I was 19 when I woke up one morning in a Tuscan casa colonica—a classic 18th-century stone farmhouse designed to shelter a large family on the second floor and its beasts in the arched stalls below. It stood on a terrace beneath the medieval hill town of Cortona. The house, charmingly converted in the Anglo-Italian style, belonged to the mother of my college roommate, Beatrice, who had invited me to spend the summer of our senior year. We had driven up from Rome the night before. I awoke to the aroma of espresso and the throaty voice of Lola, the part-time maid, singing as she hung out the laundry. A bee hummed in the wisteria that clung in dewy garlands to the window frame. I threw off my homespun linen sheets and unlatched the shutters to a view of silvery blue hills, a golden valley, a Renaissance tower set in an allée of cypress trees. Everything was thrillingly exotic to me, yet I felt that I was finally where I ought to be: the girl from Queens had come home.
Last summer, I returned to tuscany with my 10-year-old son, will, my husband, Peter, and my extended American family—a crew of adopted "siblings" and "cousins." Through the Internet, we had rented a four-bedroom casa colonica—with a chef's kitchen and a library full of books and games—that was furnished much as the Cortona house had been, with elegant but sturdy antiques that gave off a scent of beeswax. We had considered a vast array of accommodations in every part of Tuscany, but we chose a lush and tranquil southeastern corner near the thermal spa of San Casciano dei Bagni—a health resort since Roman times. Our house had a luxuriant lawn, a rose garden, a grape arbor, and a swimming pool—an essential luxury in the heat of a Tuscan August. It also had a television set, but we never turned it on.
Here I have a confession to make. We didn't think too much about the kids—three boys, ages 11, 10, and 9, and a towheaded bambina of 4. It's not that we ignored them: we were just rendered incapable—by beatitude—of being anxious about anything, including their entertainment. The adults cooked companionably, napped in the hammock, and read the dog-eared books in the library. The kids responded to the shocking relaxation of parental prepotenza by becoming enterprising on their own behalf. They dug out an ancient chess set, fished frogs out of the pool, picked tomatoes from the vine and pears from the tree, and adopted a chameleon. After a week, they had learned enough Italian to order gelati and to say "mille grazie." And they repaid our confidence by improvising their own version of an old-fashioned Tuscan holiday, steeped in sensuous well-being and dole far niente.
This is not to say that we never budged from home. As I was the old Tuscany hand, I became the cicerone—the family Vigil. And that was a daunting charge. The region is so rich in scenic beauty, culture, and history that a lifetime of exploration—much less a 10-day vacation—can't begin to exhaust it. The question is not so much how to order up a Tuscan banquet as how to digest it.
Here is my recipe: Choose the freshest local ingredients, then don't complicate them too much. No heady stews of culture, no pyrotechnics in the rental car; in fact, not much ambition at all. Spice indolent days in your country redoubt very lightly with some sightseeing—but save Florence for the off-season—or better still, send the kids back on their own a decade from now, with a backpack and a first love, to discover its painted ceilings.
I plotted our excursions around the haunts of my youth. One of our day trips began in Arezzo, home of Piero delle Francesca. We arrived early and got tickets to see Piero's luminous frescoes in the church of San Francesco later that day. The frescoes have been under restoration for several decades, but the scaffolding in the chapel made it all the more alluring for the kids—"a museum," said my Will, "with monkey bars."
My friends know that my motives are never entirely high-minded: Arezzo has perhaps the greatest concentration of antiques shops in Italy, and on the first weekend of every month, there is a mammoth fair in the Piazza Grande. Hundreds of dealers bring their wares—everything from palazzo furniture and Renaissance Madonnas to inexpensive prints and pottery. We moms, intoxicated, staggered from stall to stall, bargaining for embroidered linens, mosaic jewelry, and picture frames. The dads found a vintage Bugatti to pine for. And the kids, who had been scoping out the armor, antique toys, and circus posters, hopefully suggested that we could save money on shipping by stuffing the car's trunk with our acquisitions.
Later that afternoon, senza Bugatti, we headed south to Cortona, home of my second great love among Tuscan artists, Luca Signorelli. (His frescoes of the naked and the dead being carried off to hell by devils inspired Freud to write The Psychopathology of Everyday Life.) "Signorelli is the kind of guy," I told the boys, "whose work can give you some really neat ideas for next year's Halloween costume." As we navigated the hairpin turns that lead up to Cortona from the Val di Chiana, I pointed out Francesco di Giorgio's magnificent church of Santa Maria del Calcinaio—one of the first jewels of the Renaissance. The kids were more impressed to learn that as teenagers, Beatrice and I had totaled our motorbikes on this same route. We arrived in one piece, just in time for sunset Camparis and spremuta of blood oranges on the panoramic terrace of Ristorante Tonino, in the Piazza Garibaldi. The shops were reopening, and my friend Michael was tempted by a white Borsalino, its straw the texture of raw silk. His wife, Harriet, and I were tempted by an opera, about to be performed on a fantastically painted portable theater in the main square. The music was Verdi, but the faces, the illumination—the whole dreamy spectacle—was Fellini.
After a restorative day of trollope and frog catching, we set out for Montalcino, whose loamy earth yields Italy's greatest wine, Brunello. It is also home to my college friend Beatrice. Her oldest daughter, Camilla, leads backcountry riding trips. The kids were ecstatic at the chance to meet her colt and muck out her stables. We were ecstatic at the chance to troll the farmers' market, stocking up on espresso pots, fresh porcini, cheap-chic velvet bedroom slippers, and, of course, a provision of young Brunello for laying up. We rejoined Camilla and the kids, by now smelling pungently of wild rosemary and manure, at the 14th-century fortress in Montalcino. There they fought imaginary wars in the ramparts.
As a light rain began to fall, we corralled our knights and maiden for a 40-minute drive on two-lane roads through the austere landscape of the Sienese crete (clay ravines). We were heading for the late-medieval abbey of Monte Oliveto Maggiore, just above Buonconvento. Its Great Cloister would reopen at three, and in the interval, we lunched under the umbrellas of the Ristorante La Torre, situated within the abbey walls. We discovered that the abbey gift shop sells a selection of herbal remedies made by the resident monks—including, pertinently, an aromatic digestive tea.