Intimate Italy Like You've Never Seen It!
How one Budget Travel writer turned a dream—experiencing Italy like an Italian—into a reality with an affordable, completely doable walking tour of Tuscany.
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.