When your time is short but your passions high, here's how to get intimate with a city.

Do the Spanish Steps in Rome lead to St. Peter's Basilica? Absolutely not! Pardon my yelling, but it's ten o'clock at night, I've been walking for two hours trying to find the most famous church in the world (one that's longer than two football fields), and instead I'm standing at the bottom of 135 marble steps in the opposite direction of where I thought I was headed and which lead to a different church entirely. I once crossed 20 miles of treeless, unmarked Saharan sand dunes, guided only by my compass and the sun, without getting lost. How then is it possible that in Rome, a city littered with famous landmarks, street signs, and 2.7 million people who could find their way to the Vatican blindfolded, I'm as turned around as Christopher Columbus when he said, "Funny, this doesn't look like India."

I'm here to speak at a business convention. I don't do much suit-and-tie traveling, but the other attendees tell me it's common at these events to be sequestered in the hotel grounds like a gang of ankle-bracelet-wearing white-collar criminals. Any free time is spent at the hotel golf course or poolside, sipping cocktails. Then, when the meetings conclude, you rush back home—without experiencing any local culture or history.

Personally, I don't do golf or tanning, and after 24 hours in which my only exposure to anything Italian is the room service pasta, I'm getting antsy. Fearing that I'll see Rome only from the window of my airport taxi, I ask myself, "What's the fastest way to get to know a city?"

Then it hits me: "Speed dating."

Hey, if an organized series of brief encounters can hook you up with a potential mate, then surely it can get you intimate with a city, too. I decide to take a day to speed-date Rome, seeing as much of it as humanly possible.

First tip: Hire a guide. There's no time to fumble with guidebooks.

9 a.m. I meet my guide, Letizia Ambrosi, near the Colosseum. She has agreed, for the next eight hours, to give me the CliffsNotes version of what would normally be three days of sightseeing. Appropriately, we're both wearing running shoes.

The Colosseum, according to Ambrosi, opened in A.D. 80 to a booming business. "Crowds of 50,000 to 60,000 came to watch battles matching gladiators, Christians, and lions," she tells me. I add: "And Russell Crowe, of course."

Please note that in speed dating sometimes the faces run together and the facts get muddled. But I'm fairly certain Ambrosi says the Colosseum eventually became a kind of Home Depot, where people helped themselves to building supplies—bricks, iron, and especially the marble that once covered the walls.