The call, when it came, inspired goose bumps of joy. How would I like to help the fine folks at Bentley Motors reenact the epic and absurdly sybaritic jaunt that their founder, W.O. Bentley, chairman Capt. Woolf Barnato, and the rest of the Bentley Boys — a pack of wild playboys, pilots, and industrialists — took in the 1920s and in 1930 from the Bentley factory outside London all the way to France’s Loire Valley and back again? The destination: the 24 Hours of Le Mans endurance race, the most prestigious and grueling event of its kind, which celebrated its 90th anniversary in June. Back in their day, those ne’er-do-well bon vivants drove their racecars all the way to Le Mans, raced around the clock, then drove home again — and managed to win the competition four years in a row, from 1927 through 1930. My proposed journey was simpler: Drive a 2014 Bentley Continental GT Speed Convertible in a seven-car road rally. The point: to celebrate all of Bentley’s wins, including the 10th anniversary of the marque’s last outright win, in 2003; enjoy some of the finest automotive engineering on the planet; hang with two (yes, two) charming Le Mans-winning drivers, Derek Bell (five-time winner) and Guy Smith (literally the “guy” first over the finish line in 2003); and experience a lap around the iconic 8½-mile road course. My immediate response: “When do we leave?”
The world is awash in well-intentioned “bucket lists” that recommend tours so thoroughly planned and executed that the best part, that elusive elixir called spontaneous adventure, gets plotted away. Those Bentley Boys knew better than anyone how to take a proper, old-school lark of a journey through gorgeous lands doing ridiculous and sublime things in powerful cars. The wine, women, and general mayhem they also enjoyed along the way were as important to the cause as the race itself.
And so it was that I found myself feeling a particularly delicious sense of anticipation as I checked into the swish Belgraves Hotel in London. A luxury hotel was an appropriate starting point for our retro journey, given that the Bentley Boys had a fondness for luxury London hotels as well. Immediately after their victory in 1927, for example, they headed straight for the Savoy, where they rolled their winning and still-grimy car into the dining room and ate around it in black tie.
Our 2013 edition of the Bentley Boys — several execs from the factory, Bell and Smith, and a handful of lucky journalists, including me — congregated that evening for dinner. There was enough laughter and alcohol flowing to make old W.O. Bentley and his pack proud. Smith, the driver who brought the prototype Bentley Speed 8 into first place 10 years ago and who has been testing Bentley’s new GT3 racer in preparation for the marque’s return to the sport in 2014, wound up the crowd with hilarious stories of some of the less glamorous realities of driving in an endurance race.
The next morning the official road trip began. I walked out to the curb and admired the view: seven Bentley Continental Speeds in various shades and guises (a coupe, a convertible, and a limited-edition Le Mans series). What do you call a group of Bentleys? A pack? A gaggle? No, I say it’s a pride, for that’s what I felt looking at the lineup — and at decals of my name and country flag on both front quarter panels of my assigned Silverlake blue convertible steed. My co-driver was a boisterous blond Canadian writer, Alexandra; we quickly embraced our moniker, the Bentley Broads.
We were off and running promptly at 8 a.m., parading through the streets of London and causing whiplash and phone photos at every turn. From the moment I stepped into the beautiful beast, I felt as if I were cocooned inside an Hermès Birkin bag: engine-turned instrument panels as pretty as fine jewelry, and soft, expensive-smelling pelts wrapped around a core of adrenaline. My ideal luxury good.
Time flew, and so did we. Before we knew it, we were in the port town of Folkestone, queueing up for our Chunnel experience. After easing our wide-bodied babies into the narrow train compartment, we climbed out and stood alongside them during the unglamorous 30-minute journey under the Channel. I tried to wrap my mind around what the same transit on a ferry must have been like in the 1920s.
The British passion for cars and racing knows no bounds — 100,000 people journeyed from England to France this year for the race — as was proved by the sudden appearance of a teenage boy in our train compartment. He stood, a look of bliss and awe on his face, as we chatted with Bell and Smith about what it’s like to be a Le Mans driver. “The mileage of Le Mans is equivalent to what a Grand Prix car does in a whole season,” Smith explained. “It’s like the Super Bowl,” agreed Bell. “You work for a whole year to prepare to be at your peak for 24 hours.”
To their point, there is nothing remotely normal about the 24 Hours of Le Mans. There are numerous classes of racers, from sports cars like race-prepped Porsche 911s all the way up to purpose-built prototypes. That means that the track is awash with vehicles all going at very different rates. At night, the constant passing dance gets a lot more exciting, with headlights flaring. Each team is composed of three drivers, who take turns for hours at a time behind the wheel while their teammates refresh. The fastest cars have been known to cover as much as 3,360 miles in one 24-hour period, with an average speed as high as 150 mph. So drivers have to be equipped with physical and mental stamina, laser focus, and nerves of titanium.
That conversation put us all in the mood to put pedal to the metal when we were sprung from the train in Calais to tackle the remaining six-hour drive ahead. As we raced south toward the Loire Valley, the landscape grew greener and the architecture began to age. Before we knew it, stone-façaded chateaus were crowning every vista, vineyards sprawling at their feet.
By dinnertime we arrived outside the town of Le Mans and slowed to a crawl as we trekked deeper into the area’s verdant woods. A nondescript dirt road led us to our home for the next couple of days: Two chateaus — one a stone masterpiece from 1553 and the other, adjacent, a more willowy version from the early 1800s. As ritzy as it sounds, it is a Le Mans tradition — for teams and loyal fans — to stay in such villas; hotels are few and far between.
The next day came too soon (thanks to more Bentley Boys-style shenanigans back at the chateau afterward). Driving into the official Circuit de la Sarthe at 10 a.m., along with hundreds of thousands of fans, underlined the importance of the event to me. And being two women in a Bentley convertible with their names on the sides blasting “Get Lucky” (hey, it’s a song about staying up till the sun, which we were about to do) got us some attention — and roses, handed to me through the driver’s window as we inched by.
Although the race was scheduled to start at 3, another much more important event was set for precisely 12:52 p.m.: three cars were allowed onto the track (a highly unusual honor rarely granted by the FIA, the governing board of the race). Those cars were Smith’s GT Speed in front; a screaming- yellow Continental GTC V8, driven by Mike Sayer (a young Bentley engine engineer turned PR exec) with Alexandra and me as his sidekicks; and Bell bringing up the rear in another GT Speed. The flaggers gave us the go, and we were off.
Being a car geek myself, I have journeyed to Le Mans more than a few times in my career. I have always watched the cars, brake disks glowing red in the night, streaking past me and under the historic tire-like arch of the Dunlop Bridge. I have always dreamed about being in one myself. And here I was, looking up at the underbelly of that famous overpass. I could hardly suppress myself as we catapulted down the Mulsanne Straight. I couldn’t believe how long it felt, even at 160 mph, and shuddered to imagine driving it in the dark in rocketing traffic.
Our lap ended all too soon. The rush, however, hung about us through the afternoon as we watched the real racers battle it out, the screams of various engines piercing the air and our very ears — the eerie, futuristic whir of the Audi diesel hybrid prototypes; the baritone boom of the Corvette and SRT Viper GTS-Rs; the high-pitched, shrill notes of the Ferraris. Toward nightfall, intermittent rain showers deluged us. As much as I fantasized about being one of those brave racers, I was suddenly happy for the welcoming hospitality options up and down “Main Street” — the collection of commercial boutiques, food stands, and trinket shops constructed to offer fans respite through the night.
Because Bentley is owned by Volkswagen Group, which also owns Audi (and Porsche and Lamborghini and VW, among others), we were given VIP access to Audi’s over-the-top hospitality “rest stops” strategically placed around the track. But no amount of sumptuous catering can take away the gnawing fatigue that set in as the cold did, at about 3 a.m. With that sleepiness also came guilt: How dare I feel exhausted when extreme athletes were out there tirelessly risking life, limb, and expensive sheet metal?
I’d like to tell you we did the right thing, as our theme song suggested: Stay up all night. But the truth is, we returned to our chateau and slept for five hours, showered, ate, and then returned to the track. That whole time, those pilots were relentlessly watching speedometers hover well over 100 mph, lap after lap, after lap, after lap.
To no one’s surprise and our group’s delight, Audi won again this year with its hybrid R18 e-tron quattro. From an observation deck high above the start-finish, we watched the masses swarm the track and the winner’s podium. It was awe-inspiring, but then again, we already had another inspiring event on our minds. As in our Bentley-esque sprint back to the U.K. in the morning.
As we revved our W12 engines along France’s A28 highway, the road was swarmed with remnants of the U.K.’s colorful automotive past: Morgans and Caterhams, Nobles and Triumphs. Our pride of Bentleys wove between and around them, completing a visual testament to England’s automotive ingenuity and weakness for tinkering all at once.
I would tell you that it ended all too soon, but that would be a cliché. In fact, the trip gave me a whole new way to look at passions, travel, and life. Every day should be lived with abandon, speed, and the finest luxuries you can afford. It’s how W.O. and his band of racing brothers lived — to the limit and beyond. Which explains a little-known fact: When Ian Fleming first created James Bond, 007 did not drive an Aston Martin at the outset — he drove a Bentley. And now I fully understand why.
If you go
Here’s how to experience the spectacle of this seminal race in person.
Where to stay
All the teams and many fans in the know rent chateaus — grand and petite — in the Central Loire Valley during race week. Several sites offer a range of places and prices. The best are homeaway.com (search “Loire” and/or “Sarthe”), vrbo.com (search “Central Loire Valley”), and holidaylettings.co.uk (search “Le Mans”).
Where to eat
One of the many benefits of the Loire Valley is the spate of Michelin-rated dining experiences. See all options at viamichelin.com, or try two particularly excellent spots:
La Botte d’Asperges
49 rue Nationale
Le Grenier À Sel
26 place de l’Eperon
What to do
Bone up on race history at the excellent museum dedicated to the event:
MusÉe des 24 Heures — Circuit de la Sarthe
9 place Luigi Chinetti
For ticket information, schedules, and other pretrip advice, go to lemansrace.com.
This story is from the September 16, 2013 issue of Fortune.