A good tour guide can change the way we experience a destination.

Credit: Illustrated by Brett Affrunti

Some travelers—you, perhaps—are averse to the very premise of a guided tour. No self-assumed sophisticate wants to be led around by someone holding a whistle and a Ping-Pong paddle with a number on it. I certainly never did, in my indie-traveler youth. Instead I relied on books, on my own wits, and on friends and local contacts, who’d point me to the underground galleries and unsung sites that I believed told the real story of a place. In hindsight, I was poring over footnotes and ignoring the main text.

This error first struck me on a visit to Varanasi, India. At the time I was still naive enough to think I knew everything, or that I could at least figure it out on my own. So I spent three days walking the banks of the Ganges, watching the most bewildering scenes drift by. The experience was undeniably visceral, yet ultimately unsatisfying—like a Hindi movie with the subtitles off. On my fourth morning I met a local professor at a teahouse who offered to show me around in exchange for lunch. We spent the afternoon retracing my earlier steps, with my guide explaining everything I’d missed: not just the what and the who, but the how and the why.

India, of course, begs for interpretation, which is why seasoned travelers will hire a guide in Varanasi or Delhi or Mumbai when they wouldn’t consider it in Rome or Paris or London. But even the latter cities come to new life—even after your umpteenth visit—when seen with a skilled guide. Indeed, some of my most memorable tours took me not to obscure or exotic sites but around places I’d considered familiar: the Tower of London, midtown Manhattan, the heart of ancient Rome. A good tour guide can bring you to those coveted under-the-radar spots, get you into private collections your friends have never seen. But a great tour guide can steer you back onto the beaten path and help you see the celebrated sites as if for the first time.

“People often tell me, ‘We’ve done the Pantheon—show us something new,’” says Frank Dabell, one of Rome’s top tour guides. “My response is, ‘Well, yes, but would you listen to your favorite piece of music only once?’”

Did you know that Rome’s Palatine Hill gave us the word palace? Were you aware that czar and kaiser both derive from Caesar? Did you know that when the Pantheon was completed, the surrounding piazza was 15 feet lower than it is today, so someone standing outside would have seen not a rectangular box topped with a dome but the implied outline of a perfect sphere?

Maybe you knew all that. I did not, until I spent an afternoon with Dabell. Raised in Rome by French and British parents, he attended Oxford University and studied at London’s Cortauld Institute of Art, and now teaches at Temple University’s Rome campus. In his spare time he leads walking tours, which ostensibly focus on art and architecture but touch on pretty much anything you can think of, from Italian politics to ancient plumbing.

Dabell wears bright-red socks, speaks with a charming British accent, and is madly in love with art, with storytelling, and with Rome itself. He’ll visit the Pantheon twice a day, just to watch the shifting play of sunlight on the interior walls. Every April 6, Raphael’s birthday, Dabell stops to lay a flower on the master’s tomb. He can gracefully recite both the original Latin and the English translation of the famous epigraph above it:

Living, great Nature fear’d he might outvie her works

And dying, fears herself may die.

“Raphael knew the pleasure of looking and thinking,” Dabell says. “Something that’s sorely lacking these days.”

We met through Casa Manni, a one-suite hotel located 200 yards from the Pantheon. Designed by Adam Tihany, the apartment is owned and run by olive oil maker Armando Manni, who opens his black book to connect guests with Rome insiders. Dabell is Casa Manni’s art expert. (He also freelances with Context Travel, which offers tours in a dozen cities around Europe and North America.)

We had only to walk within an eight-block radius of Casa Manni to explore one of the world’s finest open-air museums: the Pantheon, Piazza Navona, Piazza Colonna, the Trevi Fountain. Through the neighborhood runs a path, marked with inlays in the pavement, that forms a literal tourist trail. We were not charting unknown terrain. I had walked this route countless times myself and believed I had a decent understanding of Rome and its heritage. But Dabell proved me wrong. I hadn’t been looking and thinking.

Guiding may be the one instance where you generally don’t want a veteran professional. “People who are primarily experts in their subject usually make better guides than those for whom it’s a full-time job,” notes Maureen B. Fant, an American writer and Rome-based expat who coordinates tours for Casa Manni. After too long in the field, she notes, even the most inspired guides default to a tape loop.

Savvy tour leaders read their audience as well as they read the city, staying ever attuned to the ebb and flow of engagement. (The ideal candidate not only has a Ph.D. but also moonlights in an improv troupe.) Such skills are essential, since there is no such thing as a “typical” tour client, according to Fant: some are scholars themselves; others have barely cracked a guidebook. She recalls a couple who signed up for a tour of ancient Rome. The husband had no interest in art or museums, but happened to be in the bathroom-supply business: “He wound up asking a zillion questions about the fountains—how they worked, how water moved through the city. They became the basis of our walk.”

Standout guides also manage to transcend the job’s inherently awkward premise, which is to herd adults around like schoolchildren. In Dabell’s company, my wife and I felt less like two out-of-town rubes being led by a guide and more like three friends engrossed in conversation during a stroll across town. That conversation veered frequently from the topic at hand—to Libyan politics, New York City restaurants, the Beatles, pistachio ice cream. (A stop at Ciuri Ciuri, Dabell’s favorite gelato shop, proved a worthy detour.)

In the end it was the odd tangents and digressions that we remembered best. Dabell took as much delight in seeming asides as he drew from his primary subjects: seen through his eyes, a door hinge was as sublime as the Pantheon’s dome; a chipped tile remnant as compelling as any Caravaggio. Standing before Sansovino’s otherwise solemn sculpture of Mary, Jesus, and Saint Anne in the church of Sant’Agostino, Dabell directed our gaze to Anne’s fingers, which—now that he mentioned it—were subtly tickling the infant’s foot. “Such an intimate gesture, and so moving,” he murmured.

Who’d have thought we could spend 50 rapt minutes just circling Bernini’s Fontana dei Quattro Fiumi while Dabell pointed out hitherto unnoticed details? “Look at that palm tree, leaning in the breeze. Astonishing!” he swooned as we took in the fountain’s twisting, kinetic swells. “Water, light, sound, sculpture, architecture, theater—it’s the first complete artwork,” Dabell continued. “When this fountain was switched on in 1651, Bernini essentially invented the cinema.”

I figured I’d seen the best of Bernini over the years, but until Dabell brought me to it, I’d never encountered what is now among my favorite of his works: a haunting memorial bust of Giovanni Vigevano, a 17th-century gentleman, inside the church of Santa Maria Sopra Minerva. There’s nothing monumental about the likeness—rather an uncanny softness and vulnerability that belies the stone. “Bernini believed the best time to sculpt is just before the subject speaks or just after,” Dabell told us, and this was clearly the case with Vigevano. Bearded and frail with old age, he seems poised to utter a parting word; his head tilts almost imperceptibly forward, as if nodding in welcome to his own mourners. The bluish tint of the marble eerily suggests blood beneath skin, making the stone appear translucent. It is the most lifelike depiction of near-death I have ever seen. Yet there it was, virtually unnoticed by the throngs of passersby.

“Scholars know the Vigevano bust, but it’s not celebrated,” Dabell explained. “Encountering these busts of seventeenth-century characters no one’s ever heard of—it’s like meeting the people themselves.”

Seeing Rome on my own and then with Dabell was like the difference between scanning a piece of sheet music and hearing a choir sing it aloud. Suddenly the arc of the melody, the grace of the counterpoint, the thrust of the lyric all become clear. When I told Dabell this, he humbly demurred. “Sometimes you just have to step out of the way and let the art sing for itself,” he said as we gazed into Vigevano’s mournful eyes. “This is something we never make the time to do—just to stop, and look, without speaking.”

And so we did.

Casa Manni, 70 Via di Pietra, Rome; 39-06/9727-4787; casamanni.com; suite from $1,155. Frank Dabell is available through Casa Manni or Context Travel (215/240-4347; contexttravel.com; three-hour group tours from $90 per person).

For a list of our favorites, check out World’s Greatest Tour Guides.