Picture Studio 54 in its heyday, and you'll have a sense of the effort and enthusiasm required to get into this rustic Tuscan ristorante. The waitstaff plied us with complimentary glasses of wine while we waited in the alley outside and tried to keep other sneaky tourists from cutting in line. Finally, a bunch of business-tripping Gucci executives swept us in with their party, and we were seated for one of the most lavish meals of my life.

It's family style, so we got a giant jug of red wine to share with our new favorite strangers. Then came the antipasti of local liver spread—the boyfriend dived in immediately—and bruschetta and cold cuts. Next came pasta with red or white sauce; a main dish of rabbit, chicken, or beef; and sparkling wine and biscotti to finish. It was a minor miracle we managed to drag our drunken, satiated selves across the cobblestone bridge to our hotel.

The next morning, five pounds heavier but with light hearts, we set off for one of my favorite Italian attractions: the Prada outlet in Montevarchi.

It's not clearly marked, but any local can point you toward the unassuming warehouse. Inside is a treasure trove of past collections from Prada, Miu Miu, Helmut Lang, and more, all a whole lot cheaper than retail price. I tried on an armload of dresses and sweaters before settling on a very Audrey Hepburn gray wool A-line shift with a fur-trimmed hem for the (relatively) inexpensive price of $400. I also nabbed a pair of electric-green suede Miu Miu boots for the boyfriend for around $100.

Having dallied a bit too long in the shoe racks, we'd fallen behind schedule to get to Rome. We were hurtling through Umbria when we realized we were lost again. Neither of us wanted a reprise of the tension we'd felt on our way into Florence, so we both stayed quiet, still flying along. Then the crumbling tower of a monastery appeared on the horizon.

"Let’s check that out," said the boyfriend. A sucker for adventure, I agreed, and we pulled off the road. What looked like a scenic ruin was in fact La Badia di Orvieto, a 12th-century abbey converted into a luxury hotel and restaurant, now more or less deserted in the off-season. We both wanted to stay, but doing so would have sacrificed reservations in Rome. "We should come back sometime, in the summer," the boyfriend mused. As the sun set over Umbria's rolling vineyards, it occurred to me that perhaps we should.

Sunday: When In Rome

That was before I realized he'd left our plane tickets, our itinerary, and my carefully researched "places to go" folder in the dresser drawer in Florence.

We circled around and around the center of Rome trying to find either an Internet café or our hotel.

"It's around here somewhere, let's just keep looking," he said, as I silently seethed.