The Small Towns You Can't Miss in Southern Tuscany

Tuscany covers a large area of the Italian countryside and there are so many different areas to choose from. The Chianti region--the area between Florence and Siena (read about it here)--is one of the most popular maybe because of its proximity to Florence, maybe because of the shear number of quaint medieval hill towns or maybe because of the delicious, drinkable wine. But there are other wonderful areas to check out too.

For our 1 year anniversary, my husband and I decided to visit a part of this beautiful region that we had never been to (and did not get a chance to visit during our busy wedding week). So after a few days eating our way through Emilia Romagna, we made our way down to the area south of Siena to learn about Brunello & Vino Nobile, take a road trip through the picturesque Val d'Orcia and to relax in a cozy farmhouse. I recommend visiting this area especially if you're into wine because some of the best in Italy is found here but I also recommend visiting this area to simply relax and admire the views. NOTE: A car is needed to explore this area but don't worry, the roads are not nearly as busy and hectic as they are in Florence or Rome!

WHAT TO SEE & DO

VAL D'ORCIA

Val d'Orcia

Val d'Orcia

This UNESCO World Heritage Site is a must-see for its green rolling hills, cypress-lined roads, vineyards and old medieval hill top towns and castles. Hit the road for these towns in particular and keep your camera ready at all times.   

MONTALCINO - The main star of this little town is the wine (more on that below), but the boutique shopping is great too. Be sure to check out family-run shop Sartoria Principe (Piazza del Popolo, 2) for some stylish casual-wear and quality table linens made on the premises. Also family-run Montalcino 564 (Piazza del Popolo, 36) is a lovely little shop stocked with fine perfumes and soaps and linens for the home. Before you leave, make sure you wander the outskirts of town along the walls for some breathtaking views.

Piazza del Popolo, Montalcino

Piazza del Popolo, Montalcino

A beautiful view from Montalcino

A beautiful view from Montalcino

PIENZA - Perhaps my favorite of them all if I had to decide. Quite small but with a cuteness factor of 100+. Stop for a few gorgeous photos along the Belvedere lookout point overlooking the valley and then grab a traditional Tuscan lunch at Trattoria Latte di Luna (Via San Carlo, 2/4). You won't be disappointed.

A vintage Fiat 500 parked in Pienza

A vintage Fiat 500 parked in Pienza

The streets of Pienza

The streets of Pienza

Quaint bar in Pienza

Quaint bar in Pienza

MONTEPULCIANO - An inviting medieval town with lots of cute shops and cafes. I recommend relaxing in Piazza Grande with a glass of wine (more on that below) as you watch the world go by. Before continuing on to the next adorable town on your itinerary, stop at Caffe Poliziano (Via Voltaia del Corso, 27/29) for an espresso in an old, elegant coffee shop. If you're not in a hurry try to snag a spot on the terrace in the back for some nice views.

Piazza Grande, Montepulciano

Piazza Grande, Montepulciano

MONTICCHIELLO - The tiniest of the towns but all the more reason to visit. The views overlooking the valley are spectacular and the cobblestone streets are super charming. For an amazing meal, make a reservation at Osteria La Porta (Via del Piano, 3) for dinner. The bistecca alla fiorentina served with a fresh, green salad and cannellini beans was possibly the best meal I've ever had in Italy. So simple, yet so delicious. 

The breathtaking view from Monticchiello

The breathtaking view from Monticchiello

CORTONA

Located about 45 min Northeast of Montepulciano is this medieval town where Under the Tuscan Sun took place. Stroll the quaint cobblestone streets and take in some fantastic views of the countryside and nearby Lake Trasimeno from the town walls. Fill your bellies with some yummy local specialties in an old wine cellar at Ristorante La Bucaccia (Via Ghibellina, 17). If the owner likes you, he will give you a shot of grappa on your way out (yikes!)

Piazza della Repubblica, Cortona

Piazza della Repubblica, Cortona

The bell tower in Cortona

The bell tower in Cortona

A small Cortonese street

A small Cortonese street

DRINK SOME LOCAL WINE

  • Brunello di Montalcino DOCG - One of Italy's most well-known, highly-rated and expensive wines made from 100% Sangiovese grapes and aged for 2 years in Oak barrels followed by at least 4 months in the bottle. A great way to taste and buy some is to stop into one of the wine shops in town or if you have a bit more time, visit one of the wineries on the road into town. Be sure to pick up a few bottles, since this stuff back home costs a pretty penny.
  • Vino Nobile di Montepulciano DOCG - Not to be confused with Montepulciano d'Abruzzo, this prestigious wine is a blend of mostly Sangiovese grapes with some other local varietals. It's aged for at least 2 years, 1 of which in oak barrels. A great place to try and buy is at the historical winery in town, Cantina Contucci (Via del Teatro, 1), or at the impressive Avignonesi Estate (Via Colonica, 1, Valiano di Montepulciano) located 20 min outside of town. Be sure to try a riserva as well, which has been aged a bit longer, it's quite delicious!
Vino Nobile di Montepulciano at Cantina Contucci

Vino Nobile di Montepulciano at Cantina Contucci

WHERE TO STAY

This area is chock full of charming old farmhouses and villas that have been restored and turned into beautiful inns and hotels. Here are my favorites all of which are strategically located in the Val d'Orcia making it easy to get to all of the towns above.

  • Poggio Piglia - A favorite of mine perhaps because of the friendly and hospitable innkeeper, Paolo. But the rustic yet modern decor (those wood-beamed ceilings!) and spacious bathrooms, some with soaking tubs overlooking the hills outside, was pretty amazing too. A delish onsite restaurant with a lovely outdoor terrace (and chocolate cake you dream about) and a refreshing infinity pool with a view make you never want to go home. Starting around $200/nt. (Macciano, SI)
  • Villa Armena - A rustic boutique property with traditional yet luxurious decor and modern bathrooms with soaking tubs. An onsite restaurant, wine cellar and free-form pool make this another solid choice. Rumor has it the house dog is super cute too. Starting around $200/nt. (Buonconvento, SI)    
  • Follonico - A very small, old farmhouse with cozy, rustic decor. What it lacks in amenities (no restaurant or pool), it makes up for in charm. Guests can expect breakfast though, with freshly-baked, locally-sourced goods. And the view is to die for. Starting around $250/nt. (Localit√† Casale 2, Torrita di Siena, SI) 
  • La Bandita - For a bit of a splurge, go for this stylish spot with a stunning infinity pool in a remote location outside of Pienza. No restaurant but locally-sourced breakfasts served daily. If you'd prefer being closer to town and having a restaurant, check out sister property La Bandita Townhouse. Both starting around $350/nt. (La Bandita: Localita Podere Lucia 14, Pienza, SI; Townhouse: Corso il Rossellino 111, Pienza, SI)
Luxury farmhouse accommodations at Poggio Piglia

Luxury farmhouse accommodations at Poggio Piglia

Aperitivo on the terrace, Poggio Piglia

Aperitivo on the terrace, Poggio Piglia

The driveway to Poggio Piglia

The driveway to Poggio Piglia

Lastly, this is definitely one of those trips that you will need to leave some room in your suitcase. The wine is just too delicious not to bring home. Tip: I love packing a foldable nylon weekend bag (like a Bric's on Longchamp) and then using it for clothes on the way home so the wine can fit in the suitcase! Sometimes, if you're lucky, the airline won't even charge you to check it which is an added bonus. Another tip: Amazon sells these wonderful sleeves for your wine that are lined with bubble wrap and they seal at the top so your clothes don't get ruined if a bottle breaks. Ciao for now!

Cam and me taking in the view of the Tuscan countryside

Cam and me taking in the view of the Tuscan countryside

A sunset over Tuscany

A sunset over Tuscany