The Road to Santa Monica

Arrive in Chicago and enjoy a private transfer to your hotel. The rest of the day is free to relax after your flight or begin exploring this vibrant lakeside city at your own pace.

Enjoy a privately guided tour of Chicago, known for its striking skyline and world-renowned architecture. See the Magnificent Mile, Millennium Park and Cloud Gate, Navy Pier, Grant Park and the city’s historic neighbourhoods.

Your afternoon can be tailored to your interests, with options such as an architectural river cruise, Willis Tower, world-class museums, shopping or a memorable dinner overlooking the city.

Your Route 66 journey begins as you travel southwest through Illinois’ open countryside toward St. Louis, Missouri. Along the way, discover the nostalgic landscapes and small-town Americana that made the Mother Road famous.

In St. Louis, visit the iconic Gateway Arch, a powerful symbol of America’s westward expansion.

Continue through the scenic Ozark Highlands, an important region in the early story of Route 66. Visit Meramec Caverns, a remarkable limestone cave system known for its dramatic formations and local legends surrounding Jesse James.

Arrive in Springfield, often regarded as the birthplace of Route 66, for an evening at leisure.

Travel through a corner of Kansas and into Oklahoma, home to the longest drivable section of historic Route 66. Stop at the famous Blue Whale of Catoosa and discover Tulsa’s Route 66 heritage.

Continue to Oklahoma City, where you may enjoy a private orientation tour of the state capital before checking into your hotel.

Today’s journey takes you west through the Great Plains toward Amarillo, Texas. Visit the Oklahoma Route 66 Museum in Clinton and explore the history of this iconic highway.

Continue with photo stops at Shamrock’s Art Deco Conoco Tower Station and U-Drop Inn Café, as well as the restored Phillips 66 station in McLean.

Begin the day at Cadillac Ranch, Amarillo’s famous outdoor art installation featuring ten classic Cadillacs planted nose-first in the Texas soil.

Continue west into New Mexico and arrive in Albuquerque, a city known for its Native American and Hispanic heritage, colourful arts scene and beautiful desert setting.

Travel west to Gallup, one of Route 66’s most authentic communities, known for its vintage neon signs, trading posts and Southwestern character.

Continue into Navajo Nation, the largest Native American reservation in the United States. An optional private experience at Canyon de Chelly can be arranged, offering dramatic canyon views, ancient cliff dwellings and insight into Navajo culture.

Today, travel through the Navajo Nation to Monument Valley, one of the most recognisable landscapes in the American West. Its monumental sandstone buttes and mesas have provided the backdrop for countless classic films.

A private Navajo-guided jeep tour can be arranged for an immersive look at this extraordinary landscape. Continue to Page for the evening.

This morning, choose an optional guided visit to Antelope Canyon, where wind and water have shaped narrow sandstone passageways into a breathtaking natural masterpiece.

Later, travel to Grand Canyon National Park. Enjoy time at the rim to take in one of the world’s most spectacular views before continuing to Williams, a charming Route 66 town near the canyon.

Travel along one of the most memorable sections of Route 66, stopping in Seligman, a colourful town that helped preserve the legacy of the historic highway.

Continue via Kingman to Las Vegas. This evening, relax at your luxury hotel or enjoy a privately arranged evening experience, from a helicopter flight over the Strip to a world-class show or fine-dining reservation.

Enjoy a day entirely at your leisure in Las Vegas. Your specialist can arrange a private visit to Hoover Dam, a Red Rock Canyon excursion, spa time, shopping, a gourmet dining experience or tickets to one of the city’s renowned shows.

Leave Las Vegas and cross the Mojave Desert into California. Stop at the famous Welcome to Fabulous Las Vegas sign before visiting Calico Ghost Town, a restored 19th-century silver-mining settlement.

Continue to Los Angeles, where you will settle into your hotel for the evening.

Explore Los Angeles with a private guide. See Hollywood, the Walk of Fame, Beverly Hills, Farmers Market, The Grove and selected neighbourhoods that reflect the city’s unique character.

Later, arrive in Santa Monica, the western end of Route 66. Enjoy time to walk the beach, explore Santa Monica Pier and photograph the famous “End of Route 66” sign. Celebrate your journey with a special farewell dinner.

After breakfast, enjoy a private transfer to Los Angeles International Airport for your onward flight.

Tailor Your Private Route 66 Journey

This itinerary is fully customizable. We can adjust the pace, hotel style, sightseeing, dining and experiences to create a Route 66 journey that feels entirely your own from boutique stays and luxury resorts to private guides, scenic flights and exclusive cultural encounters.