The 2023 Pebble Beach Tour: Superlative times with superlative cars

Rolex/Tom O'Neal

The car-based events that comprise California’s annual Monterey Car Week kick into high gear on Thursday. That’s when more than 150 classic cars participating in the Pebble Beach Tour d’Elegance presented by Rolex head out on 17-Mile Drive. The Tour is an optional activity for the cars that are entered in Sunday’s Pebble Beach Concours d’Elegance; the machines that run in the Tour earn a few extra points added to their tally that could make a difference in the overall score.

What, exactly, is the “score” at a car show? The answer is an unsatisfying “It depends.” At the Pebble Beach Concours d’Elegance, where a Best of Show award is one of the most coveted prizes in the vintage-car world, there are two sets of accolades. One, called the Special Awards, is more subjective, based on technology or design innovation, while the other class awards are more rigorous. The Best of Show winner is selected from the class-winner awards.

The classes vary from year to year; in 2023, one class was for British luxury cars built after World War II called “Postwar British Luxury.” Australian David Wilke entered his 1956 Bentley, an elegant machine with a convertible body that was handbuilt by a British firm called Park Ward. The Bentley is Wilke’s only vintage car, as he prefers to collect watches. The car, however, is special because it was purchased and cherished by Wilke’s father, who passed away in 1992. Wilke recently had the Bentley restored and the car’s run on the Tour was its first major outing.

The Tour is a roughly 50-mile trip along the California coastline that provides the car owners with a chance to prove to judges that their cars are roadworthy. The class judges at Pebble are uncommonly steeped in the details of the cars they’re charged with evaluating. They focus on originality and authenticity.

At 9:00 a.m. on Thursday morning, the cars start their short journey. We rode with Wilke as he turned the first corner and passed the Rolex signpost, which fittingly has a clock at the apex. The Rolex post is a fixture of the week; it stands at many of the car shows and the historic races held concurrently at nearby WeatherTech Raceway Laguna Seca. The Pebble Beach Best of Show winner receives a special Rolex watch—a cherished prize that is similar to the one awarded to the winners of the 24 Hours of Daytona race. Rare and historically significant Rolex watches, such as those won at events or by celebrities, have recently fetched astronomical sums. A Rolex Daytona worn by Paul Newman recently was auctioned off for $17.8 million.

Wilke’s Bentley was every bit a magic carpet ride. The inline-six-cylinder engine motivates the car so quietly and smoothly that you wonder if it’s even running. The suspension is creamy and compliant, hiding even the smallest road imperfections. If there were a dictionary entry for “Elegant Cruising,” the Bentley would be the pictured machine. Wedged in the snug rear seat, we toured the coastline like a robber baron—a wonderful way to enjoy the sights of Highway 1 rather than our usual focus on carving up the curves.

A special ride in an heirloom Bentley
Larry Webster

After 25 miles of cruising south on Highway 1, the silky Bentley sputtered and then, as it is known in the British vernacular, “failed to proceed.” Wilke deftly slid his spotless car onto a dirt cutoff. We guessed at the culprit—fuel delivery—and had a look under the hood. The mechanicals of these vintage machines are relatively simple, but we feared soiling the recently detailed engine bay, so we skipped attempting a fix. Instead, we called Hagerty roadside assistance.

In the meantime, Wilke’s personal mechanic, who was on hand to monitor the freshly restored Bentley, pulled up next to us. He loosened a fitting that connected the fuel line to a carburetor and ran the electronic fuel pump based on the hypothesis that there was a blockage or air bubble in the fuel line. After reconnecting the line, the car ran perfectly.

We wafted back up the coast and on Sunday, Wilke’s heirloom Bentley took second place. He later said, “I could never have imagined driving up to the podium to accept a prize and it was one of the most amazing experiences I’ve ever had.” And also, an amazing finish for a Pebble first-timer.




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