I spent my Sunday riding shotgun in a one-of-800 Ferrari in part of a million dollar convoy of the finest vintage sports cars money can buy. Here's how I did it.

Before I go on, I would like to thank Santo and Frank Spadaro, and everyone else at this drive. They were warm, kind, and welcoming in a way that extended way past letting me try and not drool over the leather interiors of their cars. They are good people.


In fact, the whole thing starts with Frank and Santo. They're the two guys who shaved my head back in June when we needed real Ferrari mechanics to handle a Ferrari-branded hair clipper. I connected with them through Mike Spinelli, Jalopnik's founder who also does work over at DRIVE now.

It turns out that Frank and Santo had worked on my friend Bradley's Ferrari 208 GT4. You know him as the guy who turned a passion for old cars into a watch company. That's the foundation that got me to this beautiful Sunday.

So it was Bradley who tipped me off to this drive. He had an extra space in his car, and all I had to bring was fifty bucks to cover the entry registration, lunch, and donuts along the way. It all went to charity and man was it worth it.

I met Bradley with another car blogger Drew, who runs the excellent MotoringConBrio, and we set off from Manhattan up to Westchester. We left at 7.30 and were one of the first to arrive at the host's estate.

The cars were unbelievable. Porsche 911s and 356s, Alfa Spyders and a Giulietta, an Aston Martin DB3, an Arnolt-Bristol (below), a Callaway Alfa Romeo GTV6 and maybe 20 more cars.

The star of the show, at least for me, was the 246 Dino, Ferrari's first midengined road car and one of Pininfarina's prettiest designs.


Before we left, the organizers sent every person who didn't have a car to ride in over to one corner, and all the drivers with empty seats went over there, too. Even if you didn't own some gorgeous vintage sports tourer, you could still go along for the ride.

Beyond that, nobody sneered at Drew's E36 M3. Another guy at the drive brought his stock '96 Impala SS. I'd gone to an event just like this a few months back and somebody turned up with a four-door E30 and everyone took that driver in as well.

If you're a good guy and you've got any kind of youngtimer car, like an old BMW or a Miata, you won't get turned away from an event like this.

Not that it hurts to have an Aston.

We all set off an organized route with instructions. It was clear and dry, with long winding sections outlining lakes to tight, up- and downhill sections where there was hardly a breath between one corner and the next.

The Dino 208 GT4 wasn't the happiest car in the slowest parts of the drive, but it ate up the longer bends. Beyond that, the sound made by that de-bored 2.0 liter V8 (the smallest V8 ever put in a production car, a way to dodge Italian tax codes) was absolutely glorious. It's not a fast car so we never were even fighting the urge to speed, but the Ferrari was amazing nonetheless.

Everyone met up at a farm stand, we had donuts and cider. It was like a councours d'elegance in the dirt lot.

I took many more shots of the red Dino and we were off again.

Sadly, even Ferraris get stuck behind minivans. The second half of the drive was not quite as exciting as the first.

When you're in a line of five classic fifties and sixties sports cars, though, you take in the view.

Also, the burning oil. That 246 Dino puffed blue smoke like a two-stroke. Frank and Santo proudly asserted that for old Italian sports cars, that's not a problem.

Drew in his E36 M3 was beaming the whole time. His photos, too, were absolutely fantastic (you can see a few here) and make mine look like I was shooting with a potato.

The drive ended at a diner near our starting point, we sat around and watched the Austin F1 race with everyone, including Larry Kosilla of Drive Clean, who had tagged along in a souped-up Lotus Elise. Cool dude.

Bradley and I were some of the last to leave and we practically got a private photo shoot with the Frank and Santo's late father's Ferrari 330 and that beautiful, beautiful Lancia Fulvia sedan.

I was starting to like the 330 more than the 246 Dino.

We left to drop off the 208 GT4 at Bradley's out-of-the-city garage and made it back to Manhattan in his other car, a trustworthy Alfa GTV6.

If there's any lesson, it's make connections. Find the garages with nice mechanics and fantastic cars, get to know the guys there, meet the owners, and you'll be on your way. Find somebody who knows somebody who knows somebody if it will get you introduced. Hang around and sweep the floors if it keeps you connected.

When you finally get your foot in the door you'll find that the people who work on classic cars are some of the best people you'll meet. If the car owners are anything like the people I rode with on Sunday, they'll be free from ‘yes I'm rich and I know it' pretentiousness and will welcome you into their club.

Beyond that, go out and drive. Even if you're not in a group of vintage Italian sports cars, beautiful roads are out there. Enjoy them.

Photo Credits: Raphael Orlove/Jalopnik