The Creator made Italy from designs by Michaelangelo. – Mark Twain

Tuscany’s Best Hill Towns

My fascination with Tuscany continues. During our four-day road trip through the region’s iconic rolling hills, my mom and I uncovered ancient labyrinths, tasty wine and epic panoramas. Luckily, we had access to Tuscany’s best hill towns with our own car – which made exploring much, much easier! We enjoyed Gothic Siena first, and used our base in Pienza to explore neighboring Montepulciano and Buonconvento. Then, the sister cities of Volterra, Pisa and Lucca ended our hill town discovery.


Gorgeous vistas of Tuscany

So which Tuscan oasis wins the prize for best hill town? Well, each is just so diverse and unique in its own special way, but let’s take a look at a few of them.

Montepulciano – Are you a wine-lover? Then definitely visit Montepulciano. The Vino Nobile di Montepulciano, a robust red, is one of Italy’s best vinos. Wine-tasting showrooms and deep cellars pepper the city’s lanes, offering tours and tastings. You can spend hours roaming this tiny town’s cobbled streets, lingering in bodegas, tasting the creamy saltiness of pecorino cheese, and chatting with friendly locals.


Can the view get much better?

A stop in Montepulciano isn’t complete without a visit with Cesare, a renowned coppersmith whose family has been crafting hand-hammered copper pieces for decades. His storefront, the Mazzetti copper shop, sits along Via Volt Nel Corso, and the shop flaunts some of Italy’s highly-prized copper vessels. Cesare’s workshop is on a hill behind the store, and is chockablock with antique tools and photos of his friends from around the world. Cesare is genuine, gentle and gregarious, and his eyes simply twinkle when talking about his craft.


Coppersmith Cesare

Volterra – Perhaps best recognized as the ancient Italian city where the Volturi reside in the Twilight series, the hill town of Volterra indeed has a true medieval vibe. The village has remarkably well-preserved fortressed walls, a gate from the 3rd century B.C and remains of an ancient Roman amphitheater and bathhouse. Butter-hued walls ripe with green shutters trail from the ancient structures, giving the town a truly captivating ambience. Even Volterra’s crumbling, graffiti-covered lanes are enticing and photo worthy!


After discovering Volterra’s various nooks and crannies, we followed a worn cobblestone path to the central square and found lunch at a nearby cafe. Our grilled paninis with provolone cheese and succulent, peppery olive oil were a highlight of the day.


Pienza – Our home base in Tuscany was nestled just outside of Pienza in the lovely Val d’Orcia. Here, cypress trees hug winding country roads, and fields of poppies, lavender and golden hay stretch to the horizon. Hills drift seamlessly into shades of juniper, chartreuse, jade and sea foam, and the sunsets are a soul-stirring gift from nature.


Tuscany’s epic views were mesmerizing!

Pienza’s sand-colored stone palazzi and city center, a UNESCO World Heritage site, are most delightful in the early evening. Locals linger in passageways, and delectable aromas ride on sweet breezes. Our most memorable Pienza experience took place at a nondescript pizza shop. We were greeted with a welcoming smile and wrapped in the comforting scents of yeast and fresh basil. Watching the pizza chef’s performance was a mesmerizing dance, and better yet, our pizza was the perfect mix of salty crust, oozing cheese and garden fresh vegetables.


Pizza – – yes, please!

Pisa – Yes, Pisa is home to the renowned Leaning Tower, and yes, that is the main reason why we visited. Pisa lacks the medieval grandeur displayed by other hill top towns; however,  there are myriad churches, palaces and city squares from the 11th to 13th centuries to fawn over.


The typical Leaning Tower photo, of course.

The Leaning Tower, or Torre Pendente, is one of Italy’s signature sights. The iconic tower leans an astonishing 3.9 degrees off the vertical. We took the mandatory photo amid all of the other tourists, and then moved on. A centrally located food market near the Piazza delle Vettovaglie provided a great stop for mid-morning coffee and treats.


Cappuccino, cafe and sweet treats.

Lucca – Located just an hour west from Florence, Lucca is not technically a hilltop village. The main attraction is its pedestrian promenade. Set atop its fortressed walls, the path is lined with lush grasses and trees, perfect for biking and strolling on a hot afternoon.
Other interesting sights include Lucca’s Duomo, which flaunts icing-like architecture, and the Piazza Anfiteatro, reminiscent of an ancient Roman amphitheater. The square is crowded with souvenir stalls, markets and crinkly men playing bocce. Relaxing with a glass of wine to simply people watch is an enjoyable experience.

Siena – Though the outer circles of Siena are extremely difficult to navigate with a car, its city center is closed to traffic and resplendent with colorful facades and brilliant architecture.


Visiting the heart of Siena, the PIazza del Campo II, is certainly an experience to remember. It’s nice to just sit in the Piazza with a gelato to fully absorb the atmosphere. The Piazza has a unique shell shape and a red brick-lined pavement. All for the surrounding buildings, including the city hall and 330-foot tower, face the square. It is certainly one of the best city squares in all of Italy. Sampling the Sienese specialty of panforte and witnessing its majestic Duomo are other highlights for curious travelers. We ambled and wandered for an afternoon, getting lost in Siena’s lanes and ducking into many bakeries and shops.

So, with all of these wonderful hill towns, I simply cannot choose a favorite. I love them all for different reasons. How about you? Do you have Tuscan hill town that you wish to return to?