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The Big Two

Chicago, St Louis, Oklahoma City, Grand Canyon NP, Vegas, Los Angeles, Santa Barbara, Monterey, San Francisco & more

The Big Two Road Trip. Route 66 and Highway 1 arguably the USA’s most famous routes. So if you are struggling to decide which one to do first, then why not go for this combo route! This itinerary chalks off both legendary drives in one epic 3 week adventure.


The Big Two 21 nights

All of our American road trips can be tailored to meet your requirements. Do you have more or less than 21 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.

Best road trip imaginable, It really was special !


The Chicago Shoreline

Day 1

Arrive in the masculine Chicago

After touching down at Chicago O'Hare, you'll jump in a cab and head downtown towards one of the world's greatest skylines. After settling into the hotel that we carefully selected for you, you'll have three nights and two full days to really get to grips with this wonderful city which sits on the shore of beautiful Lake Michigan. Should you want longer to explore Chicago, then just let us know when you call for a quote.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago River

Day 2

Explore Chicagoland

Most visitors to Chicago head straight to 'Magnificent Mile', a vibrant, bustling area which is 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 Hancock Center, which has a rooftop observation deck called 360 Chicago. Spend the rest of the day exploring some of the other attractions found north of the Chicago River. These include Navy Pier, Wrigley Field and the beaches found along the shoreline of Lake Michigan.

  • Key location: Chicago, IL
  • Chicago, IL

Cloud Gate

Day 3

A third day to discover Chicago

On your final full day in Chicago, we recommend that you spend time visiting the cities attractions that are located south of the Chicago River. Some of America's very best museums are found here, these include the Art Institute, the Alder Planetarium and the Field Museum of Natural History. Be sure to stroll around Millennium Park too, you'll find world famous outdoor artworks like Cloud Gate and Crown Fountain for those all important Social Media snaps. Lastly, before leaving town, make sure you spend at least one evening partying at Buddy Guy’s Legends Nightclub.

  • 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 really well signposted, making it super 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 Springfield attractions.

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

Gateway Arch

Day 5

Next up, St Louis - the gateway to the west

St. Louis sits on the banks of Mississippi River, and over the years the city played a pivitol role in the mass migration west, and thus it earned the nicknames - The Gateway City and Gateway to the West. Highlights include the Missouri Botanical Gardens, Citygarden and the iconic Gateway Arch National Park. Your personalised Road Trip Pack will tell you all the available options for this day and the rest of your fly-drive holiday.

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

Meramec Caverns

Day 6

Stop at Springfield

Continue south today through the State of Missouri. En route, we recommend that you stop off at the magnificent 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: Springfield MO
  • Springfield, MO
  • 216 Miles

Philbrook Museum

Day 7

3 States in one day - Hello, Missouri, Kansas and Oklahoma

Continue west along historic Route 66, you'll then pass through Joplin, Missouri before skimming through a corner of the State of Kansas and on to Tulsa, Oklahoma. Whilst in Tulsa, we highly recommend a visit to the Philbrook Museum, home to a vast art collection, housed in an Italian style villa surrounded by a large idyllic garden. Between Tulsa and OKC, we suggest that you fill up with gas and delicious soda at Pops which is an iconic stop located on Route 66 in the town of Acadia. Once you've arrived in Oklahoma City, visit the Bricktown District of the city for a bite to eat at one numerous diners and restaurants found here. Lastly, before leaving town, consider visiting the moving Oklahoma City National Memorial which remembers the victims and survivors of the 1995 Oklahoma City bombing.

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

Route 66

Day 8

Texas Today

Your Road Trip Pack will show you the way to Amarillo, it's found due west in the heart of the Texas Panhandle. You'll pass some awesome Route 66 museums along the way, which are packed with nostalgic Americana, classic cars and more. Once you hit Amarillo, there's only one place for any true road-tripper to go for dinner. The Big Texan Steak Ranch & Brewery is simply a must, just make sure you arrive hungry as the portions are HUGE.

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

Cadillac Ranch, TX

Day 9

Your 5th state in 9 days- Albuquerque

On the way out of Amarillo, you’ll have the chance to visit some classic 'Mother Road' attractions. These include 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. Highlights include the Sandia Peak Tramway, Old Town and Nob Hill.

  • Key location: Albuquerque, NM
  • Albuquerque, NM
  • 288 Miles

Meteor Crater

Day 10

Welcome to Winslow

Included in your Road Trip Pack you'll find plenty of detailed suggestions about what to do and see on each day of your holiday. El Morro is a detour well worth considering, you'll see 'Inscription Rock' which is a large sandstone pueblo where travellers since the 17th century have left messages. Another highlight of the day is The Painted Desert, which offers up multicoloured rock formations to amaze. After a busy day, you'll arrive in the classic Route 66 stopover town of Winslow for a one night stay.

  • Key location: Winslow, AZ
  • Winslow, AZ
  • 265 Miles

Epic Grand Canyon NP

Day 11

Meteor Crater and The Grand Canyon await today

One of our favourite Route 66 wonders is Meteor Crater , located near Winslow, Arizona. You'll then move onto Flagstaff for lunch, before driving 90 minutes north of Route 66 to find the south rim of the Grand Canyon. The worlds largest and most well known geological wonder, this is truly a staggering sight. Two billion years in the making, the Colorado River has forged a mile deep, 18 miles wide and 277-mile long gauge into Arizona. Stay and watch the sunset over the Canyon, before turning in for the night after another epic day of exploring.

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

Vegas Baby!!!!

Day 12

Next up - Las Vegas via the Hoover Dam

Watching the sunrise over the Grand Canyon will stay with you for life, after enjoying this spectacular sight you'll return to Route 66 and visit classic Mother Road small towns like Seligman and Hackberry, before cruising past the Hoover Dam on your way to the man-made wonder that is Las Vegas. After settling into your chosen Las Vegas hotel, why not get dressed up and hit the town for a night of partying and maybe even a little gambling.

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

Fountains at the Bellagio

Day 13

Waking up in Vegas

Wake up in the luxury of your Las Vegas hotel. With so many first-class cuisine, shopping and entertainment options to choose from, you'll have plenty to keep you busy today. Alternatively if you just want to relax, then why not just spend the day by the pool.

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

Route 66 - Done !

Day 14

Route 66 finish line awaits in Santa Monica

Today is the last stop on the Route 66 section of your holiday, the Santa Monica Pier signals the "End of Trail". To celebrate, we suggest you enjoy a rewarding meal at one of the Pier's many eateries which overlook the Pacific Ocean. Venice Beach lies just down the coast, why not rent a bike and cruise along the boardwalk between these two iconic LA beach towns.

  • Key location: Santa Monica, CA
  • Los Angeles, CA
  • 294 Miles

Beverly Hills

Day 15

A full day to explore LA

There's plenty to keep you busy in Los Angeles. 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. In between the coastline and the Hollywood area, lies Beverly Hills, The Getty Center and the transformed Downtown area. If you think you'll want to visit all these areas then you might want to request an extra day in LA when you call for a quote.

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

Santa Barbara

Day 16

Set off for the American Riviera

Time to explore the second iconic road of this holiday. Whether you call it the Pacific Coast Highway, Highway 1 or the Cabrillo Highway, you won't be disappointed by this 400 mile stretch of stunning road. Today, you'll leave Los Angeles and pass-by Malibu on your way north to Santa Barbara, this charming Mediterranean style town is one of the central coasts top highlights. Stroll along historic State Street, visit the Santa Barbara Botanic Gardens or simply enjoy the towns beautiful beaches.

  • Key location: Santa Barbara, CA
  • Santa Barbara, CA
  • 96 Miles

Classy Carmel Beach

Day 17

Explore Americas prettiest town

Today you'll make your way up to Carmel which is located at the southern end of Monterey Bay, along the way you'll experience the natural beauty of Big Sur and find out why people hold the Pacific Coast Highway so dear to their hearts. Carmel is a charming place which offers two world-class beaches backed by a small town made up of beautiful homes, quaint streets and fabulous restaurants. The wild and wonderful Point Lobos is just a couple of miles south of Carmel, this small State Park is truly beautiful and it can be enjoyed on short manageable hikes.

  • Key location: Big Sur, CA
  • Carmel, CA
  • 244 Miles

Whales in the Bay!

Day 18

Head to Cannery Row or enjoy Carmels finest beaches

In the morning, we suggest you cruise around the famous “17 Mile Drive” whilst on your way over to neighbouring Monterey. You’ll pass millionaire mansions, Pebble Beach Golf Club and stunningly beautiful rugged coastline. Monterey was once California’s capital but today it's best known for the world-class Monterey Bay Aquarium which is located on Cannery Row. Want to experience the Bay up close? Then we highly recommend you take a whale watching trip from Fisherman’s Wharf, Monterey is considered one of the best places in the world for this activity.

  • Key location: Monterey, CA
  • Carmel, CA

Golden Gate Bridge

Day 19

America's favourite city - San Francisco

The last leg of this epic road trip holiday awaits, take the short drive north to San Francisco, you'll pass through retro surf town Santa Cruz and also picturesque Pigeon Point Light Station along the way. In the evening, enjoy a meal in one of the city's excellent restaurants before settling in for the night. Get a good nights sleep tonight, you'll need your energy for the next two full days of exploring this wonderful city.

  • Key location: San Francisco, CA
  • San Francisco, CA
  • 123 Miles

'The Painted Ladies'

Day 20

So much to see and do in San Francisco

Once the fog lifts, one of America’s favourite cities will be revealed. Ride a cable car, climb the streets and get into the vibe that only this city can offer. San Francisco is full of Victorian charm, famous movie locations and wealthy tech companies, this city has it all.

  • Key location: San Francisco, CA
  • San Francisco, CA


Day 21

Another day in the Golden Gate City

Another day to explore San Fran’s must-see places which will be listed in your personalised Road Trip Pack. These points of interest include Coit Tower, Lombard Street, the Painted Ladies, Union Square, The Golden Gate Bridge, Fisherman's Wharf and Alcatraz to name just a few. Good luck cramming it all in, before you fly home the following afternoon.

  • Key location: San Francisco, CA
  • San Francisco, CA

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