Itinerary
- Day 1
Chicago
You'll arrive in Chicago and head to the Palmer House hotel on your own. Depending on your flight time, there's plenty to explore around the city. Check out the Adler Planetarium for space exhibits, or head to the Frank Lloyd Wright Historic District in Oak Park to see his architectural work. You could also wander downtown or ride the Skydeck up the Willis Tower for views across the city. In the evening, you'll meet the group for a welcome dinner.
- Meals
- Dinner (Welcome dinner together)
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 Adler Planetarium Frank Lloyd Wright Historic District Skydeck 
- Day 2
Chicago to Springfield
This morning you'll head to Eagle Rider Station to pick up your Harley-Davidson motorcycle. Then it's time to hit the legendary Route 66 heading south through the Pontiac Trail, passing through Juliet where you can optionally stop at the Route 66 Museum if you want. The ride south covers about 186 miles (299 km) and ends in Springfield for the night.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Motorcycle pickup and orientation at Eagle Rider Station
- Route 66 motorcycle ride from Chicago toward Springfield
Optional Activities
- Stop at RT 66 Museum
Landmarks Route 66 Museum 
- Day 3
Springfield to St. Louis
You'll cross from Illinois into Missouri as you ride toward St. Louis. The Gateway Arch comes into view as you approach the city sitting on the Mississippi River. Along the way, you'll pass through cornfields and small towns that show you the interior landscape of America. This segment covers roughly 115 miles (186 km) to St. Louis.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride to St. Louis
- View Gateway Arch
Landmarks Gateway Arch - Day 4
St. Louis to Joplin
Today takes you through one of Route 66's most beautiful sections at Devils Elbow as you head toward Joplin. Missouri's landscape changes around you with varied terrain and scenery. You'll stop to meet Gary, a Route 66 icon, at Gay Parita along the way. This is a longer day with approximately 333 miles (536 km) to Joplin.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride through Devils Elbow
- Stop to meet Route 66 icon Gary at Gay Parita's
Landmarks Devils Elbow Gay Parita's - Day 5
Joplin to Oklahoma City
You'll head west over rolling hills into Oklahoma, which became a state back in 1907. Native American history connects deeply to this region, and you'll see evidence of that heritage as you ride through. The day covers about 253 miles (408 km) into Oklahoma City.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride into Oklahoma
- Day 6
Oklahoma City to Amarillo
Start heading toward Texas by riding the Chisholm Trail through Yukon and El Reno. There's a stop planned at the Route 66 Museum in Clinton to break up the ride. You'll reach Amarillo by evening, and the Big Texan Steakhouse is worth a visit if you're hungry for some of the state's best steaks. This stretch covers around 265 miles (426 km).
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride to Amarillo
- Stop at Route 66 Museum in Clinton
Optional Activities
- Dinner at Big Texan Steakhouse
Landmarks Route 66 Museum Big Texan Steakhouse - Day 7
Amarillo to Santa Fe
Now you're heading into New Mexico. You'll pass through the world-famous Cadillac Ranch and stop in Adrian, Texas before continuing. The ride takes you through Comanche country and the High Plains until you reach Santa Fe by evening. Spanish and Native American influences shape the city's unique character. The day's ride is about 301 miles (485 km), and you're staying two nights here.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride to Santa Fe
- Pass through Cadillac Ranch
Landmarks Cadillac Ranch - Day 8
Santa Fe
You'll spend the whole day exploring Santa Fe without riding. The city holds historical, artistic, and cultural treasures that reflect Spanish and Native American heritage blended together. Walk through different neighborhoods to see the distinctive architecture, colorful buildings, art galleries, fashion boutiques, and interior design shops that make Santa Fe the center of Southwest culture.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Free day to explore Santa Fe
- Day 9
Santa Fe to Gallup
Heading south through Albuquerque and along the Rio Grande into Navajo territory. You'll continue past the Cibola National Forest on your way to Gallup, a railroad town with deep significance to Native American communities. This day covers approximately 269 miles (434 km).
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride to Gallup
- Travel through Navajo wilderness
- Pass through Cibola National Forest
Landmarks Cibola National Forest - Day 10
Gallup to Grand Canyon
You'll cross into Arizona and make your way to Petrified Forest National Park to see the fossilized trees scattered across the landscape. After exploring the park, you continue through Flagstaff heading toward the Grand Canyon, one of the trip's main highlights. By evening you'll be watching the sunset with a drink in hand, taking in the view. Today's ride is roughly 341 miles (550 km).
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride through Arizona
- Visit Petrified Forest National Park
- Arrive at Grand Canyon for sunset viewing
Landmarks Petrified Forest National Park Grand Canyon - Day 11
Grand Canyon to Laughlin
Start the morning with a helicopter flight over the Grand Canyon's South Rim for a different perspective of this landscape. After landing, you'll ride along the canyon's edge with several stops for photos and views. Then you'll return to Route 66, stopping in places like Seligman before reaching Laughlin. The riding portion covers about 255 miles (410 km).
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Helicopter flight over Grand Canyon South Rim
- Ride along Grand Canyon edge with photo stops
- Route 66 motorcycle ride to Laughlin
Landmarks Seligman - Day 12
Laughlin to Las Vegas
You'll start by riding through the old ghost town of Oatman, then head over the famous Hoover Dam. After that, it's into Las Vegas with all its lights, casinos, and entertainment. This shorter day covers roughly 130 miles (210 km).
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride through Oatman ghost town
- Cross Hoover Dam
- Arrive in Las Vegas
Landmarks Oatman Hoover Dam - Day 13
Las Vegas to Victorville
Today brings you toward California, the final state on this journey. You'll ride through the Mojave Desert where the silence is complete and the colors shift across the landscape as you travel through the vast terrain. The day covers approximately 281 miles (452 km) to Victorville.
- Meals
- Breakfast (Small breakfast on travel day)
Included Activities
- Route 66 motorcycle ride through Mojave Desert to California
- Experience Mojave Desert landscape
Landmarks Mojave Desert - Day 14
Victorville to Los Angeles
The final stage takes you to Los Angeles on the Angeles Crest Highway through the mountainous Angeles National Forest, climbing over 7,500 feet through some of Southern California's best motorcycle roads. You'll reach the iconic 'End of the Trail' sign at Santa Monica Pier, completing your Route 66 adventure. After dropping off your motorcycle at Eagle Rider Station, you'll transfer to the hotel for a farewell dinner to reflect on the journey. The final ride is about 123 miles (199 km).
- Meals
- Breakfast (Small breakfast on travel day), Dinner (Farewell dinner)
- Accommodation
- Hotel
Included Activities
- Route 66 motorcycle ride to Los Angeles
- Ride Angeles Crest Highway through Angeles National Forest
- Arrive at Santa Monica Pier End of Trail sign
- Motorcycle return to Eagle Rider Station
Landmarks Angels Crest Highway Angels National Forest Santa Monica Pier - Day 15
Los Angeles
This is your departure day. You can head home, or if you'd prefer to stay longer and explore more of Los Angeles, you have the option to extend your trip.
