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5-Day Route 66 Adventure Itinerary
Last updated: 2024 Jun 30Kickoff in Chicago
Morning
Start your journey at the iconic Route 66 Start Sign. This is where the historic Route 66 begins. Take some time to snap photos and soak in the excitement of starting your road trip.
Afternoon
Head over to Willis Tower Skydeck for a breathtaking view of Chicago from above. The Skydeck offers an unparalleled perspective of the city and is a must-see landmark.
Evening
Conclude your day with a visit to Navy Pier. Enjoy the vibrant atmosphere with various dining options and entertainment. The pier is beautifully lit up at night and offers a perfect end to your first day.
Bedtime
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Exploring St. Louis
Morning
Drive to St. Louis and start your day with a visit to the Gateway Arch. This iconic monument symbolizes the westward expansion of the United States and offers stunning views from its observation deck.
Afternoon
After lunch at Pappy's Smokehouse, head over to Missouri Botanical Garden. The garden is one of the oldest botanical institutions in the United States and features beautiful landscapes and unique plant collections.
Evening
Spend your evening exploring Laclede's Landing, a historic district known for its cobblestone streets and vibrant nightlife. Enjoy dinner at one of the many restaurants or bars in the area.
Bedtime
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Charming Tulsa
Morning
Arrive in Tulsa and start with a visit to Philbrook Museum of Art. This museum is housed in an Italian Renaissance villa and features an extensive collection of art from around the world.
Afternoon
After lunch at Burn Co BBQ, explore Gathering Place, a world-class park offering numerous activities including walking trails, playgrounds, and gardens.
Evening
End your day with a stroll through Brady Arts District, known for its vibrant arts scene. Enjoy dinner at one of the local eateries or catch a live performance at one of the district's venues.
Bedtime
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Amarillo Adventures
Morning
Begin your day with a visit to the Cadillac Ranch. This unique public art installation features half-buried, graffiti-covered Cadillacs and is a must-see for anyone traveling Route 66.
Afternoon
After lunch at The Big Texan Steak Ranch, head over to the Amarillo Museum of Art. The museum offers a diverse collection of artworks and often hosts temporary exhibitions.
Evening
Conclude your day with a visit to the Texas Air & Space Museum. Explore the history of aviation and space exploration through various exhibits and displays.
Bedtime
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Santa Fe Serenity
Morning
Georgia O'Keeffe Museum is a great way to start your day in Santa Fe. The museum showcases the works of Georgia O'Keeffe, one of America's most iconic artists.
Afternoon
Canyon Road is perfect for an afternoon stroll. This historic street is lined with art galleries, boutiques, and cafes. It's an ideal place to explore local art and culture.
Evening
Santa Fe Plaza is the heart of Santa Fe's historic district. Enjoy dinner at one of the nearby restaurants and take in the vibrant atmosphere. The plaza often hosts live music and events in the evening.
Bedtime
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