The Mille Miglia is the ultimate vintage car event, and a Ferrari is the ultimate car to drive in it. Which Ferrari to pilot, however, depends on your checkbook and tolerance for pain.

First, ask yourself if you want to be dry, relatively warm and comfortable, or if you want to go fast, be wet, cold and dazzle the crowds.

My “luxury” choice would be any of the 250 coupes or Berlinettas that qualify for acceptance.

The best 250 TdF will cost over $1m today, and a properly sorted one (i.e., not Rodeo-Drive puffed but road-race ready) will offer prodigious power, light weight, nimble steering, adequate brakes and predictable handling wrapped in a package that represents landmark styling. A TdF is one of those friendly race cars that makes a bad driver look good.

If your budget is a little more modest, for $150,000 a 250 Boano with period race history has nearly everything that the TdF does, except for the styling. Under the skin, a Boano and a TdF are really the same. And, with the magic of today’s technology, a good mechanic can make a Boano go faster than its creators ever dreamed it could.

By comparison, masochists can choose a very early 166, 195, 212 or 225 coupe, any of which will immerse the driver in total automotive agony. For starters, you get inadequate brakes, a recalcitrant and noisy gearbox, a weak differential and gearing best suited for a garden tractor. Add a hamster-sized powerplant, extraordinary oil consumption and seats crafted for a deformed Italian midget, and you’ve got the total picture.

The primitive coupes do have a roof, windows that will keep out some rain, defrosters guaranteed to drive you mad and token wipers usable until moisture appears. Your car will always be surrounded by fawning Italians while you are stopped by the side of the road, hood-up, desperately trying to locate that strange whining or grinding sound or find the source of all the oil and water that is leaking onto the rich, Italian soil.

If you opt for an early open car, get ready for a stylish but slow boat ride. You’ll find yourself in the rain, dripping wet, freezing and sloshing in a leaky but very expensive (and soon to be rusting) Italian bath tub, all while fighting off terminal exhaustion with fading headlights.

The ultimate car for the MM is a 250 TR. Driving one requires only chutzpah and an unlimited checkbook. They are blindingly fast, so you can get through the rainstorm a little faster. And the heat coming off the engine will keep your toes warm even if your nose, cheeks and fingertips are freezing.

I drove the MM in 250 TR S/N 0732, white with a blue stripe. On a rare warm and sunny afternoon, the Italian crowds went mad at the sight of our pontoon-fendered Testarossa. In the towns, the teeming masses parted as if I were Caesar entering Rome, returning victorious from protecting the Empire.

Hearing Italians of all ages shout, “bella macchina” as you speed by, engine shrieking at 8,000 rpm, is an experience that simply can’t be replicated. Suddenly, you forget about all the discomforts and revel in the extraordinary experience of driving a legendary race car on the very roads it was born to compete on.

More Articles

A Princely Collection of Rotting Cars

Imagine seeing hundreds of high-end Ferraris, Lamborghinis and McLarens—many with hardly any miles on the odometer—rotting away in tropical heat and humidity. While much has been written of the Sultan of Brunei’s car […]


When Japan Ruled the World

It doesn’t take a Harvard MBA to see that the Ferrari market is booming again. But I suggest this time is different from earlier booms and busts. A little history: In Italy in […]


1031 Tax trades revisited

As every Baby-Boomer knows, time is no longer our friend As the baby-boomers leave the market, many long-term-ownership collector cars are coming to the market. Some are sold because they sat unused for […]


Importing an F50: Part II

In the last issue of Sports Car Market, we reviewed the byzantine process of importing a Ferrari F50, S/N 103496, which had been converted to racing specs and was last year’s winner of […]


Ferrari: The Factory GT Racers

Schumie and the Formula One guys might get all the attention, but in fact Ferrari has been involved in GT racing for decades. From Group 4 Daytonas to the new 575 GTCs, Maranello […]


No Speculators

When I began trading Ferraris in the early 1970s, there were two types of buyers: flashy young men who made lots of money and thought the cars were “cool,” and engineers in their […]