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In return, he took me someplace that showcased his favorite Italian "art." Enoteca al Volto Calle Cavalli (rumored to be a favorite of Elton John's) is a rough-hewn ristorante tucked away on a winding street near the Rialto bridge. While the boyfriend adores "challenging" food and likes everything with ten kinds of sauce, I could live contentedly on protein bars, so I felt pretty adventurous letting the server choose what we should sample—salty creamed fish spread, tiny spicy langoustines, and pasta tossed in anchovy sauce. All delicious.

Cliché or not, we set off for a Bellini nightcap at Harry's Bar at the Hotel Cipriani. Who can resist a Hemingway haunt? I was tempted to snatch a signature ashtray—they are so bright and shiny, after all—but they’re less expensive than a drink, so we bought one instead.

By the time we got home from dinner, our bags had arrived, just in time for the drive to Florence. I was never so happy to see an inanimate object in my life.

I showered the suitcase—and the boyfriend—with kisses.

Friday: Finding Firenze

I'd pictured a scenic jaunt through the Italian countryside, with stops to tour lush vineyards and chat with ruddy-cheeked locals. I had forgotten to take into account the male need for speed. The boyfriend drove our tiny rental car in excess of 130 kilometers an hour on the windy Autostrassa while I, the girl with no sense of direction whatsoever, attempted to figure out if that town we just passed was anywhere on the map I was reading. In Italian.

Missing the exit into Florence—and dealing with the boyfriend's reproach—blew the last wisps of my romantic Venetian cloud away. And once we entered the city, the next hurdle was where to stay, since we hadn't made hotel reservations. Miraculously, one of the places I'd found on the Internet was actually close to a street I'd been able to find on the map. "Let's just go here," I said, jabbing it with my finger.

"Here" ended up being the Una Hotel Vittoria on the Via Pisana. Bright, shiny, and oh-so-postmodern, it was just the thing to get me out of my navigating funk. A giant floral mosaic spiraled through the lobby, echoed by a huge plush red couch in the bar. Our room was like a sexy little stage set, with tiny, dimmable twinkling lights surrounding the bed, and, behind a wall of translucent glass, a huge tile shower—a lavish, overgrown fish tank for exhibitionists. Best of all, when we walked in off the street, we paid much less than the going rate, due to vacancies.

As far as I was concerned, this was the coolest place in town. But we were in Florence, after all, so bright and early the next morning we queued up to see the most famous penis in the world, on Michelangelo's David.

If Venice is a courtesan turned semi-respectable countess, Florence is a prim dowager who supports the arts and goes to bed early, so marble nudes are about it for racy fun. Unless, of course, your favorite deadly sin is gluttony. Everyone I know who's been to Florence has told me to dine at Il Latini on the Via Palchetti.