Centennial Historic Route 66

Fly from the UK to Chicago, USA. Your Route 66 adventure begins as you arrive in Chicago, the official starting point of America’s most legendary highway. After landing at Chicago, make your way to the hotel and settle in. Later this afternoon or evening, you’ll meet your Tour Director at the Hospitality Desk, where the excitement truly starts. The rest of the day is yours to relax, explore nearby neighbourhoods or soak up the buzz of this iconic Midwestern city before the journey west begins.

This morning, enjoy an included guided city tour showcasing Chicago’s world-famous skyline and architectural heritage. Marvel at pioneering designs by legends such as Frank Lloyd Wright, Mies van der Rohe and Daniel Burnham as you explore the Magnificent Mile, Navy Pier and the city’s beautiful lakefront parks. See Cloud Gate, affectionately known as “The Bean,” before enjoying free time this afternoon. You may choose to visit the Willis Tower, take an architectural river cruise or enjoy a memorable dinner cruise, all bookable through your Tour Director.

Today, leave Chicago behind and officially begin your journey along Historic Route 66. Traveling west through classic Midwestern landscapes of cornfields and open prairies, you’ll follow the original east-to-west path taken by millions before you. Arriving in St. Louis, one of Route 66’s most significant cities, you’ll have the chance to see the iconic Gateway Arch, the symbolic “Gateway to the West.” This striking monument marks a pivotal chapter in America’s westward expansion and Route 66 history.

Continue into southern Missouri and the rolling Ozark Highlands, often regarded as the birthplace of Route 66. Along the way, visit the impressive Meramec Caverns, a vast limestone cave system filled with dramatic formations and rich colour. As you explore underground chambers and winding passages, you’ll hear stories of outlaw Jesse James, who once used these caves as a hideout. This fascinating blend of natural beauty and Wild West folklore offers a memorable taste of early Route 66 adventure.

This morning, the road leads briefly through southeastern Kansas before entering Oklahoma, the state with the longest drivable stretch of Route 66. This historic route once carried Dust Bowl families west in search of opportunity during the 1930s. Along the way, spot beloved roadside icons including the famous Blue Whale of Catoosa. Pass through Tulsa, crossing the historic Avery Route 66 Memorial Bridge, before arriving in Oklahoma City. A brief orientation tour introduces you to the state capital and its Route 66 legacy.

Travel west through wide-open landscapes toward Amarillo, set in the vast plains of the Texas Panhandle. En route, stop at the Oklahoma Route 66 Museum in Clinton, where interactive exhibits bring six decades of Route 66 history vividly to life. Continue through Shamrock, Texas, famous for its classic art-deco U-Drop Inn, and pause for photos at a restored 1929 Phillips 66 petrol station in McLean. These nostalgic stops capture the spirit of America’s golden age of road travel.

Before leaving Amarillo, visit the world-famous Cadillac Ranch, one of Route 66’s most photographed landmarks. Ten brightly painted Cadillacs, buried nose-down in the earth, create a quirky and unforgettable art installation. Continue west into New Mexico, where desert landscapes and vibrant culture signal a shift in scenery. Arrive in Albuquerque, the state’s largest city, known for its creative arts scene, cutting-edge technology and its annual International Balloon Fiesta, which fills the skies with colour each autumn.

Depart Albuquerque and journey to Gallup, one of Route 66’s best-preserved towns. With its glowing neon signs and vintage storefronts, Gallup feels like a step back in time. Browse distinctive Southwestern shops before continuing into the vast lands of the Navajo Nation, the largest Native American reservation in the United States. This afternoon, you may choose an optional excursion to Canyon de Chelly, where ancient cliff dwellings, rock art and dramatic canyon walls offer a powerful introduction to Navajo history and culture.

Today’s journey takes you deep into the heart of the American Southwest. Travel through Navajo Nation lands to Monument Valley, where towering mesas and sandstone buttes create one of the most iconic landscapes in the world. This dramatic setting has starred in countless films, from classic westerns to modern favourites. An optional guided jeep tour allows you to explore the valley up close. Continue onward to Page, Arizona, where you’ll spend the night surrounded by striking desert scenery.

Before departing Page, you’ll have the opportunity to join an optional visit to breathtaking Antelope Canyon, famed for its narrow sandstone corridors sculpted by wind and water. Later, travel to the awe-inspiring Grand Canyon, one of the world’s greatest natural wonders. Take time to absorb its vast scale and layered colours before continuing to the historic Route 66 town of Williams. Here, enjoy an included train journey through Grand Canyon National Park, offering a truly unforgettable perspective of this legendary landscape.

Leaving Williams, rejoin Historic Route 66 and stop in Seligman, the town credited with preserving the route’s historic designation. Friendly locals and colourful storefronts celebrate Route 66 nostalgia at its best. Continue through Kingman before arriving in the dazzling city of Las Vegas. Known for its neon lights, grand resorts and nonstop entertainment, Las Vegas offers a striking contrast to the open road. This evening, you may join an optional orientation tour to discover some of the city’s most famous sights.

Today is yours to enjoy Las Vegas at your own pace. Explore the iconic Strip, wander through themed resorts or simply relax and people-watch. Your Tour Director can assist with optional excursions, including a visit to the engineering marvel of Hoover Dam or a memorable dinner and show experience this evening. Whether you’re drawn to glitz, spectacle, or hidden gems off the Strip, Las Vegas delivers unforgettable moments around every corner.

After a relaxed morning, pause at the legendary “Welcome to Las Vegas” sign for photos before crossing the Mojave Desert into California. Stop at Calico Ghost Town, a restored former silver-mining settlement that brings the Old West vividly back to life. Once abandoned during the Great Depression, it now offers a fascinating glimpse into frontier history. Continue west to Los Angeles, a sprawling metropolis and cultural powerhouse, marking the final major chapter of your Route 66 journey.

Enjoy a comprehensive city tour of Los Angeles, visiting many of its world-famous neighbourhoods. Explore downtown, stroll Hollywood’s Walk of Fame and soak up the atmosphere at Farmers Market and The Grove. Pass through glamorous Beverly Hills before reaching Santa Monica, the official end of Route 66. Spend time at the beach and iconic pier, home to the celebrated “End of the Trail” sign. This evening, gather for a farewell dinner as your unforgettable Route 66 adventure comes to a close.

Today, bid farewell to the West Coast as you depart Los Angeles for your return journey to the UK, taking home incredible memories of America’s most iconic road trip.