Itinerary Highlights
- Follow the legendary Route 66 from Chicago to Santa Monica on the ultimate American road trip
- Stop at iconic Route 66 attractions such as the Route 66 Car Museum near Springfield + The National Cowboy & Western Heritage Museum
- The Oklahoma City Route 66 Museum in Clinton, and Elk City's Route 66 and Transportation Museum
- Cadillac Ranch features 10 graffiti-covered Cadillacs buried nose-first in the Texas soil
- Best time to travel April to October
What's Included
- Accommodation Throughout
- Car Hire
- International Flights
18 nights from £21,945 per person
Lucy
Travel Specialist
Set off on the ultimate Route 66 adventure from "City Lights to Canyon Heights," an 18-day journey from Chicago to Los Angeles, blending iconic Americana with breathtaking landscapes. ? Begin in Chicago, exploring its vibrant culture, stunning architecture, and world-class dining. ? Cruise through the nostalgic Route 66, stopping at landmarks like the Route 66 Hall of Fame Museum in Pontiac, Illinois, and the World's Largest Catsup Bottle in Collinsville, Missouri. ?
Experience the cowboy charm of Oklahoma City, the quirky Cadillac Ranch in Texas, and the serene beauty of Santa Fe, New Mexico, with private tours of its historic Plaza and Bandelier National Monument. Marvel at the Grand Canyon’s South Rim on a guided hike, and soak in the tranquility of Amangiri’s luxurious desert retreat near Lake Powell. ?
Continue to Sedona’s red rock formations for a guided hike, then journey to the dazzling lights of Las Vegas, stopping at roadside gems like the Seven Magic Mountains and Elmer’s Bottle Tree Ranch. Conclude your trip with an e-bike ride along the iconic beaches of Santa Monica and Venice Beach. ? This unforgettable road trip combines history, culture, and natural wonders, offering a once-in-a-lifetime experience along America’s legendary highway.
Itinerary
Day 1 Arrive in Chicago
Chicago, Illinois
Arrive in the ‘Windy City’ of Chicago, where a private transfer whisks you to your downtown hotel. Hotel: Pendry Chicago
Day 2 Chicago, Illinois
Discover Chicago’s architectural brilliance and cultural energy. Begin in Millennium Park, where the reflective curves of ‘The Bean’ capture the city’s skyline. Immerse yourself in world-class art at The Art Institute of Chicago, home to the famous Nighthawks by Edward Hopper and other timeless masterpieces. Then step aboard the First Lady River Cruise for a fascinating architectural tour from the water, as expert docents share insights into the city’s most striking landmarks.
Day 3 Chicago, Illinois to St Louis, Missouri (300 miles)
St. Louis, Missouri
Collect your rental vehicle for the start of your Route 66 adventure. Your next destination is — ‘The Gateway to the West’ — where you'll pick up your Route 66 wheels. Explore the city at your own pace, beginning with the Gateway Arch National Park, where a tram ride to the top offers sweeping views of the Mississippi River. Experience Forest Park’s cultural treasures, including the St Louis Art Museum and the Missouri History Museum, and stroll its botanical gardens. After a day of sightseeing, retreat to the Four Seasons Hotel St Louis for an exquisite dinner at Ramsay’s Kitchen by Gordon Ramsay. Hotel - Four Seasons Hotel St. Louis
Day 4 St Louis, Missouri to Oklahoma City, Oklahoma (500 miles)
Oklahoma City, Oklahoma
The journey from St. Louis takes you deeper into classic Route 66 country, blending wide-open plains with authentic Western Americana. Cruising southwest on I-44, you’ll pass through Missouri’s rolling Ozark foothills into Oklahoma’s flat, sun-soaked landscapes. Near Springfield, make a fast stop at the Route 66 Car Museum for a quick walk through automotive history. In Tulsa, pause for a photo of the iconic Golden Driller statue. The real Western immersion begins in Oklahoma City. A must-see is the National Cowboy & Western Heritage Museum, filled with art, cowboy gear, and Native American exhibits. This fast-paced drive is rich with roadside legends and a bold western edge, making the journey as memorable as the destination. Hotel - Fordson Hotel
Day 5 Oklahoma City, Oklahoma to Amarillo, Texas (260 miles)
Amarillo, Texas
Hit the road for your four-hour drive to Amarillo, pausing at the turn-of-the-century Goff House in El Reno and crossing the iconic Pony Bridge in Bridgeport — a classic Route 66 landmark. Step back into 1950s Americana at Lucille’s Service Station, then enjoy a playful stop at the Volkswagen Slug Bug Ranch, leaving your mark on the spray-painted cars. Arrive in Amarillo and settle in for the night at The Barfield Hotel.
Day 6 Amarillo, Texas to Santa Fe, New Mexico (280 miles)
Santa Fe, New Mexico
Make the five-hour journey to Santa Fe. Before you leave Amarillo, make sure to visit Historic 6th Street, which offers a nostalgic stroll through the past with eclectic shops, art galleries, and classic diners. Stop at the Midpoint Café and Bent Door Midway Station for a bite, then pass through the ghost town of Glenrio on the Texas–New Mexico border. Finally, in Santa Rosa, the Auto Museum awaits, providing a fascinating collection of classic cars and memorabilia.. Hotel - Four Seasons Hotel Sante Fe
Day 7 Santa Fe, New Mexico
Today, embark on a half-day private walking tour of Santa Fe's historic Plaza and Barrio de Analco with an expert guide boasting nearly 40 years of experience. Explore the oldest U.S. capital, uncovering its Native American, Spanish, and American history from 1610 to its role in the Manhattan Project. Trace the evolution of its unique architecture and vibrant art market. The tour includes visits to the Cathedral Basilica to see the oldest Marian statue, the Loretto Chapel's Miraculous Stairway, and the San Miguel Mission, the continent's oldest church.
Day 8 Santa Fe, New Mexico
Today, embark on a full-day private journey into New Mexico's past with an expert guide. Travel from Santa Fe through the scenic Jemez Mountains to Bandelier National Monument. Explore the ancestral Puebloan world on the Pueblo Loop Trail, seeing the Tyuonyi pueblo, cliff dwellings, and ancient rock art. Then, travel the back road to Los Alamos for a chronological walking tour of its Historic District, from ancient Pueblo remains to the era of the Ranch School and the Manhattan Project. After this enriching immersion into history, your guide will accompany you back to your Santa Fe hotel.
Day 9 Santa Fe, New Mexico to Canyon Point, Utah (450 miles)
Canyon Point
Today, embark on a scenic 7-hour self-drive from Santa Fe to Lake Powell/Page for check-in at Amangiri. This cross-desert journey leads to a stunning region of blue waters and towering sandstone cliffs, offering boating, hiking, and exploration. Your destination, Amangiri, is a secluded luxury resort renowned for its minimalist design and panoramic desert views. It provides a tranquil base for adventure, with a world-class spa, exceptional dining, and access to natural wonders like nearby slot canyons and Monument Valley, blending ultimate relaxation with the raw beauty of the landscape.
Day 10 Amangiri, Utah
Today is yours to enjoy Amangiri’s luxurious amenities at leisure. Take a hike at sunrise or sunset and allow the long shadows and glow of the sky to envelop you in comfort and peace. Enjoy the iconic pool or your private plunge pool; take part in daily complimentary group hikes; or stretch out at a morning group yoga session or an afternoon Pilates class.
Staying at
Amangiri
Day 11 Canyon Point, Utah to Grand Canyon, Arizona (160 miles)
This morning, check out of Amangiri and begin your 3-hour self-drive to the Grand Canyon South Rim. Upon arrival, meet your private naturalist guide for a tailored 3-hour tour. Enjoy exclusive vehicle access beyond public barricades for an expedited journey to the park's most spectacular highlights. Your guide will illuminate the canyon's profound geology, ecology, and human history during a captivating walking tour. After this immersive experience, you will be transferred back to your vehicle to check in at The Grand Hotel, your comfortable base in Tusayan, where the remainder of your day is at leisure.
Day 12 Grand Canyon, Arizona to Sedona, Arizona (110 miles)
Sedona
Today, embark on a breathtaking 2.5-hour drive from the Grand Canyon to Sedona. The journey begins with final canyon vistas from the Desert View Watchtower before winding through the Kaibab National Forest. After passing through Flagstaff, you'll descend dramatically into Sedona's iconic red-rock country, greeted by towering spires and vivid cliffs. Your destination is the luxurious Ambiente: A Landscape Hotel, where floor-to-ceiling glass blurs the line between your elegant accommodations and the stunning, surreal desert landscape, offering a front-row seat to Sedona's natural beauty for the rest of your day at leisure.
Day 13 Sedona, Arizona
This morning, embark on a private guided hike to experience Sedona's majestic landscapes. Your 3-hour, easy-to-moderate trek covers 2-3 shaded miles, designed to showcase iconic formations like Cathedral Rock. An early or late afternoon start ensures a tranquil, cool journey away from crowds. Your knowledgeable guide will share the area's sacred lore while leading you past meandering creeks and through serene woodlands. With all necessary gear, water, and snacks provided, you can fully immerse yourself in the stunning scenery. After your breathtaking adventure, you'll be returned to your hotel to enjoy the remainder of your day at leisure.
Day 14 Sedona, Arizona to Las Vegas, Nevada (300 miles)
Journey toward the vibrant lights of Las Vegas, stopping at Pete’s Gas Station Museum — a time capsule of vintage vehicles and preserved station aesthetics — followed by the Ash Fork Route 66 Museum and the De Soto Saloon. Continue to Seligman to visit Angel & Vilma Delgadillo’s quirky Route 66 Gift Shop and the retro Aztec Motel, keeping classic Americana style alive. Arrive in Las Vegas and check in at Encore before enjoying VIP seating at a Cirque du Soleil show, immersing yourself in the city’s glamourous nightlife.
Day 15 Las Vegas, Nevada to Palm Springs, California (240 miles)
Make the five-hour drive to Palm Springs, stopping in Barstow to explore the Route 66 Mother Road Museum, filled with historic photos and artefacts from the Mojave Desert. Continue to Helendale to see Elmer’s Bottle Tree Ranch, a whimsical forest of colourful glass art, and tuck into a classic diner lunch at Emma Jean’s Holland Café.
Day 16 Palm Springs, California to Santa Monica, Los Angeles (150 miles)
This morning, join your naturalist guide for an off-the-beaten-path hike in Joshua Tree National Park before you set out on the final stretch of your Route 66 adventure — a three-hour drive from Palm Springs to Santa Monica. Pass through San Bernardino to see the original McDonald’s site and make one last nostalgic stop at a classic gas station in Rancho Cucamonga before reaching the Pacific. Spend your final day discovering Los Angeles with an insider tour of the city or cycle along Santa Monica and Venice Beach, soaking up California’s laid-back coastal energy. Enjoy your final two-night stay at Regent Santa Monica — an exclusive beachfront haven.
Day 17 Santa Monica
Experience Southern California's iconic beauty on a guided 2-hour e-bike tour from Santa Monica to Venice Beach. Glide effortlessly along winding coastal paths with sweeping ocean views. Your guide will provide fascinating stories about landmarks, from the vibrant Venice Boardwalk with its performers and canals to the classic Santa Monica Pier. Bikes, helmets, and water are delivered to you. After exploring these legendary beaches and their hidden inland gems, your guide returns you to your hotel to freshen up, perfectly setting the stage for a leisurely lunch. Hotel - Regent Santa Monica
Day 18 Depart Los Angeles
Check out of your hotel and drop your rental vehicle at the airport for your return flight home.
Lucy
Travel Specialist
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18 nights from £21,945 per person
