"When clients leave, I want them to leave with the most beautiful smile," Angelo is saying as we glide through the streets in one of the black Mercedes vans that his company, Access Italy, uses for its tours.
Angelo, who is 57 and looks like a twinkly, better-fed, benevolent version of Larry David, has just treated me and my 13-year-old daughter, Alice, to a behind-the-scenes tour of Il Campidoglio and Rome's city hall. We had been walking through the building, arguing about politics, when suddenly Angelo opened a nondescript little door and we stepped outside onto the building's rooftop. Dizzy from the height, we walked across the roof, gazing at the far hills of Rome and at something equally gratifying: a swarm of tourists far below us, undoubtedly being lectured about the political, social, and economic legacies of the fourth-century emperor Constantine I and worrying about whether they were going to miss the bus to the restaurant.
On the way out, we dropped in on the mayor himself, Gianni Alemanno, a small, courtly figure who ushered us onto his private balcony. "When I was here with Oprah, the mayor wasn't in," Angelo said, and I felt a prickle of pride—he was in for us! Angelo met Oprah about 15 years ago and has guided her in Italy three times, enough so that they now consider each other friends. "In the early '90s, my lawyer said to me, 'If you're going to Italy, I know the guy you should meet—he'll take good care of you," Oprah says. "And that's an understatement when it comes to Angelo. He seems to know everybody in the whole country." She is one of a number of notable clients, among them Diane Sawyer, Will and Jada Pinkett Smith, and Michael J. Fox. Not that Angelo recognized Fox. "I asked him, 'What do you do?' and he told me, 'I'm an actor,'" Angelo says. "I thought, 'He's a short guy with a backpack and jeans.' I wondered how this college kid had enough money to pay for me."
Still, the bulk of Angelo's business comes from regular people—regular being a relative term, since he charges an average of $500 a day. He has about 50 guides across Italy and matches the tour to the client. If you are an oenophile, you might go to the Badia a Passignano winery, an estate that dates back to the year 395 (and where it is rumored Galileo once taught math). You could study the work of Caravaggio, or visit an olive farm, or sail down the Amalfi coast. Or you could simply waddle from restaurant to restaurant, blissed-out on pasta.
He gets all kinds, Angelo says—from hard-core fact-seekers to rank amateurs who lose heart at Famous Building Number Two and clamor instead for Cup of Coffee Number Three. "After five minutes, I understand what they want to do," Angelo boasts. Many of his clients (90 percent of whom are American) want to go to un-touristy spots, and Angelo obliges. For example, he knows a man who has the key to a door off the Sistine Chapel. The door looks as if it would lead to an old storage area, but inside is a robing room for pontiffs—where a cardinal changes from his red robe into a fancy new white one after being elected pope. The vestments are waiting there, Angelo says, in three sizes: "one for a fat pope, one for a medium pope, and one for a skinny pope."
Angelo's favorite places in Rome