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Route 66 Ultimate Trip
Route 66 road trip holiday including the Grand Canyon, Monument Valley and helicopter tour over the Las Vegas Strip.
Experience America’s most storied highway on this immersive 20-night self-drive holiday along the full length of Route 66 — from the buzzing streets of Chicago to the palm-lined shores of Santa Monica. Travelling at a leisurely pace, this journey takes you across ten states and 2,400 miles of classic Americana, mixing neon-lit nostalgia with spectacular natural landscapes. You’ll explore charming small towns, stand at legendary roadside icons, and wander historic districts where the spirit of the Mother Road remains very much alive.
Along the way, you’ll venture into breathtaking national parks, including the Grand Canyon and the dramatic desert backdrop of Monument Valley. Discover vibrant cities like St Louis, Santa Fe, and Las Vegas, ride the famous Chain of Rocks Bridge, and stay in atmospheric Route 66 motels glowing with 1950s neon. Your adventure even includes a helicopter flight above the glittering Las Vegas Strip — the perfect high-flying contrast to the quiet, two-lane roads of America’s heartland. This is Route 66 at its most complete, authentic and unforgettable.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
20 night self drive holiday from £3,199pp including flights
Highlights
Drive the entire length of Route 66 from Chicago to Santa Monica at a relaxed, immersive pace.
Visit the Grand Canyon, Monument Valley, the Painted Desert and Petrified Forest National Park.
Explore Route 66 icons including Seligman, Hackberry, Winslow, Cadillac Ranch and Oatman.
Enjoy a spectacular helicopter flight above the Las Vegas Strip, included in your holiday.
Your itinerary
DAYs 1-3: ARRIVE and explore CHICAGO
Skyscrapers, deep-dish pizza and the official “Begin Route 66” sign
Fly into Chicago, drop your bags at your downtown hotel and dive straight into one of America’s greatest cities. Over three nights you’ll have time to stroll the Magnificent Mile, ride up to the Willis Tower Skydeck or 360 Chicago for jaw-dropping skyline views, and wander Millennium Park to see the mirrored Cloud Gate sculpture (“The Bean”). Explore Navy Pier, take a famous architecture river cruise, and discover world-class museums like the Art Institute or Field Museum. By night, sample legendary deep-dish pizza, blues and jazz clubs, and neighbourhoods such as River North or Wicker Park. Before you leave, don’t forget that all-important photo at the “Route 66 Begin” sign on Adams Street – the perfect send-off for your Mother Road adventure.
3 Nights in
Chicago, IL
Arrive &
Explore
DAY 4: SPRINGFIELD, IL
Classic Illinois 66, small-town diners and Abraham Lincoln history
Today your Route 66 journey truly begins as you leave Chicago and head south through Illinois farmland and small Midwestern towns. Stop in Wilmington to see the towering Gemini Giant Muffler Man, then call into Pontiac to admire colourful Route 66 murals and visit the excellent Route 66 Hall of Fame & Museum. Continue past classic gas stations, diners and courthouse squares to reach Springfield, the state capital and city most closely associated with Abraham Lincoln. Tour Lincoln’s Home National Historic Site, visit the moving Lincoln Tomb at Oak Ridge Cemetery, and stroll past the impressive State Capitol building. In the evening, enjoy a relaxed dinner in the historic downtown, soaking up the easygoing pace of an all-American Route 66 city.
1 Night in
Springfield, IL
200 miles
DAY 5: ST LOUIS, MO
Brick-paved 66, the Mississippi River and the soaring Gateway Arch
Leave Springfield and follow original sections of Route 66 through charming small towns like Auburn and Litchfield. In Auburn you can drive a preserved stretch of brick-paved Route 66, a tangible link to the highway’s early days. Continue south toward the Mississippi River and walk the historic Chain of Rocks Bridge, famous for its mid-river bend. Crossing into Missouri, you’ll arrive in St Louis, known as the “Gateway to the West”. Spend the afternoon at the impressive Gateway Arch National Park, where a tram ride to the top reveals sweeping views over the river and downtown skyline. In the evening, explore the city’s vibrant neighbourhoods, sampling St Louis-style barbecue, live blues music and riverside bars along the revitalised riverfront.
1 Night in
St Louis, MO
100 miles
Day 6: Springfield, MO
Ozark hills, neon nostalgia and the birthplace of Route 66
Today you’ll trade city skylines for the rolling hills and forests of the Ozark Mountains as you follow Route 66 southwest. Along the way, keep an eye out for classic motor court motels, roadside diners and vintage gas stations that capture the golden age of American road travel. You might pause in Cuba, Missouri – known as “Route 66 Mural City” – to admire colourful murals telling local stories. Your destination is Springfield, Missouri, officially recognised as the birthplace of Route 66, where the road was first designated in 1926. Visit local Route 66 exhibits or the Route 66 Car Museum, then wander the historic downtown filled with restored buildings, craft breweries and friendly restaurants. The mix of classic Americana and small-city charm makes Springfield a real Route 66 highlight.
1 Night in
Springfield, MO
215 miles
Day 7: Tulsa, Ok
Three states, classic icons and art-deco charm in Tulsa
Today’s ride is a true Route 66 classic as you travel through Missouri, Kansas and Oklahoma in a single day. After Joplin, you’ll briefly enter Kansas for just 13 treasured miles of the Mother Road, passing restored stops such as the Kan-O-Tex service station in Galena and the historic Rainbow Bridge near Riverton. Crossing into Oklahoma, don’t miss the photo-worthy Blue Whale of Catoosa, one of Route 66’s most beloved roadside icons. By late afternoon you’ll arrive in Tulsa, a city shaped by the oil boom and famous for its beautifully preserved art-deco architecture. Stroll the Deco District, check out live music venues and enjoy dinner in the lively Brady Arts or Blue Dome districts, where Route 66 history meets modern city energy.
1 Night in
Tulsa, OK
180 miles
Day 8: Oklahoma City, Ok
Sidewalk Highway, neon diners and the buzzing Bricktown district
This shorter drive lets you slow the pace and savour Oklahoma’s rich Route 66 heritage. Follow quiet backroads past rolling plains, stopping at vintage diners and motels that once welcomed Dust Bowl migrants and holidaymakers heading west. Make time to detour onto the legendary Sidewalk Highway between Miami and Afton, a narrow nine-foot-wide section of original Route 66 that feels like a ride back to the 1920s. Continue through small towns like Chandler and Stroud before reaching Oklahoma City, where modern attractions sit alongside historic neon signage. Spend your evening in the vibrant Bricktown entertainment district, filled with restaurants, canal-side bars, live music and sports venues – the perfect place to unwind after another memorable day on the Mother Road.
1 Night in
Oklahoma City, OK
115 miles
Day 9: Amarillo, TX
Panhandle plains, Route 66 museums and the legendary Cadillac Ranch
Today you’ll journey west out of Oklahoma into the wide-open spaces of the Texas Panhandle. Start with a visit to the excellent Oklahoma Route 66 Museum in Clinton, which brings the road’s history to life through classic cars, retro exhibits and 1950s music. Continue to Shamrock to see the beautifully restored art-deco U-Drop Inn, inspiration for Ramone’s body shop in Disney-Pixar’s Cars. Crossing into Texas, the landscape opens into big skies and endless horizons as you approach Amarillo. Just outside town, the iconic Cadillac Ranch awaits – a row of half-buried Cadillacs you can walk around, photograph and even spray with your own graffiti. In the evening, tuck into a hearty steak dinner and enjoy some authentic Texas hospitality in this true Panhandle city.
1 Night in
Amarillo, TX
260 miles
Day 10: Tucumcari, NM
Midpoint milestone, ghost-town ruins and neon-lit motels
Leaving Amarillo, your first major stop is Adrian, Texas, the official midpoint of Route 66, marked by a famous sign and classic café that celebrates travellers heading both east and west. It’s a great spot for coffee, pie and a celebratory photo. Soon after, cross the state line at Glenrio, a semi-abandoned ghost town where crumbling motels and gas stations show how the interstate bypass changed Route 66 forever. Continuing into New Mexico, you’ll arrive in Tucumcari, one of the best-preserved Route 66 towns, known for its vibrant murals and glowing neon signs. Spend the evening at a classic motor court motel and stroll along old Route 66, soaking up a 1950s atmosphere that feels frozen in time.
1 Night in
Tucumcari, NM
115 miles
Day 11: Santa Fe or Albuquerque, NM
Choose your route: historic Santa Fe or neon-lined Albuquerque 66
From Tucumcari, you have two historic alignments to choose from. Follow the original 1926 route north into the mountains to Santa Fe, where adobe architecture, centuries-old churches and a thriving art scene surround the historic Plaza; or take the later realignment to Albuquerque, where Route 66 became Central Avenue, lined with motels, diners and classic neon signage. In Santa Fe, browse galleries on Canyon Road, visit the Palace of the Governors and enjoy Southwest cuisine under clear desert skies. In Albuquerque, wander Old Town’s adobe courtyards, discover Route 66 landmarks like the KiMo Theatre, or hunt down filming locations from Breaking Bad. Either way, this is your chance to experience the unique blend of Native American, Hispanic and Western cultures that defines New Mexico.
1 Night in Santa Fe or
Albuquerque, NM
115 miles
Day 12: Gallup, NM
Rio Grande crossings, lava fields and a classic railroad Route 66 town
Today you’ll rejoin the main Route 66 alignment and head west through New Mexico’s big-sky landscapes. If you stayed in Santa Fe, you’ll drop down past rolling high desert to connect with Albuquerque; from there, continue along old 66 through towns like Laguna and Grants. Stop to explore the volcanic scenery and lava flows of El Malpais National Monument, or pause at roadside trading posts showcasing Native American jewellery and crafts. As you cross the Continental Divide, you leave the Rio Grande basin behind and roll downhill toward Gallup, long known as a film location for classic Westerns and a hub for Navajo and Zuni artisans. Spend the night in a historic Route 66-era hotel and soak up the atmosphere of this characterful railroad town.
1 Night in
Gallup, NM
115 miles
Day 13: Winslow, AZ
Petrified Forest wonders, Painted Desert vistas and “Standin’ on the Corner”
Cross the Arizona state line and enter a landscape rich in geological and cultural history. Your first major stop is Petrified Forest National Park, where ancient, fossilised logs lie scattered across badlands painted in shades of pink, purple and red. Drive the park road for sweeping views of the Painted Desert, stopping at viewpoints and short trails. Rejoining Route 66, continue toward Holbrook, where vintage neon and classic motels recall the Mother Road’s heyday. Your overnight stop is Winslow, immortalised by the Eagles’ song Take It Easy. At the Standin’ on the Corner Park, snap a photo with the mural and statue that pay tribute to the famous lyric, then explore the compact downtown with its historic buildings, galleries and cosy cafés.
1 Night in
Winslow, AZ
130 miles
Day 14: Grand Canyon, AZ
Flagstaff pines, South Rim viewpoints and a spectacular canyon sunset
Today you’ll leave the Route 66 corridor for one of the true natural wonders of the world. Drive through the mountain town of Flagstaff, surrounded by ponderosa pine forest, before turning north toward Grand Canyon National Park. As you approach the South Rim, the landscape opens into dramatic gorges and plateaus. Spend the afternoon exploring famous viewpoints such as Mather Point, Yavapai Point or Desert View, each offering a different angle on the canyon’s immense scale. You can walk a section of the Rim Trail, visit historic El Tovar Hotel and the Grand Canyon Village, or simply sit and watch the colours shift as the sun sinks lower. With your hotel just minutes from the rim, you’ll be perfectly placed to enjoy both sunset and, if you wish, sunrise the next morning.
1 Night at
Grand Canyon, AZ
140 miles
Day 15: Monument Valley, AZ
Sunrise over the canyon, Navajo Nation landscapes and cinematic desert scenery
Wake early to witness sunrise over the Grand Canyon, when the first light paints the cliffs in pinks and golds. After a leisurely breakfast, drive east along the rim road toward Cameron, enjoying more viewpoints before heading north through striking high-desert scenery into the Navajo Nation. As you near Monument Valley, the famous silhouettes of red sandstone buttes and mesas rise dramatically from the desert floor. This is one of the most recognisable landscapes in the American West, featured in countless films and adverts. Stay right by the valley for unbeatable views from your room, and consider joining a guided Navajo backcountry tour to learn more about the land’s cultural significance. As dusk falls, the silence and starlit skies make this a truly unforgettable stop on your Route 66 adventure.
1 Night at
Monument Valley, AZ
175 miles
Day 16: Williams, AZ
Scenic desert highways, historic Route 66 and a true Wild West town
Leaving Monument Valley, you’ll head south through dramatic red-rock scenery, passing the small town of Kayenta and skirting the edges of the Painted Desert once more. Rejoin the Route 66 corridor near Flagstaff and continue to Williams, a lively town proudly preserving its Mother Road heritage. Known as the “Gateway to the Grand Canyon,” Williams features a bustling Main Street lined with neon signs, classic diners, saloon-style bars and souvenir shops packed with Route 66 memorabilia. You might visit the depot of the Grand Canyon Railway, where vintage locomotives still depart for the South Rim, or catch an evening Wild West show on the street. With its mix of cowboy flair and roadside nostalgia, Williams offers one of the most atmospheric overnights on the route.
1 Night in
Williams, AZ
215 miles
Days 17–18: Las Vegas, NV
Desert detour to the bright lights, shows and helicopter views of the Strip
Today you’ll temporarily leave Route 66 for a two-night detour to dazzling Las Vegas. Drive west past Seligman, birthplace of the modern Route 66 preservation movement, and call into the wonderfully cluttered Hackberry General Store, crammed with vintage signs, pumps and classic cars. Continue via Kingman and the Mojave Desert before the neon glow of Las Vegas appears on the horizon. Over two nights you can stroll the Strip to admire themed resorts, fountains and world-class attractions, try your luck in the casinos or enjoy fine dining and live shows. A real highlight of your holiday is the included helicopter flight over the Strip, giving you a bird’s-eye view of the city’s dazzling lights as you fly past landmarks like the Bellagio, Caesars Palace and the Eiffel Tower replica. If you prefer, escape the bustle with a side trip to nearby Red Rock Canyon before diving back into the nightlife.
2 Nights in
Las Vegas, NV
220 miles
DAYs 19-20: santa monica - END OF THE TRAIL
Finish your epic Route 66 journey at the Pacific Ocean’s edge
Your final stretch leads you west across the vast Mojave Desert into California, passing classic Route 66 towns like Barstow — home to the Mother Road Museum — and Victorville with its excellent California Route 66 Museum. By afternoon, roll onto the world-famous Santa Monica Pier, where the iconic “End of the Trail” sign marks the triumphant finale of your Route 66 adventure. You’ll spend two nights soaking up the relaxed, coastal lifestyle of Santa Monica, with its beachfront cafés, oceanside cycle paths, and lively Third Street Promenade.
With Los Angeles on your doorstep, you can explore Hollywood Boulevard, enjoy stunning views from Griffith Observatory, or browse the boutiques of Beverly Hills. On your final morning, savour a last stroll along the sand or a relaxed breakfast by the ocean before driving to LAX to return your car and board your overnight flight back to the UK — the perfect close to an unforgettable, coast-to-coast American journey.
2 Nights in
Santa Monica, CA
270 miles
May- Jun & Sept- Oct: Weather is likely to be pleasant for the entire trip. The midwest shouldn’t be too cold and the southwestern states shouldn’t be too hot.
We would expect maximum temperatures to be in the 20°C - 30°C range in the midwest and 25°C - 35°C in the south and southwestern states
Flight times to/from Chicago is around 8 hours and Los Angeles is approx 11 hours. You’ll drive through 3 time zones. Chicago is 5 hours and Los Angeles is 8 hours behind the UK.
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