19 DAY – Route 66 Guided Motorcycle Tour Via Milwaukee

Guided Tours

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Day 1 – Arrive in Chicago

We meet after lunchtime at the hotel. We also do an orientation with the bikes. Then we go out for dinner to discuss our big adventure!

Day 2 – Chicago to Milwaukee (Option 1) or Chicago to Milwaukee to Chicago (Option 2)

Let’s go! We ride on our motorcycles to the famous Harley-Davidson Museum in Milwaukee where we tour before heading out on Route 66 the next day.

Day 3 – Milwaukee (Or Chicago) to Springfield, Illinois- 185 miles

See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.

Day 4 – Springfield, Illinois to Saint Louis- 175 miles

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 5 – St Louis to Lebanon, MO – 153 miles

Riding our motorcycles on Rt 66 through neat little towns, we have really fallen into synch with our Harley Davidsons. Americana. Devils Elbow is amazing.

Day 6 – Lebanon to Tulsa, OK – 233 miles

A great section of RT 66 with all the Googie Architecture. A really great motorcycle ride on old pavement of the Mother Road. We visit some great old diners. This is RT 66!

Day 7 – Tulsa to Clinton OK – 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 8 – Clinton to Amarillo, TX – 176 miles

Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner? Everything is bigger in Texas. Let’s live a little old Route 66 today on our motorcycle and tonight. You will know you are on old Rt 66 today. It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.

DAY 9 – Amarillo  to Santa Fe, NM – 279 miles 

Cadillac Ranch is a Route 66 stop we must do. Who has ever spray painted a vintage Cadillac on Rt 66 before? Let me ask you again in the future… Welcome to Santa Fe. Art galleries, great restaurants, shopping, great walking around…. This is really an amazing Southwest town to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 on our Harley Davidson.

Day 10 – Santa Fe, NM – Layover

Relax and enjoy this great town. We can take a short nice ride up into the beautiful mountains today. Or just enjoy a full day of rest and fun.

Day 11 – Santa Fe to Gallup – 199 miles

We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”. Then lunch in Old Town Albuquerque. Next we follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940′s and 1950′s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.

Day 12 – Gallup to Grand Canyon National Park – 283 miles

We stand on a corner in Winslow, Arizona. We stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said.

Day 13 – Grand Canyon to Williams, AZ – 51 miles

Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the Western town. Or sleep.

Day 14 – Williams to Laughlin, NV – 190 miles

The quintessential Western Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman. Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow. Ribeye Steak and Mico Brewery tonight!

Day 15 – Laughlin, NV to Las Vegas, NV – 97 miles

An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 16 – Las Vegas – Layover Day

Lots to do today. We have some great optional half day rides planned. Have fun with the group or explore Vegas on your own. Tons of fun activities to do.

Day 17 – Las Vegas, NV to Big Bear Lake (or Victorville), CA – 224 miles

We take a little Rt 66 excursion up into the amazing San Bernardino mountains. A last long hard ride through the desert, we are covered in desert dust. Our bikes are covered in road grime. They and we look and feel like we really did something. We have. Then a climb up into the twisty mountains brings us to an awaiting pool in the cool alpine town of Big Bear Lake.

Day 18 – Big Bear Lake / Victorville to Santa Monica Pier! – 113 miles

It is not over yet! We ride the Rim of The World. An incredible ride on the top of a mountain range, with the clouds below. One of our most amazing rides. Then we drop into LA, freeways, civilization. We make it through all the way to the end of Route 66! The Santa Monica Pier. … let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific! We turn the bikes in at the end of the day. A victory dinner tonight!

DAY 19 – Los Angeles Departure

We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future. A shuttle will take you to the LAX.