect way to unwind after your epic journey.

Route 66: Things to Consider

Route 66’s fame can sometimes overshadow the practicalities of the drive. If you plan to cover the entire route, remember it’s a long journey with vast distances between stops.

We recommend a leisurely three week itinerary for the full experience. Short on time? You can always choose to explore individual sections and combine flights with shorter drives.

Outside major cities, expect simple but comfortable motels, part of Route 66’s authentic charm.

Plan Your Route 66 Adventure

Our experience of American travel can help create your ideal Route 66 self drive holiday fully tailored to your preferences. Simply tell us when, where, and how you’d like to travel, and we’ll take care of everything from car hire to accommodation and excursions that suit your requirements.

Best Time To Travel

The best time to drive Route 66 is between May and October, with September and October being particularly good months.

Get A Good Guide Book

A guide like the "EZ66 Guide" can be very helpful for navigating the old parts of the route.

The EZ66 Guide, created by Jerry McClanahan and the National Historic Route 66 Federation, provides turn by turn directions, maps, and travel tips for following the original Route 66.

It highlights attractions, history, and advice for driving east or west, making it the go-to guide for Route 66 travellers.