Day 1 - Chicago

On the shores of Lake Michigan, the ‘Windy City’ has something for everybody. A great destination at any time of the year, Chicago has a beautiful lakefront, breath-taking architecture, world-class shopping, wonderful museums, great theatres, gourmet restaurants and fantastic nightlife. Discover the delights of the Magnificent Mile, get a bird's eye view of the city from the 360 Chicago Observation Deck or from the Ledge at the Skydeck. If heights aren’t your thing take a stroll in Grant Park for a more relaxing option, visit the Shedd Aquarium, take a boat tour or walk on the beach. Don’t miss Navy Pier, where new Route 66 signage marks the beginning of the road, and at Lou Mitchell’s legendary Route 66 café on Jackson Boulevard. Restaurants and nightlife abound throughout the city, with live music venues, theatres, world class restaurants and bars. 

Stay two nights in Chicago.

Day 3 - Chicago to Alton, IL – approx. 4 hours

Head out of the city and across the state of Illinois to the Mississippi River. Alton is a scenic Mississippi River town known for its rich history, beautiful riverfront, and outdoor recreation. Whilst not a Route 66 town, Alton is on another scenic roadway – the Great River Road, and you can enjoy breathtaking views of the Mississippi from here. Discover some unique shops, restaurants such as Fast Eddies Fried Chicken or the Old Bakery Beer Company, and local attractions, including a life-size statue of Robert Wadlow, who at 8ft 11, was the world’s tallest man.

Stay one night in Alton.

Day 4 - Alton to Kansas City, MO – approx. 7 hours

Immerse yourself in a vibrant urban scene filled with world-class jazz, mouthwatering barbeque, and buzzing neighbourhoods. Explore KC as it’s known, on foot or by the free streetcar, which will whisk you between neighbourhoods boasting shopping, dining, museums and nightlife. Some of the city’s key highlights include the National WWII Museum, the Nelson-Atkins Museum of Art and the Kemper Museum of Contemporary Art, and not forgetting the world’s first Museum of BBQ where you’ll learn everything and more about BBQ and why it’s such a staple in Kansas City.

Stay two nights in Kansas City. 

Day 6/7 - Alton to Trinidad, CO – approx. 11 ½ hours (overnight)

Trinidad is nestled between Fishers Peak mesa and the Spanish Peaks, at the edge of the Rocky Mountains, and surrounded by beautiful scenery. It is known for its rich history having been on the Santa Fe Trail, a vital 19th-century trading route and stopping point for pioneers, trappers, and traders. It has a very well preserved downtown with some beautiful Victorian architecture, thriving arts scene and outdoor activities.

Stay one night in Trinidad.

Day 8 Trinidad to Gallup, NM – approx. 10 hours

Arriving in Gallup in the evening, you will have to wait until the morning to explore this Route 66 town surrounded by red rock scenery. Often called the "Gateway to Native America," Gallup is a threshold to its multiple indigenous neighbours and celebrates the rich arts and centuries old cultural traditions that come with being a western railroad border town. You’ll find murals, galleries and Native American jewellery stores, along with a Route 66 ‘Muffler Man’, some iconic neon signs and roadside diners. 

Stay one night in Gallup.

Day 9 - Gallup to Winslow, AZ – approx. 2 hours

Take the evening train to Winslow. More than just a Route 66 stop – civilisations have thrived in the area for centuries … the ancient Hopi village of Homolovi, the Mormon settlement of Brigham City, now a ghost town on the National Register of Historic Places and the booming town of Winslow over 100 years ago. Winslow offers a unique blend of Native American traditions, railroad legacy, and Route 66 nostalgia. Most recently the City of Winslow is known for The Standin’ on the Corner Park, which has become an interesting draw for music fans who remember the line from the Eagles’ hit, Take it Easy. 

Stay one night in Winslow.

Day 10 - Winslow to Flagstaff, AZ – approx. 1 hour

In Flagstaff many of the old brick buildings in the downtown area are original to Route 66. Be sure to visit the Museum Club a historic roadhouse that still welcomes visitors to quench their thirst after a long day on the road. If you love the smell of pine, you’re in luck because at a cool 7,000-foot elevation, Flagstaff is nestled in the world’s largest Ponderosa Pine forest. Visit the Lowell Observatory and observe the night sky, or the Museum of Northern Arizona, which provides a fascinating insight into the local history. You could also take a day trip to the Grand Canyon from here. 

Stay two nights in Flagstaff.

Day 12 - Flagstaff to Needles, CA – approx. 4 hours

Founded in 1883 along the Colorado River at California's border with Arizona, Needles was named for the sharp mountain peaks nearby. In 1908, the Santa Fe Railroad built the grand El Garces Harvey House, a combination train depot, hotel, and restaurant. Today, Needles remains a key gateway for Route 66 travellers, desert explorers, and river-recreation enthusiasts. You’ll find a Route 66 Museum, a theatre, diner, and Route 66 signage.

Stay one night in Needles.

Day 13/14 - Needles to Los Angeles, CA – approx. 8 ½ hours

Take the overnight train to Los Angeles and head for the beach city of Santa Monica, where Route 66 reaches the Pacific Ocean. Today Santa Monica is a haven for beach lovers with a boardwalk, pier, amusements, street performers, side walk cafes and bars and a true California atmosphere. Enjoy the beach, or the other sights of the Los Angeles area such as Hollywood, Beverly Hills, Universal Studios, Disneyland, or one of the museums representing the American West and Californian Heritage. Why not extend your holiday to include a bit more time to see the sights, or to relax.

Stay two nights in Santa Monica.

Day 16 - Head for the airport in time to check-in for your flight back to the UK.