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Route 66 Explorer

Visit Chicago, Pontiac, Springfield, St Louis, Oklahoma City, Amarillo, Albuquerque, The Grand Canyon, Las Vegas & Los Angeles

This Route 66 holiday is an all-time classic road trip that’s been etched into American folklore by those migrating west along “The Mother Road” during the Great Depression of the 1930s.

Route 66 offers over 2000 miles of nostalgic Americana, ever-changing scenery and some of America’s best cities. Starting your road trip in Chicago, you’ll then cross through eight States as your drive to Route 66’s “End of the Trail” sign in sunny Santa Monica, Los Angeles.


Route 66 Explorer 15 nights

All of our Route 66 road trips can be tailored to meet your exact requirements. Do you have more or less than 15 days for your road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required. Just let us know when requesting your quote.

We loved every single mile of Route 66


Home of the Skyscraper

Day 1

Arrive in Chicago

You'll start your Route 66 road trip by spending 3 exciting days in Chicago. Many start by enjoying some famous Chicago Pizza or by going to the top of Willis Tower to watch the sunset and get the lay of the land. You'll be collecting your wheels on Day 4 to begin the drive down Route 66. For now, you'll be pounding the pavement from one outstanding attraction to another.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago's Waterways

Day 2

Discover The Windy City - Chicago

Chicago is best explored by trolley, bus, boat or bike. Most visitors head to 'Magnificent Mile', a vibrant, bustling shopping area home to upscale stores, trendy restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower and the 100-story John Hancock Center, which has a rooftop observation deck. Exceptionally cold in winter, the city and its beaches come alive in the spring, summer and fall.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago Shoreline

Day 3

A third day to explore Chicago's treats

Your personalised Road Trip Pack will detail all of Chicago’s must-see places, these include Cloud Gate, Navy Pier and the lovely Lake Michigan shoreline. Before leaving town for Route 66, make sure you spend at least one evening partying at Buddy Guy’s Legends.

  • Key location: Chicago, IL
  • Chicago, IL

Pontiac, IL

Day 4

Start your engines, historic Route 66 awaits today

Time to get your kicks on Route 66! The Illinois section of Route 66 is particularly well signposted, making it easy to enjoy highlights like Route 66 obsessed Pontiac and President Lincoln obsessed Springfield. Springfield's must-see places include Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and Lincoln's former home.

  • Key location: Springfield, IL
  • Springfield, IL
  • 200 Miles

St Louis Arch

Day 5

Next up... St Louis, Missouri

Arrive in St. Louis today which sits on the Mississippi River. Highlights include the Missouri Botanical Gardens, Citygarden and the iconic Gateway Arch National Park. If timing allows, be sure to catch a baseball game, the Cardinal's stadium is located right in the heart of the city.

  • Key location: St Louis, MO
  • St Louis, MO
  • 95 Miles

Meramec Caverns

Day 6

The iconic Route 66 stop off - Meramec Caverns

Continue south today through the State of Missouri. En route, you should stop off at Meramec Caverns, an extensive set of huge limestone caves offering memorable underground tours. You’ll end the day in Springfield, Missouri which is officially recognised as the birthplace of Route 66.

  • Key location: Meramec Caverns
  • Springfield, MO
  • 215 Miles

Tulsa's Philbrook Museum

Day 7

Onto Tulsa and Oklahoma City

Today Route 66 will pass through Joplin, Missouri before skimming through a tiny corner of the State of Kansas and on to Tulsa in the State of Oklahoma. Before leaving Tulsa, we highly recommend a visit to the Philbrook Museum, home to a vast art collection, housed in an Italian style villa surrounded by idyllic gardens. Afterwards, you'll continue on to Oklahoma City where you'll have a nights stay.

  • Key location: Tulsa, OK
  • Oklahoma City, OK
  • 285 Miles

Bricktown, OKC

Day 8

Your Route 66 holiday reaches Texas today

Industrial-chic Bricktown is a great place to enjoy a filling breakfast in one of the area's great diners. After breakfast, we recommend a visit to the moving Oklahoma City Bombing Memorial. Later in the day, you'll continue your Route 66 road trip west to find Texas and an overnight stop in Amarillo.

  • Key location: Amarillo, TX
  • Amarillo, TX
  • 260 Miles

Cadillac Ranch

Day 9

Your 6th State in 7 days - New Mexico

The first 170 miles of today's drive are packed with classic Route 66 attractions like Cadillac Ranch, The Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. You can then opt to finish the day with an overnight stop in either Albuquerque or Santa Fe. We'll talk you through pluses of both options when you request a quote from us. Santa Fe lies on the old or original Route 66 route and offers an upmarket spa town feel. Whilst Albuquerque lies on the newer, more direct route and is famous for the Sandia Peak Tramway and "Breaking Bad" filming locations.

  • Key location: Cadillac Ranch
  • Albuquerque, NM
  • 285 Miles

The Painted Desert

Day 10

El Morro, Pained Desert and Petrified Forest National Park

Included in your Road Trip Pack you'll find plenty of detailed suggestions about what to do and see on route. One of our favourites is the Meteor Crater near Winslow in Arizona. El Morro is a detour considering too to see 'inscription rock', a large sandstone pueblo where travellers since the 17th century have left messages. Later in the day, you'll pass through two Natural Wonders - Pained Desert and Petrified Forest National Park, before getting your head down in the classic Route 66 stop-off of Winslow, Arizona.

  • Key location: Petrified Forest NP
  • Winslow, AZ
  • 265 Miles

The Grandest Canyon

Day 11

The Grand Canyon is waiting to be ticked off your life list

Located one hour's drive north of Route 66 is the awe-inspiring Grand Canyon. The world's largest and most well known geological wonder is simply staggering. Two billion years in the making, the Colorado River has forged a mile deep, 18 mile wide and 277 mile long gauge into Arizona that will stay forever in the memory. Before leaving Route 66 however, you'll get the chance to experience another natural wonder in the form of Meteor Crater. Not as large a hole as the Grand Canyon, but in many ways just as spectacular and intriguing.

  • Key location: Grand Canyon NP
  • Grand Canyon NP
  • 135 Miles

Vegas Baby!!!

Day 12

Time for some Las Vegas luxury and fun

Again, it's not strictly on Route 66, but Las Vegas is so close that it would be rude not to pop by and say hello. Along the way, you'll pass by some iconic Mother Road locations like Seligman and Hackberry General Store. As you get closer to Vegas, you'll pass over the Hoover Dam before seeing the bright lights of Las Vegas in the distance.

  • Key location: Las Vegas, NV
  • Las Vegas, NV

Las Vegas Lights

Day 13

A second day of Las Vegas fun

With so many world-class casinos, restaurants, shops and entertainment options to choose from, you'll have plenty to keep you busy for two days. If that all sounds a little too rushed, then just spend your time relaxing by the pool in the Vegas heat. Want longer to enjoy Vegas? Then just let us know when you request a quote, we'd be more than happy to add additional days here or anywhere else on the road trip for that matter.

  • Key location: Las Vegas, NV
  • Las Vegas, NV

Route 66 - Done!

Day 14

Complete your Route 66 drive with a drive to LA

Cruise through the Mojave Desert to find Los Angeles, this will be your final stop on Route 66. To celebrate your completion of this iconic road trip, why not enjoy a meal overlooking the Pacific Ocean as the sun sets over the Pacific Ocean. You now have two or more days to pack in as much of LA's best bits as you can.

  • Key location: Los Angeles, CA
  • Los Angeles, CA
  • 285 Miles

Santa Monica Pier

Day 15

Explore the City of Angels

Spend the day relaxing by the pool after your Route 66 adventure or head out to explore the sites of Los Angeles. There's plenty to keep you busy. Hollywood is synonymous with glitz and glamour and is the most visited part of the city. Just a short drive northeast of here lies the Griffith Observatory, perched high on a hill overlooking the urban sprawl. This famous landmark is well worth a visit and great for views of the legendary Hollywood sign too. Tomorrow, you'll have the morning to continue exploring before flying home overnight to the UK.

  • Key location: Los Angeles, CA
  • Los Angeles, CA

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