Itinerary
- Day 1
Chicago
You'll arrive in Chicago at your own pace and head to Palmer House Hilton to settle in. If you get there early, the city offers plenty to explore on your own. The Adler Planetarium is worth the trip if you're into that sort of thing, and the Frank Lloyd Wright Historic District over in Oak Park shows some real architectural history. Downtown has its own energy, and the Skydeck puts you 1,450 feet up for some serious city views. None of that's required though. Later in the evening, everyone meets up for a welcome dinner with the group.
- Meals
- Dinner (Welcome dinner)
- Accommodation
- Hotel
Included Activities
- Welcome dinner
Optional Activities
- Visit Adler Planetarium
- Explore Frank Lloyd Wright Historic District in Oak Park
- Stroll through city center
- View from Skydeck (Chicago's tallest building)
Landmarks/POIs Adler Planetarium Frank Lloyd Wright Historic District Skydeck 
- Day 2
Chicago to Springfield
Morning starts at Eagle Rider Station where you'll pick up your motorcycle and get ready to ride. From there it's south on legendary Route 66 through the Pontiac Trail area, passing through Juliet. There's a Route 66 Museum along the way if history interests you. You'll cover about 186 miles before rolling into Springfield for the night, which gives you a proper introduction to what riding this route feels like.
- Meals
- Breakfast (Small breakfast on travel days)
Included Activities
- Motorcycle rental and pickup at Eagle Rider Station
- Route 66 ride from Chicago to Springfield
Optional Activities
- Stop at Route 66 Museum
Landmarks/POIs Route 66 Route 66 Museum 
- Day 3
Springfield to St. Louis
You're crossing into Missouri today, heading toward St. Louis where the Mississippi River runs and that famous Gateway Arch rises up as the symbol of westward expansion. The ride takes you through the heart of America with cornfields stretching out and small towns scattered along Route 66. After roughly 116 miles of riding, you'll pull into St. Louis and see what the city's got to offer along the river.
- Meals
- Breakfast (Small breakfast on travel days)
Included Activities
- Route 66 ride to St. Louis
Landmarks/POIs Gateway Arch - Day 4
St. Louis to Joplin
This stretch includes Devils Elbow, one of the most scenic parts of Route 66 where the landscape changes noticeably. You'll see different terrain as you move through Missouri. There's a chance to stop and meet Gary, a Route 66 legend, at Gay Parita's, which adds some real character to the day. By the end of about 333 miles of riding, you'll roll into Joplin where you can rest up.
- Meals
- Breakfast (Small breakfast on travel days)
Included Activities
- Route 66 ride through Devils Elbow
- Meet Route 66 icon Gary at Gay Parita's
Landmarks/POIs Devils Elbow Gay Parita's - Day 5
Joplin to Oklahoma City
Heading west now, the terrain gets rolling as you enter Oklahoma, which became a state back in 1907. The landscape here tells the story of Native American heritage in real, visible ways. You'll pass through country that's different from what you've seen so far on the ride. After about 254 miles, Oklahoma City comes into view for the night.
- Meals
- Breakfast (Small breakfast on travel days)
Included Activities
- Route 66 ride to Oklahoma City
Landmarks/POIs Oklahoma - Day 6
Oklahoma City to Amarillo
Texas is calling, so you head out in the morning riding the historic Chisholm Trail through Yukon and El Reno. Clinton has another Route 66 Museum if you want to stop and stretch. Keep going to Amarillo, and if you're hungry by then, the Big Texan Steakhouse is the place locals point to for steaks. The day covers about 265 miles of riding before you settle in for the night.
- Meals
- Breakfast (Small breakfast on travel days)
Included Activities
- Route 66 ride to Amarillo
Optional Activities
- Stop at Route 66 Museum in Clinton
- Dine at Big Texan Steakhouse
Landmarks/POIs Route 66 Museum Big Texan Steakhouse - Day 7
Amarillo to Santa Fe
New Mexico's waiting, and the ride heads west through some iconic spots. Cadillac Ranch is something you've probably seen in pictures, so that's worth stopping for. Then there's Adrian, Texas, before you move into Comanche country and the High Plains. Santa Fe sits at the end after about 302 miles, and this city mixes Spanish and Native American cultures in ways you'll feel as you walk around. You're staying two nights here, so take time to look around.
- Meals
- Breakfast (Small breakfast on travel days)
Included Activities
- Route 66 ride to Santa Fe
- Pass through Cadillac Ranch
- Stop in Adrian, Texas
Landmarks/POIs Cadillac Ranch - Day 8
Santa Fe to Albuquerque
The ride wraps up this morning when you return your motorcycle in Albuquerque. It's time to think back on the journey from Chicago all the way across Route 66 through the American Southwest, and everything that happened along those miles.
Included Activities
- Motorcycle handover in Albuquerque
