Our waiter, Giado, covered his eyes in dismay when we told him we were setting off the next day on a weeklong walking tour of Tuscany. "You really want to walk? It's sometimes 16 kilometers [about 10 miles] from one town to the next, with nothing in the middle to eat or drink." His concern seemed genuine, and given that we'd just demolished two of Osteria le Logge's most amazing desserts—a mascarpone terrine with port granita and a chocolate panna cotta with lavender cream—somewhat justified. Nearly every window in the city of Siena displayed something I wanted to eat: biscotti, lardo, wheels of pecorino, bresaola, cones of gelato. I knew we wouldn't find much of that while footing it through hay fields.
But my mom, my sister, and I had come here to start a seven-day trek through Italy's villages—we wanted to really experience the countryside, not just drive by it. Everyone has a fantasy of what Tuscany looks like: old stone farmhouses, rolling fields, lines of cypress trees. (Admit it: You've seen Under the Tuscan Sun at least once.) That was certainly our terra cotta-colored vision, and we were convinced that a self-guided tour was the only way to live the dream. Countless companies offer walking tours in Tuscany; we chose an outfit called Girosole because it was run by locals passionate about their homeland and intimately familiar with the best walking routes. The company allowed us to start our trip on any day and add extra nights in a given location, in the event that we couldn't tear ourselves away from a favorite sliver of la bella vita. For $1,390 per person for eight days (in high season), the company booked our hotels, provided walking directions (and a cell phone in case we got lost), and supplied a driver who transported our luggage—and sometimes us—from hotel to hotel. The self-guided option left us free to start our days whenever we pleased and walk at our own pace without contending with anyone else's schedule or group dynamics. Neither my mom nor I are regular hikers, but my sister is a marathon runner, so having the services of a driver gave Mom and me an out: If we were too lazy-or worn out-to walk one day, we could always hitch a ride with the bags.
Our driver turned out to be not one person, but two: Paolo Forti and his son, Giacomo. Giacomo, 27, wore oversize Ray-Bans and was exceedingly (and adorably) polite when he picked us up in Siena. He opened doors, carried our bags, and on the way to Montalcino, where we started our trip, he narrated the scenery, pointing out the small town where he grew up, offering advice on his favorite wines, and telling us to look for rosebushes planted at the end of every vineyard row. "The rose and the grape, they take the same element from the ground, so the farmer, he can know if the land is good for the grape," he said, in charmingly accented English.
When we reached Montalcino, Giacomo handed over a set of maps and customized directions, and then we were off and walking. For us, a typical day started at 9 A.M., and we often set out right from the front door of our hotel-in this case, Hotel dei Capitani. We'd wind our way down from one of the jewel-like hilltop towns we stayed in, looking back to see the fortified castle of Rocca d'Orcia recede behind us on one day, the walled town of Montalcino the next. Then we were crossing fields of hay that waved in the wind, fording rivers next to stone bridges destroyed during World War II, and passing row after row of heavily pruned grapevines, all while following our endearingly quirky walking directions: You arrive at another open meadow. Keep right through the next fork just past the small ruined church. The trail bends into a gap in the brush. They seemed cryptic out of context, but on the trail they made perfect sense. One leisurely walk led to Bagno Vignoni, a spa town where people have taken the waters since Roman times-thermal pools still bubble and boil there. We scrambled across cliffs that spewed hot, sulfurous water into turquoise pools, dined at a restaurant beneath a fragrant acacia tree, then soaked our feet in the warm mineral water that flowed through channels carved into the rock. Heaven.
We'd usually make it to the next town for lunch, but twice we stopped at a grocery store before setting out and bought picnic provisions: prosciutto, pecorino made from local sheeps' milk, Sicilian blood oranges, fresh-baked bread, and a thermos of red Brunello-we were, after all, in wine country. One day we waded through knee-high grass into an olive orchard and sat beneath the trees, our jackets serving as a picnic blanket. I picked a tiny stalk of wild onion sprouting delicate purple flowers and presented it to my mom, who wore it in her buttonhole.
Mom was almost giddy from all the gorgeousness. She couldn't stop hugging us and saying "I'm so lucky!" My sister and I rolled our eyes, but secretly we agreed. Girosole sent us on a path through the Orcia River valley (Val d'Orcia). It's an area of such well-preserved agrarian beauty-where cypress trees and crop rows trace the same lines they did when this land was first farmed-that it's been declared a UNESCO World Heritage Site. It's the place where the concept of man-made landscape began, when the wealthy merchants of Siena laid out plots of land in the 14th and 15th centuries with the aim of making them not just manageable, but also aesthetically pleasing. We felt like we were walking through a 600-year-old period set piece, where every field, tree, and house was placed just so, and around every corner was another equally cinematic view. Let's just say we took a lot of photos.
Throughout the trip, we were in daily contact with Giacomo or his father, and when they came to collect our bags, we'd pepper them with questions. One morning, we asked Giacomo about a massive building we'd seen in the distance, which he explained was a hotel dating back to the Middle Ages built to house religious pilgrims. During Caesar's time, the main north-south byway cut through the Val d'Orcia. Later, in the 7th century, Christians traveled by foot on their way to Rome, and it remained a pilgrimage route for a thousand years. Monasteries and inns sprang up to serve the travelers, but by the 17th century, the road fell out of fashion. But those earlier journeyers left behind a province perfect for strolling, where scenic lowlands were punctuated with hilltop fortified settlements, most of which were located less than 10 miles-a manageable day's walk-from another town.
Remnants of this once-illustrious route are sprinkled throughout the Val d'Orcia. Just after passing through the hamlet of Villa a Tolli (which was so deserted I had to use my camera's self timer to photograph the three of us in front of a dreamy stone house covered in climbing roses), we rounded a corner and saw the Abbey of Sant'Antimo, its bell tower peering above the countryside. The abbey was built and rebuilt many times, first in the 700s by Lombard kings to house pilgrims. Its current form is gracefully curved in a rare French-Romanesque style, dotted with prehistoric-looking carvings of monsters and oxen and men. Close up, its massive building blocks seemed to glow from within.
There were other visitors at Sant'Antimo, but we spent most days in splendid isolation, encountering almost no one-just us and fields of poppies, thorny brambles of wild roses, stone walls blooming with irises, and clumps of rosemary as big as bushes. We walked right up to the iconic Cappella di Vitaleta. Flanked by two rows of towering 40-foot cypress trees, this tiny chapel is reportedly the most photographed church in Tuscany, but it's reachable only on foot. We had it all to ourselves for almost an hour; to celebrate our private tour, my sister and I turned cartwheels right on the lawn. Similarly deserted was the Collegiata church, in the slumbering town of San Quirico d'Orcia. Its entrance is flanked by delicately knotted columns resting on the backs of fantastical lions while scaly monsters tangle in battle above the door. Though it was designed to make 13th century pilgrims cower before the power of the church, we modern-day travelers were just as awed, dwarfed and alone before those spectacular stone beasts. When we saw Giacomo again, we asked him where everyone was. "The Italians, they don't walk," he said. "They come by car, they have lunch, they have a coffee, then they get back in the car."
The under-populated countryside stood out in blissful contrast to the teeming villages where we spent our nights. One day, as we lingered outside a ceramics shop, surveying the valley we'd just walked through, we overheard another tourist. "Okay, this is our third town today. Are we done yet?" While they rushed on to Florence or back to Rome, we spent leisurely afternoons and evenings poking around in boutiques, gaping at medieval architecture, and strolling the narrow lanes. In Pienza, we saw a group of little old ladies gathered at the end of a cobbled street, knitting. In Montepulciano we sat outside drinking glasses of the famous Vino Nobile in a piazza and slept in a hotel, L'Agnolo, that felt more like a cathedral, with glorious frescoes painted on the ceiling of our room. And we happened to be in Montalcino on the day the town celebrates its patron saint, Maria SS del Soccorso, so we were treated to July 4th-worthy fireworks bursting over a fortress; afterward, a DJ blasted tunes in the square, and we found ourselves dancing in the streets to "Another One Bites the Dust."
In truth, our appreciation for these towns was heightened because of the effort it took to get to them. Which is another way of saying that touring Tuscany by foot wasn't always a walk in il parco. Take, for example, our march to Montepulciano; the hike took longer than expected, and after five hours without food, we could hear one another's stomachs growling. We were so hot and tired that when we skirted an olive orchard and the Temple of San Biagio suddenly rose above us, we thought we were seeing a mirage, conjured up to give strength to hungry passersby. Glowing golden in the sunlight, drawing us in, its dome looked like something out of a Renaissance masterpiece.
And yet, despite our grumbling bellies, it was impossible not to stop. Inside, the church's cool air and silent beauty seemed to cure our weariness. A diffuse light fell from the dome in a perfect circle, and we were surrounded by arches and rosettes and Greek columns, all carved out of the same linen-colored stone. As our eyes adjusted to the darkness, I saw an automated tour guide called an ArtPhone. I dropped a 1 Euro coin into the slot and learned that in 1518, a fresco of the Virgin painted on this spot suddenly seemed to smile. Many people witnessed the miracle, and public funds were collected to build a commemorative temple. San Biagio, one of the world's finest examples of Renaissance architecture, has been providing refuge for religious pilgrims-and weary hikers-ever since.
When we headed back outside, our empty stomachs were filled thanks to another miracle. Directly across from the church, far from the city center, where we least expected to find a restaurant, I spotted La Grotta, reportedly home to the best food in Montepulciano. We weren't exactly dressed for a fancy lunch. Yet when the maitre'd, impeccable in his tailored navy suit, heard that we'd walked all the way from Monticchiello-five miles, uphill all the way-his eyes widened and he ushered us (shorts, hiking boots, and all) to a prime table in the back garden. He brought an extra chair for our hiking gear, recommended a bottle of the house red, and let us order dessert long after the restaurant had closed. We were several paces down the road when he came running after us with a half-empty bottle of water we'd left behind. "You will need it for your walk!" he said, sending us on our way with a wave and a "Ciao!"
Bustling Montepulciano was full of trattorias and wine shops, but our favorite town was the emptiest: Rocca d'Orcia. There we found a crumbling castle looming over stone streets barely wide enough for cars (not that we cared about that!). When we arrived, an elderly man, navigating rocky steps worn smooth by the footfalls of several centuries, greeted us with a "Buon giorno." Otherwise, all was silent. We were staying at Cisterna nel Borgo, a three-room hotel above the town's only restaurant, where owner Marta Catani also gives cooking lessons, though she herself has no formal training. "Italians don't go to cooking school," she explained. "You just watch your grandmother." At dinner, we stuffed ourselves with tender, tangy wild boar cooked in yogurt and sauteed pork in a honey sauce that was salty and just a bit sweet. Since we were the only guests, we each got our own room; mine had a wood-beamed ceiling and windows overlooking the town square, which was dominated by a massive well. Marta told us that until the late 1950s, the city gates were locked against intruders every night, and today just 26 souls live within the town's walls. For two glorious nights, we were happy to push the population to 29.
On our last morning, we were feeling lazy and not up to the challenge of a nine-mile walk. When Giacomo's father, Paolo, came to collect our luggage in the morning, we asked if he would drop us off at the halfway point. "Si, si," he said. That morning, instead of huffing up hills, we strolled through Monticchiello, a beautifully preserved walled town. We craned our necks to get a look at the top of the thick defensive tower at the town's entrance, then passed beneath a stone archway and into the winding medieval streets, flanked by the high walls of houses made of uniformly honey-colored stone. We walked down lanes no wider than a horse, took photos of laundry hanging from shuttered windows, admired a vintage red Fiat parked by a church with a vaulted interior covered in flaking frescoes, and read the plaque on an obelisk-shaped World War I memorial. On the way out of town, we encountered a crew of maintenance men. They waved. We waved back. "Ciao bella!" they exclaimed. Yes, we thought. It was beautiful.