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!

How to Get To Monticchiello

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.

5 Things To Do And Visit In Monticchiello, Italy

Here are some must-visit attractions and activities that showcase the essence of this picturesque village.

1. Belvedere

The beautiful panorama of Monticchiello seen from a Belvedere
Belvedere in Monticchiello – LigaDue, CC BY 3.0, via Wikimedia Commons

Monticchiello’s Belvedere is more than just a viewpoint; it’s a window to the soul of Tuscany. As you stand there, you’re embraced by the gentle Tuscan sun, with a panoramic view that stretches across rolling hills and lush vineyards. The Belvedere isn’t just a place to snap photos; it’s where you pause, breathe in the fresh air, and feel a deep connection to the picturesque landscape. It’s a moment of tranquility where the worries of the world seem to drift away, leaving you in a serene embrace with nature.

As the sun dips lower, casting a golden glow over the fields, the true magic of the Belvedere comes to life. The changing colors of the sky, from vibrant oranges to soft pinks, reflect the timeless beauty of Tuscany. Here, amidst the quiet, you find a rare peace that whispers of ancient stories and dreams yet to unfold.

2. Teatro Povero

The entrance to the Teatro Povero in Monticchiello
The Teatro Povero in Monticchiello – “MonticchielloTeatroPoveroPiazzaNuova” by LigaDue is licensed under CC BY 3.0.

Teatro Povero, or the ‘Poor Theatre,’ is a testament to the vibrant cultural spirit of Monticchiello. This isn’t your typical theatre experience. Here, the heart and soul of the community come alive on stage. The local residents, not professional actors, craft and perform plays that reflect their lives, histories, and traditions. It’s raw, authentic, and deeply moving. Watching a performance at Teatro Povero is like being invited into the homes and hearts of the locals, sharing in their joys, struggles, and stories.

The intimacy of the performances bridges the gap between audience and performer, creating a unique communal experience. As the narratives unfold, the passion and dedication of the people of Monticchiello illuminate the universal themes of life, making every spectator part of their extended family.

3. Pieve dei Santi

The main facade of Pieve dei Santi, in Monticchiello
The Church of Pieve dei Santi – “MonticchielloPieveLeonardoCristoforo” by LigaDue is licensed under CC BY 3.0.

The Pieve dei Santi Leonard and Christopher is a gem of religious and historical significance. This ancient church, with its simplistic yet profound architecture, invites a sense of peace and reverence. Its walls, steeped in history, tell tales of faith and time. Inside, you’re not just a visitor; you’re a pilgrim on a journey through time, where each stone and artwork whispers secrets of the past. It’s a place that commands a quiet awe, offering a spiritual retreat to those who walk through its venerable doors.

As you move through the hallowed aisles, the play of light through ancient stained glass paints the air with colors, further enriching the atmosphere of contemplation and spirituality. The echoes of centuries-old prayers seem to resonate within, connecting you to the countless souls who have sought solace and guidance here. In this sacred space, the present and the past converge, offering a profound experience of reflection and connection to the divine.

4. Walls and Entrance Door

Tourists are photographing the entrance to the historic town of Monticchiello, in Tuscany
The entrance door of Monticchiello – “Monticchiello (Pienza)” by Paolo Ramponi is licensed under CC BY-NC-SA 2.0.

The walls and entrance door of Monticchiello are like stepping through a portal to another era. These medieval fortifications, once built for protection, now stand as proud guardians of history. Walking through the entrance door, you can almost hear the echoes of the past – the clatter of horse hooves, the chatter of townsfolk. It’s a tangible connection to the centuries of lives and stories that have unfolded within these walls, a bridge from the present to the rich tapestry of history.

As you touch the ancient stones, you feel the weight of time, a solemn reminder of the enduring strength and resilience of this community. Each crevice and mark on the stone tells a story of survival, of battles fought and peace won. This is not just an entryway but a passage through time, where every visitor becomes a part of Monticchiello’s ongoing story, woven into the fabric of its remarkable history.

5. Cypress Road

The scenic view of the cypress road, in Monticchiello
The Scenic Cypress Road – “Monticchiello” by mirella bruni is licensed under CC BY-NC 2.0.

The Cypress Road in Monticelli is a journey, not just a route. Lined with the iconic Tuscan cypress trees, this road is a living postcard. Each bend brings a new vista, a fresh perspective of the Tuscan landscape. It’s a path that invites leisurely strolls or contemplative drives, where the beauty of the countryside unfolds in a rhythmic, almost poetic sequence. The Cypress Road is not just a way to get from one place to another; it’s an experience, a celebration of the serene and timeless beauty of Tuscany.

As you traverse this picturesque thoroughfare, the scent of the surrounding fields and the whisper of the wind through the cypress leaves accompany your journey, enhancing the sense of tranquility and connection with nature. Here, the world seems to slow down, allowing you to savor each moment and every detail of the stunning scenery that surrounds you.

More Things to Do in Monticchiello

These aspects of Monticchiello beautifully intertwine to create a tapestry of cultural richness, natural beauty, and historical depth, making it a must-visit destination for those seeking an authentic Tuscan experience. Here you can check out the experiences we recommend.

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
Photo Credit: – Agriturismo 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
Photo Credit: – 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

Apartment with beautiful garden in Affittacamere Maria Gabriella
Photo Credit: – Affittacamere Maria Gabriella

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

Here are the restaurants where I recommend you go to eat

Daria Restaurant 

Delicious dish with beautiful plating made in Daria Restaurant
Photo Credit: 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 

Inside the Osteria la Porta
Photo Credit: 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.

Here are three trails that offer a delightful mix of scenic beauty, challenge, and immersion in nature.

1. 406 Monticchiello Pienza

The 406 Monticchiello Pienza trail is a picturesque loop that embodies the essence of Tuscany’s countryside. As an easy climb, it’s perfect for beginners or those looking for a leisurely hike. The trail meanders through rolling hills, offering stunning views of olive groves, vineyards, and the distant silhouettes of medieval towns. The path is well-marked and takes you through a variety of landscapes, including rustic farmhouses and vibrant fields, making it an ideal hike for photographers and nature lovers alike. The gentle inclines and declines provide just enough variation to keep the hike interesting without being overly strenuous.

2. Anello Monticchiello Pienza

Anello Monticchiello Pienza is a moderately challenging loop trail that offers a more rigorous hiking experience. With a maximum elevation of approximately 1,664 feet, it presents hikers with rewarding panoramic views of the Val d’Orcia, a UNESCO World Heritage site known for its quintessential Tuscan landscapes. This trail is perfect for those who want to push themselves a bit further, with varied terrain that includes both flat stretches and steeper sections. As you ascend, you’re treated to breathtaking vistas of the surrounding countryside, dotted with cypress trees and ancient farmsteads. The trail also passes close to historic sites, offering a unique blend of natural beauty and cultural heritage.

3. Buca del Beato

Buca del Beato is a captivating one-way trail that strikes a balance between ease and challenge. It’s classified as moderately difficult, making it suitable for hikers with some experience or those looking for an adventure. The trail leads through diverse landscapes, including dense woodlands and open fields, offering a sense of seclusion and tranquility. Along the way, hikers can witness the local wildlife and the rich flora of the region. The path also features some elevation changes, providing a good workout and opportunities to stop and admire the enchanting views of Monticchiello and its surroundings. This trail is ideal for those seeking an immersive outdoor experience in the heart of Tuscany.

To Summarize

Each of these trails near Monticchiello provides a unique way to explore the natural beauty and historical charm of Tuscany. Whether you’re a casual walker or an avid hiker, these paths promise unforgettable experiences in one of Italy’s most idyllic regions.

Places To See Near Monticchiello

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.

Conclusion: Is Monticchiello Worth a Visit?

Definitely! Monticchiello is absolutely worth a visit. It’s a charming slice of Tuscany, where every cobblestone and corner tells a story. With its stunning views, cozy eateries, and the warm, welcoming locals, it’s the perfect spot for anyone looking to experience the heart and soul of Italy.