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In a country with as much rich and easily accessible history as Italy, it can be hard to know where to start. Early this summer, my girlfriend and I planned a week-long Italian jaunt, beginning in Rome and winding our way up to Verona, with a stop in the medieval city of Siena to see the Palio—a famed, centuries-old biannual horse race. In search of a window into a different (less crowded) side of Italy’s history, I took to perusing Airbnb listings in Pitigliano, a southern Tuscan town a Pisan friend had recommended. I stumbled across the Attico Panoramico Nell'antico Borgo—a panoramic penthouse in the ancient city. Lying halfway between Rome and Florence, this apartment was supposedly in one of the most beautiful spots in the region. Looking at photos had me giddy with excitement, but nothing could have prepared me for the sight that opened up before me as our tiny rented Fiat whipped around the hairpin turns of the Tuscan hills and Pitigliano came into view.
While the archaeological record shows evidence of a pre-Roman Etruscan town on the same site, the current incarnation of Pitigliano has existed since around the 11th century, when it quickly rose to prominence as a regional cultural and political capital. Known as the “Citta del Tufo” in reference to the ubiquitous volcanic tuff stone used in its construction, Pitigliano is perhaps the quintessential Tuscan hilltop town: a labyrinth of clifftop walls, towers, houses, and churches that could easily have been ripped from the background of a Bellini painting. After parking outside the city walls—no cars allowed in the centro storico—we traversed the ancient stone bridge that led to the old city, which is perched on top of a rocky outcropping (a strategic decision dating back to the days when the town regularly found itself at war with its neighbors). Despite (or perhaps because of) its imposing defensive exterior, the inside of the town is peaceful; its tiny size concealing a seemingly endless maze of winding alleys and idyllic squares, strewn with marble fountains, pots of flowers, and stray cats.
After picking our way through the stone streets to the central Piazza della Repubblica, we spotted the ancient stone building we were to call home. Inside, under the huge beams of the gabled ceiling, the apartment seemed as labyrinthine and storied as the town itself, with each of its cozy rooms containing a treasure trove of tasteful, eclectic decor, from original oil paintings to Etruscan-style pottery. Small, quirky, and full of life, it’s the kind of space that could easily feel cramped or cluttered if it weren’t so thoughtfully designed at every turn. A wealth of south-facing windows filled the home with warm Tuscan sunlight, from the delightfully spacious king bedroom (there’s also a charming daybed in the adjoining room that sleeps a third traveler) to the compact but attractive kitchen. As pleasant as the interiors were, we spent most of our time at the highlight of the penthouse: its two (two!) clay-tiled terraces. Stepping outside, I understood why they called it the “panoramic penthouse”, with views across the entire town and down into the forested ravine below.
Pitigliano, while small, provided the perfect home base to explore the surrounding region, one of the most beautiful in Italy. The town itself had a wealth of shops, streets, and churches to explore, and was even home to a medieval synagogue (the town was once known as the “little Jerusalem of Italy” thanks to its thriving Jewish presence)—all within steps of our Airbnb. With delightful trattorias around every corner, we were always excited to return in the evenings to fill up on pasta and wine, before wandering home to our gorgeous apartment for a restful night’s sleep. During the day, the weather was hot enough to require a swim. Thankfully, the coast was less than an hour away by car. I recommend heading to Monte Argentario, a peninsula so beautiful, so perfect, and so much of a hidden gem that I almost forwent mentioning it, preferring to keep the secret to myself. With an Amalfi-esque coastline and beaches rivaling those of Cinque Terre (but with a fraction of the crowds), it’s a slice of heaven, and one that in-the-know Italian visitors rightfully prefer to keep under wraps. Renting a scooter proved the best way to traverse the area’s winding cliffside roads and picturesque towns—or so we thought. We enjoyed ourselves so much that we went back the next day and rented a boat, which was somehow even better.
Sitting on the terrace that night at our Airbnb, enjoying the sunset with an aperitivo in hand, I felt a glow of self-satisfaction; “So this is how you do Tuscany.”
