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Southern Tuscany

Things to do in Southern Tuscany

Many travelers planning to go to Tuscany end up staying in Florence or in the nearby Chianti region. But venture just a little further south, where the rolling hills of olives and grapes become more dramatic and where the Medieval hilltop towns are a little less discovered, and you are in the paradise of Southern Tuscany.

There are many incredible towns to explore. Here are a few of our favorites…

Pienza & Montepulciano

These famous Tuscan towns are a mere 20-minute drive from one another. They are both extremely charming with their medieval cobblestone streets and open piazzas. Walking the towns leads you from one lovely shop/cafe to the next, and around each bend is a shockingly gorgeous view of the surrounding Val d’Orcia (valley) and hills. Montepulciano is known for its red wines, including the Nobile wines, and reminds one of Siena or San Gimignano on a smaller and less touristy scale. Pienza is a quaint town worth roaming through one afternoon or evening. There are a number of great restaurants and authentic Tuscan ceramic and linen shops.


This tiny gem of a town is the locale of the famous book and movie Under the Tuscan Sun. It’s easy to see why the author fell in love with this town enough to move her life there. Cortona is oriented roughly around two piazzas. The smaller one, Garibaldi, is a tiny round piazza with dizzying views of the countryside below. A couple of blocks away is the slightly larger Piazza della Repubblica, which, with its charming cafes and shops, is fantastic for people watching. If you are brave enough to venture up to the top of the steepest hill, you will be rewarded by the sight of the church of Santa Margherita, who is the patron saint of Cortona. It’s simultaneously lovely and eerie, with her mummified remains displayed at the altar.


Famous for its Brunello wines, Montalcino is a glorious hilltop town perched high above the rolling hills of the Tuscan countryside. The Brunellos are those wines aged for at least 5 years, but the less famous, Rosso di Montalcino wines are only aged one year and offer a delightful taste of the Sangiovese Grosso grapes. There are many sights to see in this medieval village, including the Fortress located at the highest point of the town. The fortress is also a fun place to taste the local wines. Just steps from the Fortress, the Farmers market expands down one of the side streets every Friday morning. You can find anything from fresh pastries and fruit to jewelry and clothing. It’s a fun way to spend some leisurely time strolling the stalls overloaded with local faire. Montalcino is a very walkable town, that can be explored within an hour, maybe longer if you stop to linger, which you definitely should.

Near Montalcino

Abbey of Sant’Antimo in Tuscany

On your way to or from Montalcino, a worthwhile stop is at the Abbey of Sant’Antimo, a former Benedictine monastery rich with history and beautiful architecture that beckons you to pull over and explore. Also, the beautiful Roman-style Castello di Velona hotel and spa is found perched atop a hill near Montalcino. They have a sophisticated restaurant and a relaxing spa (best for an excursion without the kids).

Where to Eat

The dining experience in Southern Tuscany is one to be treasured. There are countless amazing options, and almost any pizza stand on a corner will serve to delight the palate.

Please contact us to access our ever-expanding list of favorite eateries around town.


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