Ever since I can remember, I’ve dreamed of traveling the iconic Route 66. Growing up in Melbourne, Australia, I always loved cars. I loved watching car movies and live racing, collecting Matchbox and Hot Wheels cars, and taking lots of road trips as a family.
As I grew up, my toy cars were replaced with real ones. And I found someone who shared my passions for cars and road trips, my father-in-law and friend, Ivan. Together, we made a plan to live out both of our dreams to drive Route 66 across the United States to celebrate Ivan’s 60th birthday in 2015.
Stepping back in time
We wanted to experience Route 66 in a classic American car. What car is more iconic and synonymous with luxury, class, comfort and road trips than a Cadillac? Keeping a secret from Ivan, I bought the most amazing custom blue metallic 1956 Cadillac in California that was restored with a later model 500 cubic inch V8 (from a 1974 Caddy).
Then came news from my beautiful wife Jessica. We were expecting our second child. So as not to derail our trip, we revised our plans to drive caravan style. Jessica would drive in an SUV with her mom and our two children. Ivan and I would drive the ’56 Caddy.
It’s all in the details
The trip — 4,000 kilometers (2,500 miles) — in a 60-year-old unreliable car with no air conditioning and my family (new 3-month-old baby in tow), sounds like a great plan but did I mention an unreliable car? Even though I added seat belts (not essential in 56), checked the brakes, tires and all the essentials, reliability was a challenging component to our Route 66 trip. The car was fine in winter time drive tests but was struggling in the summer time heat. Adding a much larger engine from 1974 with more cooling devices drained on the electricals, causing more challenges however, we pressed on.
Heading out
Our adventure began where Route 66 begins … Chicago, Illinois, USA. We piled into our cars and headed toward our first stop, Joliet, Illinois, home of the famous jail from the 1980 Blues Brothers film. Next, we found the Launching Pad in Wilmington, Illinois. Once an iconic drive-in restaurant, now closed but we took a few photos in front of the 9 meter (30 foot) tall giant fiberglass statue and continue on our way to Pontiac, Illinois for a stop at the Route 66 Association Hall of Fame and Museum for a look at all the cool memorabilia and the Pontiac Oakland Museum. To my surprise, the Caddy held up on the first day and we arrived at the Route 66 Hotel and Conference Center in Springfield, Illinois. Finally, a chance for a cool beer at the pool and some reflection. Day one was a great start to our adventure.
Day two: We set off to St. Louis, Missouri, USA, stopping along the way for photos at historic roadside attractions or antique stores. This was a much shorter day of driving and we were happy to see the St. Louis Gateway Arch on our arrival.
Day three: It’s off to Springfield, Missouri in route to the iconic Best Western Route 66 Rail Haven, which dates back to 1938, the year Route 66 was completed. Elvis Presley actually stayed at this motel and we spent the night in a special tribute room designed for “The King.”
Day four: Our first major destination was Tulsa, Oklahoma, USA, but the Caddy had its own ideas. Fortunately, a friendly mechanic’s quick diagnosis of a minor wiring issue kept us headed toward Tulsa. Along the way we stopped in Joplin to take photos of the famous wall art and then on to the Blue Whale of Catoosa. In Tulsa, we visited the Golden Driller, a famous 21-meter (76 foot) statue that pays tribute to Oklahoma’s oil history.
After stopping for lunch at the Route 66 Museum in Clinton, Oklahoma, it was on to Amarillo, Texas, USA. We were looking forward to 2-kilogram (72 ounce) steaks and the famous Cadillac Ranch — 10 weather-beaten and spray-painted Cadillacs buried half way into the ground. We continued to Tucumcari, New Mexico, USA, and took in the many muraled walls of the city which pay tribute to notable American icons like James Dean and Elvis Presley.
Day five and six: After a busy week of long hours on the road and many stops it was now time to turn up the luxury and rest for a few days at the Four Seasons in Santa Fe, New Mexico. A beautiful city that I highly recommend.
Day seven: Time to hit the road again and head for Seligman, Arizona, USA. Along the way we stopped in Holbrook, Arizona, home of the Wigwam Hotel which inspired the Crazy Cone Hotel that was featured in Disney movie car films.
Day eight: We opted to take the longer route and visit the Grand Canyon from the South Rim, but we experienced a close call. After heading north from Flagstaff, Arizona for the Grand Canyon we did not quite calculate the distance or gas required. Our vague gauge was flickering and not enough gas to return to Flagstaff, we decided to press on. Luck was on our side and once we entered the Grand Canyon, we found a gas station that we rolled into on fumes.
We continued a long drive to Holbrook, Arizona where we took a detour off Route 66 to visit what I believe to be one of the most beautiful places in the United States — Scottsdale, Arizona.
It had to end sometime
We got back on the road as our journey neared its end stopping at the Sugar Bowl, an iconic 1950s ice cream parlour on our way to Palm Springs and finally, the end of the road, Santa Monica, California, USA. Perhaps the old Caddy knew our special time was coming to a close when it gave out about 20 miles from the Santa Monica Pier. Determined to cruise in our Caddy to the end of our journey, we found a tow truck and a mechanic to handle the repair and our dream came true. We rolled into Santa Monica just like the road travelers did for so many years before us.
The Cadillac is in happy retirement just outside Melbourne, a wonderful piece of our history and a fun reminder of our family’s incredible journey of a lifetime.
If you are planning a road trip, I’ll leave you with a few of tips to make planning your travels a bit easier:
- OneNote is a valuable tool to begin mapping out a high-level plan for your road trip. This tool will help you determine reasonable amounts of driving time, places to visit and where to have fun.
- Don’t rely on Google Maps to determine driving times. I found that often, mapping apps often are optimistic and don’t factor in your circumstances like needing to stop for diaper changes when you have a small child with you, car issues or unexpected weather delays.
- Work in some time for rest and relaxation. Driving takes its toll on the entire crew. Stopping for lunch or tourist spots don’t really provide much in the way of real rest. We found taking a day or two at a resort or nicer hotel really helps rejuvenate everyone!
YPO member Travis Knipe is Chief Executive Officer of StarRez, the world leader in student housing software in 20 countries, with more than 650 customers managing more than 1 million residence beds. Knipe is passionate about ensuring his team and customer community are happy and that his products continue to evolve and stay ahead of industry trends, emerging technology and customer needs. His interests away from business include all forms of sports, fitness, international travel, motorsports/cars/driving, and quality time with family and friends.
