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Historic Route 66

Historic Route 66 – Great American Road Trip

18-day tailor-made self-drive from £2,930 pp incl. flights


Short description

A road trip of epic proportions along America's famous Route 66


  • Experience the all-American road-trip tradition as you drive between Illinois and California
  • Encounter the Mid-West's vast landscapes and the ranch-studded plains of Texas
  • Look out to sweeping views of the Grand Canyon
  • Get a taste of American city living with stays in Chicago, St. Louis, Oklahoma and Las Vegas
  • End with the golden beaches of Santa Monica on California's Pacific coast

In Brief

  • 2 Nights Chicago
  • 1 Night Springfield Illinois
  • 1 Night St. Louis
  • 1 Night Springfield Missouri
  • 1 Night Oklahoma City
  • 1 Night Amarillo
  • 2 Nights Santa Fe
  • 1 Night Flagstaff
  • 2 Nights Grand Canyon National Park
  • 2 Nights Las Vegas
  • 2 Nights Santa Monica


Recommended for:
City | Desert | Self-drive

Built in 1926, what is known as the Main Street of America has transported millions of people in search of just about anything and everything. Almost 2,500 miles long, the road has served as an important route for decades, and 20 years ago, saw portions of it designated a National Scenic Byway, known as Historic Route 66. Beginning in Chicago, and taking in the best of the Midwest, you'll experience cowboy culture in Oklahoma, see the world wonder of the Grand Canyon and soak up the bright lights of Las Vegas before arriving into Santa Monica on California's sun-drenched Pacific coast.

Day by day itinerary

Days 1-2
Depart UK, Arrive Chicago

It's a long road ahead, so what better way to begin your Route 66 driving holiday than with included airport lounge access before your daytime flight to Chicago. Spend the next day exploring the city, perhaps discovering its vibrant art and music scene, internationally renowned for its soul, gospel, jazz and blues. There's some wonderfully eclectic dining to enjoy, too, from the 26 Michelin-starred restaurants to iconic hot dogs and deep-dish pizzas. Be sure to also take in the neon excitement of the Navy Pier and 'The Bean' in Millennium Park – a giant public art installation.

Stay: Hilton Garden Inn Central Loop (Superior)

Day 3
Springfield, Illinois

Pick up your hire car before heading onto Route 66. Your first stop will be Springfield, the state capital of Illinois. Once home to Abraham Lincoln, who lived and studied here during the mid-nineteenth century, Springfield is home to his presidential museum – also his home from 1837 to 1861 – while New Salem, a historic village, is just a short drive away. Our price includes an economy vehicle, but why not live the American muscle-car dream with an upgrade to a convertible Mustang, or similar? Ask our specialists for details.

Stay: President Abraham Lincoln (Superior)

Day 4
St. Louis, Missouri

Head on towards St Louis. If you're keen on baseball, beer and bowling, you’ll simply love this often-overlooked Mid-West city. Otherwise, you'll be instantly charmed by the famous Gateway Arch and a music scene that gave starts to the likes of Miles Davis and Chuck Berry.

Stay: Doubletree by Hilton Forest Park or similar (Superior)

Day 5
Springfield, Missouri

With its sweeping views and network of hiking trails, the Ozark Mountains – the world's second-oldest range – frame your approach to Springfield, Missouri, the town officially recognised as the birthplace of Route 66. Famed for its country music, Springfield's Ozark Jubilee was the USA's first country music TV show, featuring such stars as Johnny Cash and Patsy Cline as it drew an audience of more than nine million throughout its 1950s heyday.

Stay: DoubleTree by Hilton Springfield (Standard)

Meals: B

Day 6
Oklahoma City

Once a land of cowboys and Indians, the region around Oklahoma’s eponymous capital is one of endless dusty plains punctured by the occasional rocky outcrop. It's an evocative reminder of the old Wild West, which in turn is showcased in such cultural highlights as the city's National Cowboy & Western Heritage Museum and The American Indian Cultural Center.

Stay: Embassy Suites Oklahoma City Downtown (Standard)

Meals: B

Day 7
Amarillo, Texas

Moving out from central Oklahoma, there's the chance to explore the National Route 66 Museum, whose collection of classic cars and replica drive-in theatre are straight out of 1950s America. You'll then head east, crossing the border into the Texas Panhandle to arrive at Amarillo. Embrace the Lone Star State's big-is-best culinary ethos at the city's acclaimed steak restaurants and smoke houses before heading to the surreal Cadillac Ranch on the outskirts of town.

Stay: Holiday Inn Express Amarillo (Standard)

Days 8-9
Santa Fe, New Mexico

Drive on to Santa Fe, whose historic neighbourhoods set the scene for the country’s oldest annual fiesta. Designated as a UNESCO Creative City, Santa Fe has a vibrant arts, literature and music scene, with the likes of George R. R. Martin, D.H. Lawrence and Jack Schaefer all having lived here. Alternatively, if you prefer to get out into the countryside, the mountains surrounding the city host a vast network of hiking and biking trail. 

Stay: Best Western Inn of Santa Fe (Standard)

Day 10
Flagstaff, Arizona

Head towards Flagstaff, where high-altitude hiking, craft breweries and bluegrass-jamming buskers await. Small in size but rich in culture, Flagstaff's population of 70,000 celebrate a number of annual festivals and events, including the Flagstaff Festival of Science, Hopi and Navajo Festivals of Arts and Crafts and Arizona Highland Celtic Festival in the summer and autumn seasons. Music festivals such as Pickin' in the Pines and Flagstaff Friends of Traditional Music Festival showcase the best in bluegrass and folk, something the area is highly regarded for.

Stay: Little America Hotel (Superior)

Days 11-12
Grand Canyon National Park, Arizona

Make your way to the Grand Canyon – one of the world's seven natural wonders. Dating back around two billion years, the 277-mile long, 6,000 feet deep canyon is a World Heritage site that stays long in the memory. For the best views, and photos, its multi-coloured layers – which include some of the oldest exposed rock on the planet – drive the Desert View scenic route – a 25-mile jaunt along the Canyon's south rim. At sunset, the changing colours are truly spectacular. Of course, there's always the option of a helicopter flight.

Stay: Yavapai Lodge East (Superior)

Days 13-14
Las Vegas, Nevada

Big, bold, brash and unmistakably America, Las Vegas is an assault on the senses. You’ll have two action-packed days to enjoy all that ‘Sin City’ has to offer, trying your luck in some of the world's largest casinos, dining in some of America's best restaurants and taking in the biggest names in entertainment at its glitzy shows. It all provides a remarkable contrast to the tranquil, rugged beauty of the surrounding desert, which stretches out in all directions, as far as the eye can see. For your two-night stay in the city, we recommend an upgrade to the iconic Bellagio, whose dancing fountains pave the way for everything from classic car collections to art galleries and no fewer than three Michelin-starred restaurants. However, the most iconic experience remains a helicopter flight over the city lights.

Stay: Tropicana Las Vegas (Superior)

Days 15-16
Santa Monica, California

The final leg of your journey brings you right through the Californian desert to Santa Monica, just a short hop from Los Angeles Airport. Dropping off your hire car, you'll have three days to explore, with superb shopping, famers' markets and an iconic pier that's played a starring role in several Hollywood blockbusters. There's a diverse arts scene to discover, several acclaimed restaurants, from celebrity favourites to family-run taquerias, and a wonderful promenade which invites lazy evening strolls.

Stay: Gateway Hotel Santa Monica (Standard)

Days 17-18
Depart for UK

Enjoy a final morning in Santa Monica, before heading to Los Angeles for your overnight flight to the UK, arriving on day 18.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Standard Superior Deluxe

18-day tailor-made self-drive
from £2,930 pp incl. flights


Low Season

from £2,930 pp. incl. flights

High Season

from £3,840 pp. incl. flights


  • Complimentary UK airport lounge access
  • Return flights from London to Chicago and from Los Angeles to London
  • 14 nights accommodation in a mix of 3* (Standard) hotels and 4* (Superior) hotels on a room only basis 
  • 2 nights accommodation in a mix of 3* (Standard) hotels and 4* (Superior) hotels on a B&B basis 
  • 13 days Compact car hire (includes one way car hire fee)
  • Personalised self-drive information pack
  • All resort fees

Spoil yourself:

  • Please call us for a car hire upgrade to a Mustang Convertible or similar from an additional £175 per person

Route 66 by motorcycle:

  • Please enquire about out motorcycle hire options or guided motorcycle tours.

High season: June-September

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

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Every step of the way

Every step of the way

Our services are with you from start to finish:

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  • Free airport lounges on qualifying bookings
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