Monticchiello, located in beautiful Tuscany, should be on your bucket list. Head here to see the world-famous rolling hills of Tuscany and frescoes dating back to the 14th and 15th centuries. 

Monticchiello is in the heart of the Val d’Orcia, known for being a historic medieval town where you can enjoy its beauty without the crowds. Thankfully, Monticchiello is off of the itinerary for many, being one of Italy’s best-kept secrets. If you’re a fan of live theater, you won’t want to miss their open-air performance space. 

Read on to discover why Monticchiello should be at the top of your list and how it’ll wow and delight you for years to come!

Welcome To Monticchiello – How to get there

You don’t want to make the mistake of thinking this beautiful town is hard to get to; quite the opposite! You’ll travel by car through the rolling hills of Tuscany, allowing you a scenic drive.

To get there

  • By air: The closest airport is Perugia (PEG). 
  • By train: There’s a train from the Roma Termini to Chiusi-Chianciano.
  • A third option is by car: From Florence, it’s only about a 1 hour and 24-minute drive. From north A1 to the Valdichiana exit, continue on SP327 toward Torrita di Siena. Then, SP 135 and SP 17 to Montepulciano. Head toward Monticchiello/Chianciano until the turn on SP88.

What To Do And Visit In Monticchiello, Italy

Nestled in the rolling hills, you won’t want to miss the “Poor Theater of Monticchiello.” In the town center, the area turns into an open-air performance space. 

In the upper part of town, head to the Torre del Cassero (Tower of Cassero). This tower overlooks the entire Valdichiana Valley and still has its medieval defense structure. 

The historical center of the town is filled with buildings from the 14th and 15th centuries. Take some pictures before heading to the Parish Church of Saint Leonardo and Cristoforo.

Where To Stay: Best Hotels In Monticchielo

While small, there are still plenty of beautiful homes and hotels to relax and enjoy the relaxing scenery. All you’ll need to consider is the location. 

A Beautiful View of Val d’Orcia

Bricks house during sunny day at the Azienda Agricola Barbi

The Azienda Agricola Barbi is only 5 miles from the town of Pienza. It’s two stone farmhouses with original features. 

Location: Podere Montello 26, 53026 Monticchiello, Italy

Stars: 3

Features: Pet-friendly, Free parking, Facilities for disabled guests

Reviews: 9.3/10

A 17th-century Beauty with A Pool

Stunning view from the large pool at the Agriturismo Le Macchie

Agriturismo Le Macchie. Enjoy stunning views of the surrounding valley as you dip in the large pool. Afterward, dry off and enjoy fresh wheat and olive oil grown on-site. 

Location: Via Della Montagna, 53024 Monticchiello, Italy 

Stars: 4

Features: Outdoor swimming pool, Air conditioning, Bathtub

Reviews: 9.4/10

Be A Part of History

Affittacamere Maria Gabriella offers rustic apartments and rooms with free Wi-Fi. You’ll only be 4.3 miles from Montepulciano. Relax as you take in views of the property garden and surrounding hills. 

Location: Via Marino Cappelli 6, 53026 Monticchiello, Italy

Stars: 3

Features: Free parking, Free WI-FI, Family Rooms

Reviews: 9.5/10

The Best Restaurants In Monticchiello, Tuscany

Daria Restaurant 

Highly-rated Daria restaurant combines Tuscan cuisine with innovation. So sit back and savor their various Tuscan wines with unique dishes created by their creative chef. 

Official Website: Daria Restorante

Location: Via S. Luigi, 3, 53026 Monticchiello SI

Reviews: 4.6/5

Insider Tip: Delicious Pici Dish

Osteria la Porta 

This tavern is located near the entrance door of Monticchiello. Savor regional and delicious dinners with beef, pork, and even vegetarian specialties. 

Official Website: Osteria la Porta 

Location: Via del Piano, 1, 53026 Monticchiello SI

Reviews: 4.4/5

Insider Tip: Best Meals and Wines

Osteria Fra Paolino 

Relax on the terrace at one of the highest-rated restaurants in Monticchiello. Their main dishes receive high marks, as well as their not to be missed desserts

Official Website: Osteria Fra Paolino

Location: Via di Mezzo, 17, 53026 Monticchiello SI

Reviews: 4.6/5

Insider Tip: Delicious Foods and Great Wines

Parking Area In Monticchiello

A scenic road near Monticchiello
Monticchiello is surrounded by trails and scenic roads

While the streets are too small for parking in the town center, there’s a convenient parking area. Drop off your car before a day of fun. The town is closed to general traffic, so you’ll need to park in the free designated parking area.

1. 406 Monticchiello Pienza

For one of the best hiking trails, head to 406 Monticchiello Pienza in Monticchiello, Tuscany. It’s a loop and an easy climb overall. 

2. Anello Monticchiello Pienza

This trail is moderate difficulty but is also a loop. The max elevation is about 1,664 feet. 

3. Buca del Beato

When you head to Monticchiello, Italy, include Buca del Beato on the list. It’s a one-way hiking trail of moderate difficulty. 

Places To See Nearby

The countryside between Monticchiello and Pienza
Pienza is the town we most recommend visiting nearby Monticchiello


In the province of Siena, you have Pienza. It’s between the towns of Montepulciano and Montalcino. It’s known as the “Touchstone of Renaissance Urbanism.” 


This Renaissance and medieval hill town will take your breath away. It’s also only 13 kilometers east of Pienza. 

Montepulciano is one of the best winemaking locations in the world! While sipping world-famous wine, relax and enjoy the views of the Tuscan countryside all around you. 

San Quirico D’Orcia 

The famous cypresses of San Quirico d’Orcia
The cypresses of San Quirico d’Orcia – a recommended photo spot

Only about 80 kilometers from Florence is this beautiful town. This historic village is in the center of Val d’Orcia.

This medieval town is surrounded by oak woods, vineyards, and olive groves. Its name comes from Saint Quiricus. San Quirico D’Orcia takes up a large space of Val d’Orcia. 

Don’t miss out on the Collegiate Church of Saints Quirico and Giulitta. It’s a Romanesque building that dates back as far back as the 8th century. This church has rare features dating back to the Lombard style in Tuscany.

Next to the Collegiate Church, walk to Palazzo Chigi, the town hall. Don’t miss out on the Church of San Francesco (also known as the Church of the Madonna).

Explore more: Southern Tuscany – Best Towns, Where to Stay, and Itineraries

Bagno Vignoni

Bagno Vignoni is unique since it has hot springs in the town center. Go for a swim in the warm springs believed to be healing by many Italians. The great news is it’s free! 

Feel like you’re traveling back in time since it was a healing place for many pilgrims. Many of those who would head to Rome would stop here on the way. 


Worth the trip, and not too far is the popular Siena, Italy. Don’t miss out on the artistic heritage and historic charm that you’ll see in this town. 

This ancient city is believed to date back to Etruscan times. If you love food, you’ll enjoy some of the tastiest and sweetest foods in Tuscany. Some popular dishes that’ll fill you up include Cinta Senese sausage, handmade Tuscan pasta (pici), and pecorino cheese.