Route 66 + 1 (Highway 1)
An epic road trip holiday driving Route 66 from Chicago to Los Angeles, then California’s stunning Highway 1
Experience the ultimate American road trip on this extraordinary 20-night journey that combines the full length of Route 66 with California’s breathtaking Pacific Coast Highway. Begin in Chicago, where the Mother Road first came to life, and follow its storied path through small-town diners, neon-lit motels and classic Americana. Along the way you’ll discover vibrant cities such as St Louis, Oklahoma City and Amarillo, explore spectacular natural wonders including the Grand Canyon and Petrified Forest, and feel the timeless desert magic of New Mexico and Arizona. Two unforgettable nights in Las Vegas bring a burst of glittering energy before you roll triumphantly onto the Santa Monica Pier — the official “End of the Trail.”
From here, your adventure continues north along Highway 1, one of the world’s most spectacular coastal drives. Trace the curve of California’s golden shoreline through Santa Barbara’s Mediterranean charm, Solvang’s Danish-inspired streets and the rugged cliffs of Big Sur. Enjoy two nights in Monterey, where sea otters bob in kelp forests and the 17-Mile Drive offers endless ocean views, before finishing your journey in iconic San Francisco. With its perfect blend of history, culture, scenery and freedom, this holiday delivers the very best of the American road — a once-in-a-lifetime adventure from the heart of the Midwest to the Pacific Coast.
20 night self drive holiday from £2,999pp including flights, accommodation & car rental
Highlights
Cruise the legendary Route 66 from Chicago to Santa Monica, stopping at classic diners, neon motels and nostalgic roadside icons.
Visit the Grand Canyon, Petrified Forest and the Mojave Desert for spectacular Southwest scenery
Spend two nights in dazzling Las Vegas before reaching the Pacific at the famed Santa Monica Pier.
Drive the iconic Highway 1 through Big Sur, Monterey and Santa Barbara to vibrant San Francisco.
Your itinerary
DAYs 1-2: discover CHICAGO
Begin your adventure in the Windy City — the beginning of the Mother Road
Arrive in Chicago, collect your car and settle in for two nights in this bold, architectural city on Lake Michigan. Wander the bustling Magnificent Mile, admire world-class museums, and take in panoramic views from the Willis Tower Skydeck. Enjoy deep-dish pizza, explore Millennium Park’s famous “Bean,” or join a River Architecture Cruise that highlights why Chicago is considered America’s skyscraper capital. With its electric atmosphere and rich Route 66 heritage, Chicago is the perfect launch point for your epic journey.
2 Nights in
Chicago, IL
Arrive &
Explore
DAY 3: CHICAGO TO SPRINGFIELD, ILLINOIS
Historic Illinois towns, classic diners & Abraham Lincoln’s legacy
Your Route 66 adventure begins! Follow preserved segments of old 66 through small towns, neon-lit diners and vintage filling stations. Explore Springfield, Illinois’ capital and home of Abraham Lincoln, where you can tour his former residence and visit the solemn Lincoln Tomb at Oak Ridge Cemetery. For a real taste of the Mother Road, stop at the Shea’s Gas Station Museum or enjoy classic Americana at the Cozy Dog Drive-In — an original Route 66 icon.
1 Night in
Springfield, IL
200 miles
DAY 4: SPRINGFIELD TO ST. LOUIS, MISSOURI
Gateway Arch, brick-paved 66 & history along the Mississippi
Continue toward St Louis, stopping to drive a rare stretch of the original brick Route 66 in Auburn. In St Louis, stroll across the historic Chain of Rocks Bridge, once a major crossing over the Mississippi River, before admiring the shimmering Gateway Arch, symbolising America’s push westward. Explore vibrant neighbourhoods, blues music heritage, and the riverfront that helped shape the country’s expansion.
1 Night in
St Louis, MO
100 miles
DAY 5: ST. LOUIS TO SPRINGFIELD, MISSOURI
Birthplace of Route 66 & the rolling Ozark Mountains
Today’s drive takes you through the Ozark Mountains, a region filled with forested hills, limestone caverns and small-town Americana. Arrive in Springfield, Missouri, officially recognised as the birthplace of Route 66, where the highway was named in 1926. Visit the History Museum on the Square for interactive exhibits about the Mother Road, or explore local Route 66 diners and restored motels that keep the spirit of the 20th-century American road trip alive.
1 Night in
Springfield, MO
215 miles
DAY 6: SPRINGFIELD TO OKLAHOMA CITY
Three states in a day & the original 9-foot “Sidewalk Highway”
Ride through Missouri’s final miles, dip briefly into Kansas (just 13 historic miles of Route 66), and continue into Oklahoma, where some of the best-preserved stretches of old road remain. Drive the famous 9-foot-wide Sidewalk Highway, visit the Coleman Theatre in Miami, or stop at the Totem Pole Park for one of Route 66’s quirkiest attractions. End your day in Oklahoma City, home to the beautiful Bricktown district and the moving Oklahoma City National Memorial.
1 Night in
Oklahoma City, OK
285 miles
DAY 7: OKLAHOMA CITY TO AMARILLO, TEXAS
Cadillac Ranch, U-Drop Inn & wide-open Texas skies
Your journey continues through the great plains of the Texas Panhandle. Visit icons such as the U-Drop Inn in Shamrock — a stunning 1930s art-deco masterpiece — and the Route 66 Museum in Clinton. Just before Amarillo lies the legendary Cadillac Ranch, where brightly spray-painted Cadillacs rise nose-down from the desert. Don’t miss a classic steakhouse dinner tonight: Amarillo is famous for its Texas-sized hospitality.
1 Night in
Amarillo, TX
260 miles
DAY 8: SANTA FE OR ALBUQUERQUE
Drive Route 66 to Santa Fe or Albuquerque. Experience New Mexico culture, adobe architecture, and even Breaking Bad filming spots.
Follow Route 66 into New Mexico’s high desert, passing the ghost town of Glenrio and neon-soaked motels in Tucumcari. Continue to historic Santa Fe, famed for its Pueblo-style adobe buildings, rich Native American and Hispanic heritage, and world-class art scene. Wander the Santa Fe Plaza, explore museums along Canyon Road, or enjoy New Mexican cuisine infused with red and green chiles. Or Follow the later realignment through Albuquerque, home to the longest preserved urban stretch of Route 66. Cruise Central Avenue, lined with glowing neon, retro motor courts and classic diners. Visit Old Town, explore the Indian Pueblo Cultural Center, or ride the Sandia Peak Tramway for sweeping desert views.
1 Night in Santa Fe or
Albuquerque, NM
280 miles
DAY 9: HEAD TO HOLBROOK VIA PETRIFIED FOREST
Vibrant badlands & ancient fossilised trees
Rejoin the main route and continue west through New Mexico’s vintage 66 towns — Grants, Gallup and their mid-century motels — before entering Arizona. Explore the astonishing Petrified Forest National Park and the multicoloured layers of the Painted Desert, both rich in ancient geology, fossil beds and panoramic viewpoints. Spend the night in Holbrook, home to classic Route 66 wigwam motels and nostalgic roadside charm.
1 Night in
Holbrook, AZ
295 miles
DAY 10: HOLBROOK TO THE GRAND CANYON
Stand before one of the seven natural wonders of the world
Begin with quirky Route 66 classics like the Jack Rabbit Trading Post and the famous “Standin’ on the Corner” photo stop in Winslow. Continue into Grand Canyon National Park, staying just minutes from the South Rim. Witness an unforgettable sunset — or sunrise if you’re early — as the canyon shifts through gold, pink and deep crimson.
1 Night at
Grand Canyon, AZ
170 miles
DAYs 11-12: GRAND CANYON TO LAS VEGAS
Neon lights, shows & desert glamour
After a spectacular Grand Canyon sunrise, drive via the mighty Hoover Dam into Las Vegas for two nights of entertainment and relaxation. Explore the Strip’s iconic resorts, ride the High Roller observation wheel, visit the Neon Museum or enjoy world-class dining and nightlife. Prefer a quieter stop? We can easily adjust these days to suit your style.
2 Nights in
Las Vegas, NV
275 miles
DAYs 13-14: LAS VEGAS TO SANTA MONICA
End of the Road – Route 66 meets the Pacific Ocean
Cruise the final miles of Route 66 through the Mojave Desert into California, passing Barstow, Victorville and quirky roadside stops. Arrive at the Santa Monica Pier, the official “End of the Trail,” for a celebratory photo by the iconic sign. Spend two nights enjoying Los Angeles — from Griffith Observatory to Hollywood Boulevard, Venice Beach and more.
2 Nights in
Santa Monica, CA
270 miles
DAY 15: santa monica to SANTA BARBARA
Mediterranean charm on America’s Riviera
Head north as you begin your journey up the Pacific Coast Highway, passing palm-lined beaches, surf towns and oceanfront cliffs. Arrive in Santa Barbara, known for its Spanish-style architecture, wine-tasting rooms and relaxed coastal ambiance.
1 Night in
Santa Barbara, CA
85 miles
DAY 16: SANTA BARBARA to SOLVANG & CAMBRIA
Danish village charm & Hearst Castle grandeur
Stop in Solvang, a charming Danish-inspired village filled with windmills, bakeries and Scandinavian architecture. Continue toward Cambria, a peaceful coastal town framed by cypress trees and ocean vistas. Nearby Hearst Castle, the extravagant estate of publishing magnate William Randolph Hearst, offers incredible tours and sweeping Pacific views.
1 Night in
Cambria, CA
145 miles
DAYS 17–18: cambria to BIG SUR & MONTEREY
The world-famous Highway 1 coastline
Today is all about scenery. Drive the twisting, cliff-hugging road through Big Sur, one of the world’s most dramatic coastal routes. Cross the iconic Bixby Bridge, stop at McWay Falls, and admire panoramic views of rugged cliffs and turquoise coves. Spend two nights in Monterey, where you can visit Cannery Row, explore the world-class Monterey Bay Aquarium, or follow the 17-Mile Drive to Pebble Beach.
2 Nights in
Monterey, CA
105 miles
DAYS 19–20: monterey to SAN FRANCISCO
Cable cars, Golden Gate Bridge & your coastal finale
Take your final scenic drive into San Francisco, a city of cable cars, Victorian homes and sweeping bay views. Spend two nights exploring highlights such as Fisherman’s Wharf, Pier 39, Chinatown, Lombard Street, Alcatraz Island, and the magnificent Golden Gate Bridge. Wander through neighbourhoods like North Beach and Haight-Ashbury, ride a vintage cable car, or cycle the waterfront for spectacular views.
On your final morning, enjoy one last stroll through this iconic city before returning your car and heading to the airport for your overnight flight home — the perfect ending to a once-in-a-lifetime Route 66 + Highway 1 adventure.
2 Nights in
San Francisco, CA
120 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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