NYC: Private Classic Car Midtown Tour & 1920s Guide

4.83

(133 reviews)

What’s the experience like?

I nearly tripped over my own feet trying to climb into the back of this glossy old Ford—honestly, I didn’t expect the step up to be so high. Our driver, Eddie, just grinned from under his newsboy cap and said, “You get used to it after a few rides.” He had the jazz already playing low on the radio, something brassy and bright that made Park Avenue feel less like a business district and more like an old movie set. The city outside was doing its usual thing—taxis honking, someone yelling about bagels—but inside that car it felt like we’d slipped through a crack in time.

Eddie told stories as we rolled past Central Park’s southern edge—about horse-drawn carriages and how Columbus Circle used to be way less chaotic. I remember the faint smell of leather from the seats mixing with whatever cologne he wore (something spicy, maybe cloves?). When we stopped at Bryant Park, he pointed out where people used to ice skate before the park got its facelift in the 1930s. I tried to picture it but mostly just noticed how everyone seemed in a hurry except us. There was this weird comfort in moving slow through Midtown for once.

We drove by Grand Central Terminal’s tunnels—I still can’t believe how many miles of books are hidden under the New York Public Library. Eddie quizzed us on it (I guessed way too low). At Times Square, he laughed when I tried to imagine what it looked like before all the neon—“Just squint,” he said, “and you’ll see it.” The Flatiron Building really does look like a slice of pizza if you catch it from the right angle. Never noticed that before.