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Route 66 Explorer

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

The classic American Road Trip from Chicago to Santa Monica in Los Angeles. Itched into American folklore by those migrating west during the great depression. Our road trip is filled with nostalgia between some of the nations best cities.


Route 66 Explorer 14+ days

All of our American road trips can be tailored to meet your requirements. Do you have more or less than 14 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.

That's one big tick on my life list!


Home of the skyscraper

Day 1

Arrive in masculine Chicago

Arrive in Chicago and collect your wheels ready for this classic Route 66 road trip across America. You have three nights to really get to grips with this wonderful city on the beautiful Lake Michigan.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago's waterways

Day 2

Explore Chicago

Chicago is best explored by trolley, bus, boat or bike. Most visitors head to 'Magnificent Mile', a vibrant, bustling area home to upscale shops, 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 it’s beaches come alive in the spring, summer and fall.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago shoreline

Day 3

A third day to discover Chicago

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, make sure you spend at least one evening partying at Buddy Guy’s Legends.

  • Key location: Chicago, IL
  • Chicago, IL

Pontiac, IL

Day 4

Set off down Route 66

Start your engines, historic Route 66 awaits. The Illinois section is very well signposted, making it easy to enjoy highlights such as Route 66 obsessed Pontiac and historic Springfield. Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home are highly recommended.

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

Famous St Louis Arch

Day 5

Next up, St Louis

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 you have time be sure to try and catch a baseball game here at the Cardinal's stadium which is right in the heart of the city.

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

Meramec Caverns

Day 6

Visit the iconic Route 66 stop off - Meramec Caverns

Continue south today through the state of Missouri. On route stop off at Meramec Caverns, an extensive set of 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
  • 216 Miles

Philbrook Museum

Day 7

Tulsa and Oklahoma City today

Continue on the historic route you'll pass through Joplin, Missouri before skimming through a corner of the state of Kansas into Oklahoma and on to Tulsa. We recommend a visit here to the Philbrook Museum, home to a vast art collection, housed in an Italian style villa surrounded by a large idyllic garden. Continue onwards to Oklahoma City where you have a nights stay.

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

Cadillac Ranch

Day 8

Texas today

This morning we recommend a visit to the brick-town part of Oklahoma City for a filling morning meal where there are plenty of diners and restaurants. After breakfast try and fit in a visit to the moving Oklahoma City Bombing Memorial. Later you'll continue west to Texas to your stop for the night in Amarillo.

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


Day 9

Your 4th state in 5 days - New Mexico

On the way from Amarillo, you’ll have the chance to visit some classic 'Mother Road' attractions. This includes Cadillac Ranch, Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. New Mexico. You’ll finish the day in Albuquerque, New Mexico which still has a strong Native American and Hispanic community.

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

Meteor Crater

Day 10

El Morro, Petrified Forest National Park and Meteor Crater

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. You'll arrive tonight in Flagstaff for a one night stay.

  • Key location: Meteor Crater
  • Flagstaff, AZ
  • 324 Miles

Hello Grand Canyon!

Day 11

Las Vegas via the Hoover Dam & the Grand Canyon

90 minutes north of Flagstaff, is the Grand Canyon south rim. The worlds largest and most well known geological wonder is just staggering. Two billion years in the making, the Colorado River has forged a mile deep, 18 miles wide and 277-mile long gauge into Arizona. After exploring the trails, you’ll head northwest to the Hoover Dam before arriving in Las Vegas.

  • Key location: Grand Canyon NP
  • Las Vegas, NV
  • 356 Miles

Vegas Baby!!!

Day 12

Wake up to Vegas fun

Wake up in the luxury of Las Vegas. With so many first-class hotels, cuisine and entertainment to chose from you'll have plenty to keep you busy. Alternatively, spend the day relaxing by the pool or maybe have a flutter in the casinos.

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

Griffith Observatory

Day 13

Mojave Desert and LA glamour

Last stop Santa Monica! The pier signalling the final stop on classic Route 66. To celebrate your journey of nearly 2,500 miles, enjoy a meal overlooking the Pacific Ocean as the sun sets on California and your road trip adventure.

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

Route 66 - Done!

Day 14

Explore the city of Angels

Spend the day relaxing after your long journey or head out and sample 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 U.K.

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

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