Southern Tuscany

Southern Tuscany

Things to do - general

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.

Cortona

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.

Montalcino

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 a hour, maybe longer if you stop to linger, which you definitely should.

Near Montalcino

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.

 

Casa Azzurra

Casa Azzurra

Chianciano Terme, Southern Tuscany
Tuscan farmhouseChianciano Terme 5 bedrooms, 5 bathrooms Sleeps 10 €3,570 – €5,000/week Rental perio More info
Casa Carina

Casa Carina

Chianciano Terme, Southern Tuscany
Private VillaChianciano Terme 4 bedrooms, 5 bathrooms Sleeps 8 €3,450 – €4,500/week This charming ho More info
Casa dei Giardini

Casa dei Giardini

Chianciano Terme, Southern Tuscany
Casa dei Giardini Luxury VillaChianciano Terme 11 bedrooms, 8 1/2 bathrooms Sleeps 20 €19,000/week R More info
Casa del Cortile

Casa del Cortile

Chianciano Terme, Southern Tuscany
Luxury Estate Chianciano Terme 7 units, may be rented together or separately Sleeps 2-32 €17,120 – € More info
Casa del Sole

Casa del Sole

Cortona, Southern Tuscany
Luxury Villa Cortona 10 bedrooms, 10 bathrooms Sleeps 20 €14,000 – €24,000/week Rental period: More info
Casa di Loggia

Casa di Loggia

Monticiano, Southern Tuscany
Casa di Loggia Tuscan FarmhouseMonticiano 9 bedrooms, 9 bathroomsSleeps 18 €7,750 – €8,150/week Rent More info
Casa di Pietra

Casa di Pietra

Chianciano Terme, Southern Tuscany
Private Villa Chianciano Terme 7 bedrooms, 6 bathrooms Sleeps 14 €4,750 – €6,200/week Rental period More info
Casa di Viti Rossi

Casa di Viti Rossi

Chianciano Terme, Southern Tuscany
Private VillaChianciano Terme 5 bedrooms, 4 bathrooms Sleeps 10 €4,100 – €5,650/week This beautiful More info
La Bandita

La Bandita

Pienza, Southern Tuscany
Farmhouse B & B Pienza 8 bedrooms, may be rented together or separately Sleeps 2-16 Per room €19 More info