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Our Favorite Tuscan Hilltop Towns

Tuscany has no shortage of tiny, stunning, cobblestoned towns perched high on a hill. Visiting these places in modern-day Italy is like stepping back in time. Many of the original walls, gates and watch towers, harkening back to the Middle Ages or Renaissance, remain despite the test of time. In fact, seismologists have studied this phenomenon, since Italy is no stranger to earthquakes. Apart from the architecture, the other striking feature of these towns is the view. Tuscany is hilly and, without exception, the founders of these towns clearly sought out the most precarious of steep hills and stuck their flags at the very top. The reason for this was to make the towns easier to defend from invaders. The splendid side effect is the unbelievable, breathtaking view of the valleys below.

There are many, many of these towns to explore. One can simply drive through the Tuscan hills for days and stumble upon stunning town after town. Here we explore our top five favorites. A warning— You may be surprised, as crowd-pleasers Siena and San Gimignano did not quite make the cut. Both towns are incredible and not to be missed, but we find the true charm of old world Tuscany tucked away among the lesser-known hills.

1. Montepulciano

Perched on a limestone hill about 2,000 feet above sea level sits Montepulciano, a tiny town that packs a punch in beauty and culture. I’ve heard it referred to as “the jewel of the 1500s” for its impressive collection of Renaissance art and architecture. And it’s known worldwide among wine connoisseurs for its Nobile di Montepulciano, a decadent red varietal. The last time I visited the town, our group wandered off the main street into a wine cellar that unexpectedly led to an enormous underground set of caves where Nobile wines are produced and stored. We loved just wandering the streets, which were unencumbered by tourists. Montepulciano is truly an undiscovered gem of Tuscany.

The focal point in town is the Piazza Grande, ironically named since nothing in this town seems very large. But the Gothic facade of the Palazzo Comunale (Town Hall), complete with bell tower, was haunting enough to capture the imagination of movie makers— It provided the perfect set for a dramatic scene in one of the Twilight movies. This piazza, located at the highest point in town, also houses the town’s cathedral and a grand tower, the top of which provides views of unmatched beauty. What you see below is the Val d’Orcia, a breathtaking valley in southern Tuscany that’s home to most of our favorite Tuscan hill towns.

Following the advice of a friend, our day trip in Montepulciano several years ago included lunch at Le Logge del Vignola, a beautiful and charming restaurant in the middle of town where the owner greets each guest like family. If you go, I’d advise you to first climb many hills around town and work up an appetite. You will want to try everything on their traditional Tuscan menu. If in season, try the porcini mushroom risotto. Montepulciano is also known for pici pasta (pronounced “pitchi”), a hand-rolled sort-of spaghetti that perfectly soaks up any sauce. Wash it all down with a local Nobile di Montepulciano wine. Simply perfect.

2. Montalcino

Speaking of wine, the next town on our list is the capital of the world renown Brunello wines. Although famous for its wines, Montalcino enjoys a tourist-light charm similar to Montepulciano because it is also located in the Val d’Orcia region of southern Tuscany, a fair distance south of Florence. As much as I adore Florence, I also note that the distance from Florence is directly proportional to the old-world charm factor in some of these hill towns. These tourists sure are missing out… shhhhh, don’t tell them!

During our first villa-scouting trip to Tuscany over 5 years ago, we spent 2 glorious nights in Montalcino, since it is the perfect jumping off point for exploring the rolling Val d’Orcia hills and some of Tuscany’s best wineries. We fell madly in love with Brunello, which remains our favorite Tuscan varietal. We also fell pretty hard for the hilly streets of Montalcino. We would rise early each morning, bundle up (this was an early spring trip), and walk the streets, watching the locals drop their kids off at school and pick up the day’s groceries. On market day, we perused the outdoor stalls filled with local fare. Around every corner, there seemed to be another breathtaking view of the valleys below.

A highlight in town is the giant fortress that sits ominously upon the highest hill. You can climb up and walk the ramparts. Of course, on your way back down, you’ll stumble into a tasting room for local wines… you know, in case you’re thirsty from all the climbing. Our two favorite local wineries, which we discovered on a different trip during fall harvest season, are Poggio Antico and Conti Costanti.

If you do visit Montalcino, and I suggest that you do, most any restaurant in town will offer delicious local food. However, our favorite is a short drive from the center of down— Boccon di’Vino is a lovely restaurant with outstanding food, an impressive wine list and amazing views of the valley below. We’ve eaten there each time we’ve been in the area, and would go again and again.

3. Monteriggioni

The sole Chianti town to earn a spot on our list is Monteriggioni, though we can’t emphasize enough the value of exploring the Chianti region for other gems like this. They are there. But we love this one in particular. Monteriggioni’s location on a hill halfway between Florence and Siena dictated its distinct architecture and its fascinating role in history.

It is a tiny town with only one main road, and yet it is surrounded by a giant 13th century wall with huge, protruding turrets. From the outside it looks like the castle that it was built to be, the stuff of fairy tales. Unfortunately for the town, it was the Sienese front of many wars between Siena and Florence over the decades. Eventually an important peace deal was brokered here and it was handed over to the Medici of Florence.

Long before those days, it caught the eye and imagination of Italy’s most famous poet. In The Divine Comedy, Dante uses the image of Monteriggioni as a metaphor for Inferno’s terrifying abyss.

“As with circling round; Of turrets, Monteriggioni crowns his walls; E’en thus the shore, encompassing the abyss; Was turreted with giants, half their length; Uprearing, horrible, whom Jove from heaven; Yet threatens, when his muttering thunder rolls.”

Nowadays it is simply a quaint and beautiful Tuscan hilltop town. We’ve gotten to know Monteriggioni over the years due to its proximity to one of the properties in our portfolio. Casa Storica is a stunning estate that dates back to the origins of the town and is walking distance away, across a picturesque olive grove. We’ve sent happy travelers there over the years, who have enjoyed the beauty of the vast estate and hospitality of the owner family, as much as the proximity to one of Tuscany’s best little towns.

4. Pienza

Not far from Montepulciano, also in the Val d’Orcia region, sits the place that you picture when you close your eyes and imagine the most perfect Tuscan hill town. Set in its breathtaking location high on a hill, dangling over the most stunning views of the valleys below, one may guess why Pienza is known as the ideal city of the Renaissance. But its privileged location is not the true reason.

Pienza was home to Renaissance humanist Enea Silvio Piccolomini, who later became Pope Pius II. He had the money and influence to transform his birthplace village into what he thought of as Utopia, blending Classical and Renaissance aesthetics. He hired famous architects of the time including Alberti for the job, and Pienza became the realization of a dream. A cathedral, papal palace and town hall surround a beautiful central piazza, and a small handful of cobblestone streets meander away until they meet their abrupt ends at vista-point cliffs.

My favorite thing to do in Pienza is wander along the street while Pecorino cheese-tasting. Yes, this is a thing. One of Italy’s most delectable cheeses has its origins in the sheep farms surrounding this town. Pecorino di Pienza is taken very seriously in these parts and is worlds better than its cousin Pecorino Romano, which locals consider to be a salty cheese only suitable for cooking. On a recent visit to Pienza with my mom, she and I walked along the impossibly beautiful main street, ducking into cheese shops and sampling their fare, which was slathered with various toppings such as fig-infused balsamic vinegar. Amazing.

Our favorite Pienza eatery is La Bandita Townhouse Caffe, an outstanding restaurant within a cozy, chic B&B. One would not expect such a modern, high-end foodie gem right in the middle of this tiny, remote Renaissance village in Italy. The owner is a former music industry executive from New York, and he brings a hip vibe to this corner of the world. And by the way he also has an amazing B&B in the countryside right outside of Pienza, called La Bandita Countryhouse, which is in our portfolio of properties. Both the townhouse and the countryhouse are beautifully done, and strike exactly the right chord of relaxation and luxury.

Cortona, one of our favorite hilltop towns

5. Cortona

Topping our list of favorites is Cortona. This is the same town, located about an hour and a half southeast of Florence close to the Umbrian border, that successfully wooed Frances Mayes, author of “Under the Tuscan Sun,” imploring her to drop everything and purchase and renovate a villa. Having visited a couple of times myself, I see how this happened.

As we learn from Mayes’ account, Cortona is a hilltop town with a rich history dating back to the ancient Etruscans. However, legend places Cortona on the map back in biblical times, when one of Noah’s descendants founded the city high on its perch after the Great Flood. Whatever the case, Cortona does have a very special feel to it, with medieval roads and architecture, two small but lively piazzas and spectacular and dizzying views of the valley below.

When my daughters and I visited Cortona for a weekend a few years ago, they were only 8 and 10 years old, but we were all equally captivated by Cortona’s charms. The restaurants were great, the shops were fun, the people-watching was phenomenal. We enjoyed just sitting in the central piazza on a Saturday afternoon as two wedding parties emerged from nearby churches.

After some serious stalking, TTG was able to add to our portfolio of properties Casa del Sole, which is the house at which the movie version of “Under the Tuscan Sun” was filmed. It’s been beautifully renovated since Diane Lane and the rest of the cast occupied the space.

But its charm has not diminished, as you can see. Nor has the appeal of our favorite Tuscan hilltop town. Just looking at the photos of the house and re-reading that old blog post make me yearn to go back to Cortona… or to any of our favorite hilltop towns… or perhaps to find a new one.

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