The romance of a Tuscan road trip

Halfway through our Tuscan road trip, between two famously beautiful drives—the Val d’Orcia and the Via Chiantigiana—we find ourselves lost. Part of the route we had plotted is temporarily closed, so we follow our noses, and soon we’re bumping down a strada bianca, a white road, so-called because they’re unpaved, the dusty gravel crunching under our tires and leaving a cloud in our wake.

But this is far from a disaster. This region of Italy is famed for many things: Its ancient cities of Florence, Siena and Pisa, rich with Renaissance art and iconic architecture. Its world-class wine. Its prized truffles and pasta. Its distinguished designers. And then, of course, there are its astonishingly beautiful landscapes where, around each snaking turn, you’ll find yet another breathtaking view of a verdant valley or historic hilltop town.

Our journey begins and ends in Florence, a city that is becoming increasingly pedestrianized—and harder to drive into, with one of Italy’s many urban zone a traffico limitata (limited traffic zones), where fines are easy to accumulate. So, rather than picking up our rental car from Florence Airport straightaway, we hop on one of the cheap, speedy trams into town, and spend our first 24 hours cramming culture (the Uffizi Gallery’s Botticelli paintings), vintage shopping (San Spirito’s superb market) and sunset aperitivi (snacks and spritzes at Hotel Continentale’s chic rooftop bar, La Terrazza, with its views across the River Arno).

The next morning, we return to Florence airport to pick up our rental car, and are soon on the road. We’ve plotted a clockwise loop, a jagged oval skewing south southeast. Our first destination is Montepulciano, a hilltop town famous for its wine, on the western edge of the Val d’Orcia, a valley so beautiful it’s been made a UNESCO World Heritage Site. Barely are we on the highway, however, before my copilot declares we need to make an emergency stop: a very worthwhile seven-minute detour to The Mall Firenze, a temple to every major Italian designer, with deep discounts and a clientele so chic, we even spot a baby in a trench coat.

Refueled by high fashion and strong coffee, we rejoin the A1, and after an hour on the highway, peel off onto a country road and begin to climb the 1,985 ft hill on which Montepulciano perches. Its maze of honey-colored stone streets provided the setting for one of the Twilight films, while San Biagio church was featured in Under the Tuscan Sun, but wine is the star here. Every door seems to lead to a wine cellar, and its Nobile di Montepulciano is one of Italy’s oldest varieties, first documented in 789 CE. “Red wine in Tuscany is like an institution—50 years ago, nobody drank white wine here,” says Francesco Maramai, a sommelier who has served Hollywood stars and a former U.S. president at his family’s restaurant and wine cellar, Osteria del Borgo. (Read more about wine tasting in our perfect pit stops, below.)

Our drive the next day takes us into the Val d’Orcia, through velvety, luminous green valleys studded with poppies. To say it is breathtaking is to undersell it; each new vista of rolling hills and perfect avenue of cypress trees striking you dumb. The 15th-century Pope Pius II built his summer residence here, in the tiny town of Pienza, which was conceived as the ideal city; and after pausing in his serene garden, it is hard to disagree.

We pause for lunch in the wisteria-draped main square of Bagno Vignoni, which takes its name from one of the natural hot springs found across the region. Renaissance architects channeled the waters into a perfectly rectangular pool, but as our waitress tells us, you can’t swim in it; instead, she recommends heading further south to local favorite, Bagni di San Filippo (see below).

Tonight, we are staying in the tiny medieval village, Lucignano d’Asso, where the local bar has a docile visiting fox and excellent food, while our accommodation, Borgo Lucignanello Bandini, has a hilltop pool, and apartments with pretty bathrooms in grapevine tile and towels monogrammed with a cursive P. This, it transpires, is for its Sienese owner, Angelica Piccolomini, whose ancestors acquired the village in 1485, and whose family tree includes a certain Pius II. The hotel also arrange our next morning’s activity: a trip with a truffle hunter (see below).

The last leg of our journey takes in another storied stop: the medieval city of Siena, with its seashell-shaped Piazza del Campo. In July and August, the grand piazza hosts the annual Palios, raucous bareback horse races pitting the city’s ancient wards against each other. Today it is merely mobbed by tourists; after finding a spot in one of the bigger car parks outside the city walls, we happily join the throngs to soak up the history.

Back on the road, we join the SP222, also known as the Via Chiantigiana—named for the Chianti wine region through which it winds. As Maramai warned us at our wine tasting, you could drive from Siena to Florence in just over an hour; but the undulating, snaking switchbacks of SP222 are not about speed. This is a route lined with densely forested hills, ancient olive groves, and the neat stripes of vineyards—hence its other name, the “Strada del Vino.” It’s a route to be lingered over like a lazy lunch, where the landscape is as much to be celebrated as a glass of Chianti Classico. With a plate of tagliolini al tartufo, of course.