Does switching sexes change your worldview—and the way the world views you? Jennifer Finney Boylan has looked at life from both sides now, and finds that gender has its privileges

We—my friend Curly and I—have had our photo taken with the gladiators, the ancient city glowing in the evening light all around us. The four gladiators are in fine spirits and have good-naturedly offered to stab Curly in the ribs and to cut off his head. But when the time arrives to provide them with "a little tip," things turn ugly. "Ten euros," says the head gladiator, whom I've dubbed Grappa Drunkus Maximus. "Each."

I point out that ten euros per gladiator is rather more than I had in mind. Grappa Drunkus Maximus does not take kindly to this observation, however, and within seconds all four men have drawn swords and are staggering toward us, muttering curses in Italian. The pleasant surprise—pleasant for me, that is, not so much for Curly—is that while I am the one who has refused to render the euros unto Caesar, it is Curly whom they've decided to kill. This is something that is no doubt covered in gladiator school—always murder the man—but it's news to me. The warriors brush me to one side, even though I am the source of all the trouble, and zero in on poor, defenseless Curly—whom, it must be added, didn't want to get his picture taken with the gladiators in the first place, fearing from the outset (correctly, as it turns out) that the whole business was just "some tourist rip-off."

As I watch Curly—pursued by the angry men in Roman armor—disappear, screaming, around the far curve of the Colosseum, I consider, not for the first time in Italy, how much things have changed since the last time I stood here, when my name was James and to all the world I appeared to be a man, even though I carried the crushing, secret melancholy of the transsexual. But now—hormones, surgery, and a generous supply of therapy later—I walk these ancient streets a woman. Even though the entire tedious business is now several years in the past, I still have the annoying tendency to look at the world, from grappa to gladiator, as if it is all brand spanking new, and to wax rhapsodic about it. "Can you believe it?" I say to my weary friends, their patience long since stretched past the breaking point. "The experiences of men and women are so different!"

Travel is colored by gender, of course, and the differences in the treatment and perceptions of male and female travelers are on my mind as I visit Venice—a city I'd last been to five years ago with my wife, Grace—and Rome, where I'd backpacked in the summer of 1976, a hippie boy with a gram of hash and hair almost its present length, although several shades darker and considerably less well-conditioned. I talk things over with that younger self as I revisit familiar sights. This dialogue isn't something unique to transgendered people, though. We all do it.