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Top Six Hill Towns in Tuscany

Tuscany is one of the few spots on earth that is just as divine as it is in the movies. The endless vineyards, sunflower fields, and perfect rows of dark-green-almost-black cypress trees splash against blue skies and orange sunsets.

It would be easy to forget that amidst all this nature is a great deal of man-made beauty. The art, architecture, and cuisine in Tuscany are almost overwhelming in their volume and richness. There is so much to absorb, you might wonder where to start.

Here are the top six hill towns to visit in Tuscany.

San Gimignano

San Gimignano is one of Tuscany’s more famous villages, nicknamed the “Manhattan of the Middle Ages” for its fourteen impressively tall towers, the only ones surviving of the original seventy-two. The town dates to at least 929 A.D., and it has not changed much since then except for the souvenir shops everywhere. (If you are planning on buying some typical, colorful Tuscan pottery, or brightly patterned table linens, this is the place for it.)

Make sure to stroll through Piazza Duomo and Piazza della Cisterna, and do not leave without a lunch of mixed meats and cheeses, a glass of white Vernaccia di San Gimignano wine, and a giant cone of gelato. Work off the calories by climbing the winding steps to the top of the Torre Grossa, taking in the bird’s eye view of the town, and 360 degrees of Tuscan countryside.


Just south of San Gimignano (you can see both in the same day), Monteriggioni does not look like a town from the outside. All you can see from the road is a thick stone wall with one arched, gated entrance, making it look more like a castle or even ruins.

But if you park the car and walk through the gate, you will find a perfectly preserved medieval village inside. During the Middle Ages, the Sienese built Monteriggioni as a defensive fortification against the Florentines. But the walls that once kept enemies out now welcome visitors in, and the quaint alleys and squares behind them will make you feel like you have stepped into a time machine.


If you do one wine tasting on your Tuscan holiday, do it in Montalcino, known worldwide for its namesake Brunello. Over thirty years ago, Brunello di Montalcino was awarded Italy’s very first Denominazione di Origine Controllata e Garantita (DOCG) distinction. Both in the town itself and in countless farms and wineries in the area, you can taste and buy it by the glass or bottle. But because man (or woman) cannot live on wine alone, you can pick up some superb cheeses, meats, and bread in one of Montalcino’s countless salumerie and –ecco!– you’ve got a Tuscan picnic.

In case you need another reason to visit, Montalcino itself is small and lovely, with sweeping vistas of the countryside, and featuring a 14th-century pentagonal fortress. One more reason? The nearby Abbey of Sant’Antimo is a thousand-year-old Benedictine monastery still in use today by a small group of monks,
whom you might bump into during your visit.


Eating and drinking in Montepulciano is practically its own art form, so you might forget to look up from your plate to enjoy the views and Renaissance architecture as well (including 14th-Century town walls). Archeological discoveries indicate that the town existed three or four centuries before Christ, giving the locals plenty of time to perfect their decadent cheese, honey, liver pâté, and pork productions. This is the place to get gifts for the gourmet chefs back home. And do not forget the wine, as Montepulciano’s Vino Nobile is widely recognized as one of Italy’s most delicious, and oldest, varietals. You can stop into just about any shop and sample the goods before purchasing a few bottles to take with you.


Between Montalcino and Montepulciano sits Pienza, a UNESCO World Heritage Site, used as the set for the films “Romeo and Juliet” and “The English Patient” for its beauty and remarkable preservation. Important for both art historians and architects, Pienza is considered a perfect representation of quintessential Renaissance architecture and egomania: Pope Pius II’s scheme to turn his birthplace into a utopian city was begun but never finished. What is left is an oversized town square with a photogenic wishing well, cathedral and city hall.

Behind the square, Pienza’s altitude gives it a natural balcony from which to marvel at the serene Val d’Orcia below.


Maybe “Under the Tuscan Sun” is what made Cortona world-famous in the last couple of decades, but Cortona was always world-class. Nestled in the Val di Chiana close to the Tuscany-Umbria border, Cortona’s position slapped against the side of a hill means narrow, steep streets and wide, valley views. Renaissance art and architecture lovers will get chills over the 16th-Century Santa Maria Nuova church, and 15th-Century panels by Fra Angelico in the Diocesan Museum.

Just outside of town sits Eremo le Celle, the beautiful, peaceful monastery where St. Francis of Assisi secluded himself for two years. His cell remains unchanged, but you may not.

This post originally appeared in the summer 2014 magazine. It is by Nashville native Liz who is on her second stint in Italy. An attorney in the States, Liz does many things in Rome and says that “Life here is about 80% more difficult but 90% more fun.” She blogs about her Italy at http://romeifyouwantto.com/.

Published July 25th, 2016 by ErinAbroad
Posted to Travel Blog

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