On the shores of Lake Como in mid-May, the Concorso d'Eleganza Villa d'Este gathered its usual procession of priceless machinery and outsized personalities. It is the rare concours with a watchmaker woven into its fabric: A. Lange & Söhne has been a partner since 2012, presenting a one-off timepiece to the Best of Show winner each year. Small wonder the watches circulating the lawn rewarded as close a look as the cars.

While the classics and the big personalities make the headlines at the world's top concours, the more personal stories tend to come from the wrist. Sometimes it is about winning, Rolex Daytonas earned in the heat of battle. But a watch can carry something more private, a tiny mechanical signifier marking everything from a hard-won achievement to one of life's most unforgettable milestones.

Earlier in the season, back in March, the Amelia Island Concours d'Elegance drew the same world to the Florida coast. Founded three decades ago by collector and automotive journalist Bill Warner, Amelia has long been the cozier, insidery counterpoint to pinkies-out affairs like Pebble Beach and Villa d'Este, with the same loyal cadre of collectors and motorsports figures, the auction houses that trail them, and the crowds flooding the greens at the Ritz-Carlton Amelia Island.

At both, we caught up with the people who orbit this world, race drivers, collectors, curators, and every shade of main character in between, to find out what the watches on their wrists actually mean to them.

Dario Franchitti is the proud owner of a particular Rolex Daytona, the one he earned for his team's overall win at the 2008 Daytona 24. However, the flying Scot was sporting a Daytona he acquired for a very different reason. "In 1997 I was on my way to Vancouver for my rookie season in IndyCar," he recalled. When he asked to see the stainless Daytona in the case at the duty free he received the common, "We don't have that one" response. After working his charm on a manager, he became the proud owner of the coveted timepiece. The price? A mere £2,250 (which translated to around $3,600 at the time). Franchitti said he went through a heavy period of acquiring watches around 25 years ago, including various Rolexes, Breitling Navitimers, IWC Big Pilot Top Guns and the like, but that there's a special place in his heart for Daytonas.

Hagerty CEO and Chairman McKeel Hagerty's life work may be centered on furthering the classic automobile hobby, but his wrist candy reflects a more personal priority. Hagerty's Piaget Polo Perpetual was gifted from his wife Soon last summer to commemorate their 15th wedding anniversary. The 42mm white gold edition features a blue obsidian dial, an ultra-thin caliber and a counterintuitively sporty strap. "It's low profile and looks tough with a suit," he said, acknowledging the elegant utility of the sentimental keepsake.

"I'm hard on watches," four-time SCCA Trans-Am Series Champion Tommy Kendall said. "I always wore a watch while I raced, so I got in the habit and this is my workhorse." Kendall's workhorse du jour is an IWC Ingenieur Automatic Mission Earth, a solid hunk of a timepiece that looks rugged enough to survive the 11 consecutive Trans-Am races he won in 1997. Kendall remarked that during his first three championships he purchased Submariners and GMTs for his crew. When he and teammate Paul Newman won the GTS class at the 1995 24 Hours of Daytona, he expected to take home a Rolex Daytona. "I was really looking forward to that watch," he said, but didn't. A few months later in Miami he spotted a new Daytona on Newman's wrist. "I get it," Kendall said, "you're the reason everybody wants it and so forth."

Caroline Kendall described her mother-in-law Claire Kendall as "just a legend, a beautiful woman, and a really great person." The mother of Caroline's husband Tommy Kendall had a practice of asking her grandkids which of her pieces of jewelry they'd like, which led the elder Kendall to joke, "Well, I'll take the gold Rolex because it reminds me of when I met you in the 80s." In an act of ultimate affection, Claire gifted her daughter-in-law her coveted gold Rolex Datejust. "I am so honored that she gave it to me right before she died," Caroline said. "I always wear it when I have to go somewhere nice, and I wear it with pride. She died way too soon."

The self-described “resident car nerd at Pixar” doesn’t just apply his automotive knowledge to animated films. Jay Ward also judges numerous concourses throughout the car show calendar, including both The Amelia and Villa d’Este. His eclectic taste in timepieces was on display at both shows. At Fernandina Beach, he sported a Snoopy Mission to Earthphase Swatch Moonswatch on a rubber band in order to cope with the humid environment. “I also don’t want to wear a big chunky chronograph that could scratch a car while I’m judging; it’s nice and light on a hot day like this,” he said. A few months later he donned a more traditional Heuer Autavia on a rally strap at Lake Como, where he took a bit more care around the priceless cars.

As the Executive VP and Curator of Collections for the vaunted Revs Institute, Scott George is intimately acquainted with some of the most historically significant cars on earth. While he's no stranger to precious timepieces (he counts a Rolex, Chopard and Tourneau in his personal collection), his daily is a bit more workaday. "I bought this Citizen [Eco-Drive] at a Costco in 2017," he said, adding, "I wanted a mechanical activation and all that at an everyday price." Unlike his more valuable watches, "if I damage it I'm not going to feel too terrible about it." While acknowledging that the leather strap is ready for replacement, he said, "I'm loving this watch. It's never let me down in all these years."

Mailani DeYoung grew up apprenticing with her father as he restored countless Porsches, so it's no wonder she counts racer Justin Bell as her significant other. Bell presented her this TAG Heuer Carrera Chronosprint x Porsche for Christmas, a fitting gift as the special 911 Edition timepiece incorporates a party trick in which a red line demarcates the amount of time it took for the first Porsche 911 to reach 60 mph. "And then the mechanism slows down to catch up for a minute. So it's a terrible, accurate stopwatch," she joked, "but it's got a cool and complicated movement. Justin is a TAG Heuer ambassador so we have to represent," she told Crown & Caliber with a smile.

"It's actually a perfect story," jewelry guru Brooke Hyman said of the two-tone Rolex Datejust on her wrist. "In 2016 we were showing [a 1932 Duesenberg J-354 Victoria Coupe] here at Amelia and we won the Rolex Timeless Elegance award. We went across the ramp and they handed me the green box." Hyman modeled the Rolex along with jewelry of her design against father Mark Hyman's lavish 1952 Chrysler Ghia Styling Special one-off. The elder Hyman was wearing a Breitling SuperOcean Heritage. "I like these smaller ones I can wear with a dress shirt," the big guy said of the not inconsiderable 46mm wristwatch. "The big ones are too much."

Andy Reid considers friend and head of BMW Classic Tom Plucinsky the ultimate enabler. "It's his fault," he said, pointing to the gorgeous A. Lange & Söhne LANGE 1 on his wrist, reference 101.021**, with its champagne dial**. The two were at last year's Concorso d'Eleganza Villa d'Este when Plucinsky suggested the collector, consultant, and analyst acquire a piece from the event's watch partner. "I was going to buy a lesser Lange," Reid reflected, "but Tom said, 'you can buy the lesser Lange or you can buy the Rolex Daytona of Langes. You should buy that one.' He pushed me over the edge." The carpe diem spirit served double duty, as Reid justified purchasing the timepiece as a way to celebrate his 1957 Chrysler Super Dart 400 getting invited to participate in the 2025 Pebble Beach Concours d'Elegance.

Like many gearheads, Tom Plucinsky has a passion for cars that extends into watches. However, unlike the vast majority of enthusiasts Plucinsky dives deep into his horological hobby by servicing watches in his custom-created workshop. Plucinsky, who is the head of BMW Classic North America, has been a regular at the BMW-sponsored Concorso d'Eleganza Villa d'Este. The event has had A. Lange & Söhne as a partner since 2012, repeated exposure that eventually led Plucinsky to succumb to the watchmaker's complicated charms. He happened to also be wearing a LANGE 1 (like friend Andy Reid) at The Amelia, only a Time Zone 116.032 reference in pink gold with an opaline silver dial. "The LANGE 1 started the [A. Lange & Söhne] rebirth in 1994," Plucinsky said, "so it's the signature watch from the brand." One full circle moment came when he was showing his timepiece to a Lange watchmaker at Villa d'Este, and she recognized it as one she had assembled herself, a moving moment that reveals the artist's handiwork like a signature.

BMW Product and Technology Spokesperson Jay Hanson said his IWC Portugieser Chronograph came to him through unexpected circumstances. "Basically, I came into possession of a family heirloom that I had no real connection to, which turned out to be valuable." Without a sentimental attachment to the heirloom, he sold it and "rolled it over" into the Swiss timepiece. A longtime fan of the color blue, Hanson said the salesman recognized his color preference and suggested he take the cobalt-dialed watch outdoors to view in natural light. "He was smart," he laughed. "I said, OK, let's do this."

As flashy as his surname might sound, Markus Flasch’s Tissot Seastar 1000 is anything but. The ceramic-bezeled dive watch is fittingly rugged for the BMW Motorrad CEO, who enjoys riding company bikes en masse roundtrip from Munich to Lake Como. While this year’s trip down was hampered by unseasonal snow, the crew managed to ride back to BMW’s hometown on a variety of Beemers.

While many design bosses tend to embrace avant garde timepieces, BMW and Alpina VP Max Missoni opts for a more sentimental watch. “In Austria we have a Catholic tradition of getting a gift when we come of age,” he says, referring to the Omega Speedmaster he wears on a dressy leather strap. “It was given to me as a memento by my godfather,” he adds, suggesting that—at least in his mind, the memories the chronograph bears are stronger than any design statement.

Long before Trent Abbott purchased his Rolex "Bluesy" Submariner, the VP of Global Private Client Development at Hagerty said his first Sub was purchased "right out of college when I was a scuba instructor in Hawaii with no money. I had no business… I was eating bologna sandwiches every day." Abbott credited personal heroes like Nick Nolte in "The Deep" and "Jaws" author Peter Benchley, who was featured in a Rolex ad campaign, for creating the aspirational buzz that got him hooked on the brand. "My wife took mine several years ago and I never saw it again on my wrist," he added, "so I replaced it with a vintage Bluesy."

Fine artist Austen Segal's automotive painting complements sheetmetal with intricate, script-like patterns. Her eye for detail is naturally attuned to watches, a focus which caught her off-guard when she met with a client. "I saw the watch on his wrist and I absolutely fell in love with it," she recalled. "When I did my first show in LA and he wanted a painting, I said, 'trade me the watch for the painting.' And I've worn it every day since then." Segal said she's gone through about 14 bands and continues to enjoy wearing her IWC Portugieser Automatic 7 Days. Segal's appreciation of fine metalwork carries through to her line of intricately crafted purses, which are produced through her Fèhr design label.

Across both lawns an ocean apart, the same truths remained. The cars pull the cameras, but the watches are where the stories live, strapped close to the pulse, marking a win, a marriage, a mentor, a memory. Ask anyone at Villa d'Este or Amelia what is on their wrist, and you seldom get an answer about the watch. You get an answer about life.