A 1936 Lancia Astura

The throaty roar of revving engines echoed off Monte Carlo’s famous casino and the neighboring Hotel de Paris as drivers prepared for the start of the Louis Vuitton Classic Serenissima Run last April. The brand, which celebrates travel, has sponsored seven of these elite classic rallies around the world since 1993. Christian Philippsen, who is in charge of the jury and car selection, reviewed more than 120 applications for the 42 slots, selecting only exceptional cars to create a jaw-dropping $300-million field that included William Evans’ 1913 Isotta Frachini IM, Arturo Keller’s 1938 Mercedes-Benz 500K (which was awarded the best of show prize), Bruce Meyer’s 1929 Bentley 4 ½ liter, Michael Leventhal’s 1950 Ferrari 166MM, and Thomas Price’s 1962 Ferrari 250 GTO, a car so rare that a similar model recently sold for more than $30 million.

Sports Director René Metge and his team planned a 1,400-kilometer (about 870 miles) scenic route through the Alps on the way to Venice with stops in Menthon-Saint-Bernard, France, Stresa, Italy, and Verona. Metzge, a three-time winner of the Paris-Dakar Rally has organized the Classics since the first race. “The starting and finish lines are the most important things to choose,” he explained during a garden party lunch at a private palazzo in Venice. “Once you have chosen them, everything else comes together. We organize rallies that are possible but not easy, and we select the cars according to the itinerary, which is why there are so many Ferraris this year.”

From the starting point in Monte Carlo, we embarked on a twisting and turning climb of long switchbacks through the Mercantour national park in southern France. After a quick buffet lunch at a snowy Napoleon’s Retreat, I joined Philippsen in his one-of-a-kind 1939 Alfa Romeo 6C 2500 SS “256.” Using the thick race book detailing turn-by-turn instructions, I relayed the directions as we talked. One wrong turn can take you miles off course, which may explain why Philippsen continually asked if I could see other competitors for reassurance.

Christian Philippsen’s 1939 Alfa Romeo 6C 2500 SS “256”

“These cars are like sculptures, they are truly art in motion,” he said as we descended the serpentine road from the restaurant. “Cars can feed the senses: You can look at them and see the shapes, proportions, and colors; you can touch them, smell them, and listen to the engines. If you buy a painting, you just put it on the wall and leave it there.” A steady rain began to fall as we closed in on Menthon-Saint-Bernard, France, on the shores of Lake Annency. After struggling to keep up, the old Alpha’s windshield wipers ultimately quit, leaving us to peer through the rivulets streaming down the glass. While wiping down the foggy windshield, Philippsen commented on the technological advancements that have been achieved in automotive design from improved windshield wipers and defrosting systems to antilock brakes and other safety features—seat belts immediately came to mind. Regrettably, though, we conceded that all the universal safety standards have resulted in rather bland cookie-cutter cars that hardly inspire the passion and admiration ignited by their charismatic ancestors. In village after village, passersby would stop, point, and smile when we passed through.

Another aspect of the course planning involves selecting special experiential stops along the way. Our route included private lunches at the Rouvinez winery in Switzerland and at a private castle in Italy. We also toured Louis Vuitton’s shoe factory in Fiesso d’Artico near Venice. Philippsen added that another consideration in choosing participants is the social aspect of the rally, so participants are often friends from around the world who have participated in previous events.

Winners for each class were awarded trophies at the final gala on Venice’s Piazza San Giorgio overlooking the Grand Canal. The event’s grand prize was awarded to a 1923 Bugatti Type 23 piloted by Giuseppe Radaeli and his son.

John and Tamsin Bentley of England piloted an open 1932 Alpha Romeo 8C 2300, weathering the elements with aplomb. “That first day we started in the sun, went right up into the snow, and came down to an English summer—pouring rain,” she said, clearly relishing the adventure. “The course was challenging,” added John. “We were doing 11- to 12-hour days, but we had the right car for it. The guys with large, heavy cars had quite a work out in the mountains.” The Bentleys were awarded the Moët & Chandon Sparkle award for their exuberance throughout the race.

“At times, we could drive quickly and at other times we were doing hairpin turns at under 10 miles an hour,” said Jack Thomas of St. Louis, who raced with this wife Debbie in a 1955 Ferrari 375 America. “Each day brought a new vista and a great experience. The roads were wonderful to drive and challenging at times. Having completed it, we all have a sense of accomplishment.”

1955 Ferrari 375 America

William “Chip” Connor II of Hong Kong, who took the prize for the Track & Road class, drove a 1961 Aston Martin DB4 GT with his wife Jacque. “The Dolomites were spectacular,” he said. “But, the one photograph I wish I had taken was of Evert Louwman’s Mercedes special roadster 500K, Tom Price’s GTO, and Michael Leventhal’s Ferrari 166 Mille Miglia all in a row in front of gas pumps at a station in Italy.”

Of course, antique cars have a propensity to break down, especially when being pushed hundred of miles through the mountains. But each day’s trials and triumphs were the subject of entertaining banter over cocktails and dinner in the evenings. The third leg from Stresa to Verona proved especially challenging for many of the drivers, some of whom did not arrive to display their cars on Piazza dei Signori until after 9 pm.

“I broke down on the third day on several occasions,” recalled Thomas at the awards ceremony. After his car quit in a construction zone in Como, Thomas called on the event’s mechanics, who got him started again but warned him not to kill the engine for 100 miles. “We made a wrong turn in Riva del Garda, and the car ultimately conked out,” he continued. “We were a mile off route, and we speak no Italian, but we were rescued and befriended by several Italians, who got me into a local garage. Ultimately, we could not get it started, so we made our triumphant entry into Verona on the back of the flatbed.” He and the mechanics worked all night to get the car running for the final leg. “If Louis Vuitton is about the spirit of travel and adventure,” he added. “We certainly experienced it.”