Colleen Bell and Gwen McCaw, one of the four event planners dressed in Swinging Sixties with their 1967 Jaguar E-type
Colleen Bell and Gwen McCaw, one of the four event planners dressed in Swinging Sixties with their 1967 Jaguar E-type

The first day, Le Bon is out early taking the car for a test drive. She wears her hair in a low chignon with a green English-rose-print chiffon dress and T-strap heels. The car is borrowed from Majno, and as we sputter out of the driveway, Le Bon is bessoted; I am terrified.

Unlike the other women, neither Le Bon nor her husband. Simon Le Bon, collects cars. “I’ve always, always loved classic cars,” she says. “Up in my room I have a Formula One magazine and two classic-car magazine. I always have them with me. When I was younger and doing all the show in Paris and Milan, all the other girls would make fun of me because I would show up to hair and makeup with my Formula One mags!”

Barreling down the squiggling Tuscan road, the Bugatti sens out a constant stream of backfires, banging and popping like fireworks. The hole in the floor that serves as the gearshift rattles uneasily and, on a particularly curly, steep stretch, slips straight out of gear, refusing to be put back in places. Le Bon calmly stares straight ahead, jiggling the gear stick in an effort to shift into neutral to get to second.

“Come on, old girl! Come on!” The brakes squeal like Parisian gendarme sirens, while the honk of the horn is a noble, baritone hiccup.

On one narrow swath we come perilously close to a large man on a small bicycle, while a weary shepherd and his flock almost cause us to screech sideways. We drive past armies of grapevines that march down the sloping hills like strict rows of soldiers and groves of olive trees that glimmer silver as they fly past.

At every village we are greeted by either waves or dumbfounded stares outside roadside trattorias a ruddy shade of cantaloupe, the typical Tuscan orange.

Commanding the oldest car of the group, Le Bon lets everyone else leave ahead of us: “We never pass 50 mph, but Brenda Sullivan, the Pebble Beach–base wife of NASCAR champion Danny Sullivan, floors it past 120 mph in her 1973 Porsche Carrera.”

Lunch one afternoon is served at the hilltop Palazzo Collazzi, were pockets of conversation from the half-dozen linen covered tables float into the rafters. “Isn’t this much better than going to a spa and not eating?” ask Gwen McCaw, who lives in Seattle with her husband, telecom entrepreneur John McCaw, as she slices into her veal medallion. “That’s what you’d usually do with your girlfriends, right? Usually you’re driving from point A to point B in a minivan with four screaming kids in the back. To actually be in a car just to drive can be really relaxing and meditative.”

After lunch, over the din of our backfiring Bugatti, I tell Le Bon what McCaw had said at lunch. “That’s what I love about classic-car collectors; they all really seek out the joys in life,” she says, smiling. “It’s about the journey–that’s the thing.”

© Chloe Malle @ Vogue Magazine December 2011

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