Convertible on '66
Route 66 road trip holiday including the Grand Canyon and Las Vegas
Cruise America’s most iconic highway in true road-trip style with our 14-night Convertible on Route 66 adventure — a journey where the top stays down, the sky feels endless, and the open road becomes pure freedom. Beginning on the sun-drenched shores of Santa Monica, this trip blends vintage Americana with epic scenery as you cross deserts, forested mountains, neon towns and rolling Midwestern plains. From Las Vegas’ bright lights to the awe-inspiring Grand Canyon sunrise, and from the surreal landscapes of the Petrified Forest to the neon-striped streets of Tucumcari, the Mother Road reveals its magic mile after legendary mile.
As you glide east toward Chicago, each stop adds a new chapter: the cowboy spirit of Amarillo, Oklahoma City’s lively Bricktown, quirky roadside icons like the Blue Whale and Cadillac Ranch, and historic small towns in Missouri and Illinois where Route 66 nostalgia lives on. The journey builds to a triumphant finish in the Windy City, where world-class architecture, deep-dish pizza and Lake Michigan views await. Designed for travellers who want the true Route 66 dream — freedom, fun, history, and wide-open horizons — this is the ultimate way to experience America’s greatest road trip.
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!
14 night self drive holiday from £2,399pp including flights, accommodation & car rental
Highlights
Drive the legendary Mother Road in a convertible, from Santa Monica’s beaches to Chicago’s skyline.
Witness sunrise over the Grand Canyon South Rim — one of the world’s greatest natural wonders.
Explore neon-lit towns like Tucumcari, historic Wild West streets in Williams, and artsy Santa Fe or Albuquerque.
Finish with two unforgettable nights in Chicago, home to world-class museums, music and deep-dish pizza.
Your itinerary
DAYs 1-2: discover SANTA MONICA & LOS ANGELES
Golden beaches, Hollywood icons, and the official start of your Route 66 journey
Arrive at LAX, collect your rental car, and cruise into sun-kissed Santa Monica — the western terminus of Route 66. With two nights here, you’ll have time to unwind by the ocean, stroll the historic pier, and enjoy Pacific sunsets along Ocean Avenue. Spend your full day exploring Los Angeles highlights: the Walk of Fame, Beverly Hills, Rodeo Drive, Venice Beach boardwalk, and the famous Hollywood Sign. This is the perfect, glamorous beginning before the epic road trip ahead.
2 Nights in
Santa Monica, CA
Arrive &
Explore
Days 3–4: Santa Monica - Las Vegas
Desert highways, Mojave panoramas, and the neon magic of Las Vegas
Begin your Mother Road adventure with a drive through San Bernardino, passing the iconic Wigwam Motel, before stopping in Barstow for its excellent Route 66 museum. Continue across the dramatic Mojave Desert — long, open stretches perfect for top-down driving — until the shimmering skyline of Las Vegas appears on the horizon. Enjoy two nights in Sin City, where you can explore themed resorts, dazzling shows, and world-class dining, or take a scenic convertible cruise to Red Rock Canyon’s fiery sandstone cliffs.
2 Nights in
Las Vegas, NV
270 miles
Day 5: Las Vegas - Williams (for the Grand Canyon)
Hoover Dam marvels and classic Arizona Route 66
Depart Las Vegas and pause at the mighty Hoover Dam, one of America’s most impressive feats of engineering. Rejoin Route 66 in Kingman and continue through Arizona’s desert landscapes toward Williams, a historic Wild West-style town known as the Gateway to the Grand Canyon. With its vintage neon, saloons, and the Grand Canyon Railway, Williams is an atmospheric overnight base before tomorrow’s sunrise spectacle at the South Rim.
1 Night in
Williams, AZ
275 miles
Day 6: Williams - Holbrook
Grand Canyon sunrise, Route 66 legends, and the nostalgic charm of Holbrook
Rise early for a bucket-list sunrise overlooking the Grand Canyon South Rim — a moment of pure wonder. Afterwards, head east past Flagstaff’s pine forests and stop at the iconic Jack Rabbit Trading Post, home of the famous “Here It Is” billboard. Continue to Holbrook, a true Route 66 gem lined with neon-lit diners, retro motels, and Wild West ambience. This is classic Mother Road Americana at its finest.
1 Night in
Holbrook, AZ
145 miles
Day 7: Holbrook - Santa Fe or Albuquerque
Petrified Forest wonders, Painted Desert vistas, and the culture of New Mexico
Start the day exploring Petrified Forest National Park and the vibrant landscapes of the Painted Desert, where multi-coloured badlands and fossilised trees tell a 200-million-year story. Cross into New Mexico and choose your route: follow the original 1926 alignment into artsy, adobe-built Santa Fe, or stay on the later Route 66 alignment into neon-bright Albuquerque, known for Old Town’s historic plaza and famous filming locations.
1 Night in Santa Fe
or Albuquerque, NM
265 miles
Day 8: Amarillo, Texas
Tucumcari neon, the Route 66 Midpoint, and Cadillac Ranch at sunset
Rejoin the main Route 66 alignment and continue into Tucumcari, a beloved Mother Road town filled with glowing neon signs and vintage motor courts. From here the plains open out toward Texas, leading you to Adrian, the official Midpoint of Route 66. Arrive in Amarillo where you’ll visit the iconic Cadillac Ranch — a row of graffiti-covered cars half-buried in the desert — and enjoy hearty Texan hospitality.
1 Night in
Amarillo, TX
290 miles
Day 9: Amarillo - Oklahoma City
Art-deco landmarks, Route 66 museums, and lively Bricktown nights
Journey across the Texas Panhandle, stopping in Shamrock to admire the stunning art-deco U-Drop Inn. Continue to the Oklahoma Route 66 Museum in Clinton for a timeline of the road’s golden age. Pass by Lucille’s historic service station in Hydro before rolling into Oklahoma City, home to the vibrant Bricktown district — perfect for dining, nightlife, and live music.
1 Night in
Oklahoma City, OK
260 miles
Day 10: Oklahoma City - Springfield, Missouri
Blue Whale, Kansas charm, and the birthplace of Route 66
Today is filled with icons. See the adorable Blue Whale of Catoosa, drive the narrow nine-foot-wide Sidewalk Highway, and enjoy the 13-mile stretch of Route 66 through Kansas, complete with small-town charm in Galena and Riverton. In Missouri, arrive in Springfield, MO, celebrated as the official birthplace of Route 66 in 1926.
1 Night in
Springfield, MO
295 miles
Day 11: Springfield, MO - St Louis
Ozark hills, mural towns, and the iconic Gateway Arch
Drive through the forested Ozark Mountains, stopping in Cuba, known for its colourful Route 66 murals. Continue past Devil’s Elbow and other nostalgic roadside relics before reaching St Louis. Here, the gleaming Gateway Arch rises 630 feet above the Mississippi River — an unforgettable welcome to one of America’s great cities.
1 Night at
St Louis, MO
215 miles
Day 12: St Louis - Springfield, Illinois
Original brick Route 66 and Abraham Lincoln heritage
Cross the Mississippi back into Illinois and drive a rare preserved stretch of original brick Route 66 in Auburn. Continue through small Midwestern towns before arriving in Springfield, IL, home to the legacy of Abraham Lincoln. Visit his preserved home, the Old State Capitol, and Oak Ridge Cemetery.
1 Night in
Springfield, IL
100 miles
Days 13–14: Springfield, IL - Chicago
Final miles into Chicago and a big-city finale before departure
Complete your Mother Road journey with the final drive north toward Chicago. Stop in Pontiac for colourful murals and the excellent Route 66 Hall of Fame Museum, then continue through Bloomington, Joliet and into Chicago — the eastern terminus of Route 66. Spend two nights exploring this world-class city: visit Millennium Park’s Cloud Gate, take in sky-high views from the Willis Tower Skydeck, stroll the Riverwalk, and enjoy world-famous deep-dish pizza. On your final morning, enjoy a relaxed breakfast before returning your convertible and heading to the airport for your overnight flight home.
2 Nights in
Chicago, IL
200 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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