Luxury Get your kicks on Route 66 vacations

Get your kicks on Route 66

The perfect 14 day road trip on Route 66 from Chicago to Los Angeles

Route 66, or also known as The Mother Road is one of the world’s most famous roads. It was one of the USA’s first highways and takes you from Chicago, Illinois right through to Santa Monica, California and passes through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona. It has now become the most popular route for the American Road-trippers out there.

We have devised the perfect 14-day itinerary, which allows you to see the best spots on this journey.

Day 1

Arrive in Chicago and collect your car hire. The start of this wonderful trip begins with 3 days and exploring this cool vibrant city.

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Out Of Office is a luxury tailor-made travel company with a focus on delivering exclusivity and inclusivity. Our passion for global adventure is matched only by our deep commitment to delivering exceptional five-star service.

Everything we do is customised and designed especially for you – our valued customer – based on your exact personal requirements. Each member of our team is widely travelled. This means you get access to first-rate travel insights and the best possible advice from our team of luxury travel experts.

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Days 2 – 3

Spend your days exploring the city, visit the top tourist spots and blend in with the locals and their cool laid back lifestyle.

Day 4

Pack up your car, making sure you have lots of water, snacks and a playlist filled with some classic cheesy songs. The historic route 66 awaits you, so get ready for the best two weeks of your life. Today you will be driving 205 miles to Springfield in Illinois. Here, you can visit Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home.

Day 5

Today your final destination will be St Louis, Missouri. If you get there early enough, then head to the Missouri Botanical Gardens, Citygarden or the iconic Gateway Arch. today you will have driven a total of 97 miles.

Day 6

On your way to Springfields, Missouri, make a stop at one of the most popular attractions on route 66, the Meramec Caverns. These incredible limestone caves are covered in stalagmites and stalactites. There are regular tours of the caves which last around an hour and ten minutes. After your tour, get back on the road until you reach Springfields, which is known as the birthplace of route 66 as it was here when officials named the Chicago-LA-highway ‘Route 66’. Today’s mile count is 216.

Day 7

On today’s itinerary, you will make your first stop in Tulsa, Oklahoma. Visit the Philbrook Museum which is home to a wide selection of art including exhibits from European, American, Asian, Native American and African artists. The museum is surrounded by acres of lush gardens, a perfect spot to have a picnic lunch. You will then end your day in Oklahoma City. Spend the evening exploring the local area.

Day 8

Texas is on the agenda today. You’ll make your night stop in Amarillo which is also famous for its selection of delicious steakhouses. Spend the evening in Amarillo and enjoy an evening meal in one of the many steakhouses. We recommend Big Texan Steak Ranch which is also the most famous.

Day 9

Today you will be heading to New Mexico. There are lots of interesting points to stop at along the way today including the Cadillac ranch, which is an art sculpture consisting of old Cadillacs which have been painted and represent the changing styles of the automobile. Stop at the Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. You’ll finish the day in air balloon obsessed Albuquerque.

Day 10

Today you will make a stop at the Meteor Crater which was created by an object hitting the ground at 12 miles per second, creating a shock force which was the equivalent of 12 Hiroshima bombs. It is pretty big to say the least… Detour to El Morro to see the signatures of past travellers carved into the rocks

Day 11

On route to Las Vegas stop at the incredible Grand Canyon. This vast rock hole is a truly breathtaking natural wonder. Today is the largest distance you will travel (365 miles) before you eventually end up in sin city!

Day 12

Spend the day exploring Las Vegas, hit the trip and test your luck in the casinos. If you wish, you can add another day in Vegas (in fact you can add as many days as you want in any of the stops!)

Day 13

The second to last stop on this road trip is Santa Monica and what a way to end a wonderful journey. Lounge on the white sandy ‘Baywatch beaches’. Instead of taking your car, hire a bike or a pair of roller blades and explore the city freely.

Day 14

Today you will be exploring Los Angeles. Immerse yourself in the glitz and glam and visit the Hollywood Boulevard and look for your favourite stars on the famous walkway. Cruise through Beverly Hills and goggle at the beautiful movie star mansions.

Your trip has sadly come to an end. Drop your hire car off at the designated store and catch your flight to your next destination, wherever that may be!

Enquire now and we can get planning on your USA road trip. We can tailor make anything to suit you

Primary Image: Dietmar Rabich

Why book with us?

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We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build the perfect trip for you.

Call our travel experts on +44 (0)20 7157 1570

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All the prices on our website do not include flights. We can, of course, arrange them for you.

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