Family Resemblance: Tracing The Lineage Of The Porsche 911

"We need some music. It's too quiet in here."

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Andreas Preuninger, head of GT development for Porsche, is sitting shotgun in an Amethyst Metallic Porsche 911 Cabriolet (964 edition) somewhere south of San Francisco. He connects his iPhone to the cabrio's retro navigation system and scrolls through his music library. "What sounds good to you? I have Green Day. Kid Rock. Metallica?"

And that's how I found myself blasting "American Idiot" while slicing through coastal California's winding roads en route to Monterey, California. But it does raise the question: Why on earth am I driving a purple Porsche with Andreas Preuninger in the first place?

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It all begins—and ends—with the iconic Porsche 911. Since the 911's introduction in 1963, Porsche has built more than 1 million of them. To commemorate this milestone, seven models spanning all generations have traveled from the Porsche museum in Stuttgart to California. The ultimate destination from here is Monterey Car Week, where the 911s will first be featured at Werks Reunion and then take to the track at Mazda Raceway Laguna Seca for some celebratory parade laps.

The plan seems simple and straightforward: A collection of automotive journalists and Porsche executives will caravan from our hotel in St. Helena to Monterey along a route that winds through some of the most scenic roadways along the coast before plunging inland. Along the way we'll swap cars at designated points so that we can experience every generation of 911.

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First up for me: a 1970 911S Targa furnished in a stunning Gemini Blue Metallic. A tiny surprise greets me when I open the frunk to deposit my modest baggage. The opening is a far cry from the commodious cargo areas of modern 911s: small, shallow, and nowhere near big enough for my duffel. Into the front seat it goes. With 180 hp on tap from a 2.2-liter flat-six, the 2,400-pound Targa has plenty of power to headline this group. I congratulate myself on my impressive lead until I realize the cars behind me are keeping their distance on purpose. She's a dirty girl; when downshifted and floored, the Targa emits a dank puff of smoke from the tailpipe. Anyone behind the Targa finds his or her recirc button in a hurry. It's easy to forget all cars used to be like this.

Of all the 911s, this one probably took the most getting used to. Pedals are narrowly spaced, and I adjust my feet to approximate a nimble heel-toe, with mixed results. The footwork shines in comparison to my shifting skills, however. Its five-speed manual is arranged in a dogleg position, meaning first is down and to the left, a fact that I keep repeating out loud so that I don't forget. Although the shifter slides easily from gate to gate, the detents are vague. I concentrate on not conflating second gear for reverse. And as sleek as the enduring shape is, the seating position feels a lot higher than in a modern 911. Thank goodness for the removable roof.