Monticchiello (Italy) – My Guide to the Southern Tuscan Treasure

Are you visiting the Val d’Orcia and wondering if Monticchiello deserves some of your precious vacation time?

Maybe you’re in neighboring Montepulciano and loving it – but are craving a visit to a ‘real’ Tuscan village that isn’t full of souvenir shops.

Either way – Monticchiello is worthy of a visit.

I’ll admit it – I drive by Monticchiello often on visits to other treasures in Southern Tuscany’s Val d’Orcia. But, every time I do stop in, I’m glad I did. On each visit, I’m rewarded with epic countryside views, a quiet and beautiful small village, and friendly locals.

I recently stopped in and I want to share some of my favorite parts of Monticchiello with you. These are things I do with my kids and visiting friends and family.

Note: I’ve been working, traveling, and living in Italy for over two decades. Tuscany is my home – let me share this part of it with you!

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Table of Contents

Why Visit Monticchiello?

Front entrance and archway of village of Monticchiello in Italy. Man walking through arch and cyclist riding down towards us. — This is ‘traffic’ in Monticchiello

True – powerhouse Tuscan villages Montepulciano and Pienza are just a stone’s throw away. But, Monticchiello is an authentic, tiny village of just a couple hundred residents.

Monticchiello is the type of place you’ll ‘ooh and ahh’ over the doorways decorated with plants and flowers, smile at the panoramic view of Pienza over a glass of red wine, and eat some of the best pasta of your trip.

Skip a visit to Monticchiello if you’re looking for a lively atmosphere, lots of cultural sites and monuments, or a place to go shopping.

Before we get into the details, are you wondering if you’re butchering the pronunciation of Monticchiello?

Monticchiello is pronounced mohn-tee-kee-EL-loh. Yes, it’s a mouthful! Have no fear – just listen to this audio of the correct pronunciation:

Where is Monticchiello?

Monticchiello is in the UNESCO World Heritage Site of the Val d’Orcia (Orcia Valley) in Southern Tuscany. It’s between the famous villages of Pienza (cheese!) and Montepulciano (wine!).

Distance between Monticchiello and:

City/Town	Distance (kilometers)	Driving Time
Pienza	10	15 min
Montepulciano	9	15-20 min
Siena	60	1 hr 10 min
Florence	115	1 hr 40 min
Rome	175	2 hr 10 min

You may want to check out my Guide to the Val d’Orcia

When to Visit Monticchiello

Monticchiello is at its best in the summer when you can watch a performance of the town’s outdoor theater and have dinner on a patio that spills into one of the village’s cobblestone streets. You’ll see the most visitors in the summer, and it’s when the village is most alive.

Spring and fall are also lovely, but I’d stick to late spring and early fall. Why? Because Monticchiello is really quiet in the winter – a little too quiet for me. Things close up and you’ll find yourself driving to Montepulciano for necessities and more options for meals.

The weather in Montichiello mimics the other Val d’Orcia towns. To simplify – hot summers (make time for exploring Monticchiello in the morning or evening), pleasant weather during the spring and fall (with occasional rain expected), and chilly winters (snow not likely).

Good To Know: If you find yourself in the area during the winter holidays, be sure to stop in Montepulciano for its Christmas market – one of our favorites in Tuscany.

Read more about visiting Tuscany in the Spring – Summer – Fall – Winter

What to See and Do in Monticchiello

Bright red vespa sits in front of a stone wall in Tuscany.

Bright yellow crocus flowers growing next to stone wall.

Monticchiello doesn’t have anything major to ‘check off your list.’ Instead, it’s a place to wander, admire the small cobblestone streets, take in the views of the Val d’Orcia, and enjoy some local food and wine.

These are my favorite things to do when I visit Monticchiello:

Walk the Old Walls

Gravel path leads toward a tall stone tower in a medieval village in Tuscany. On left you can see rolling hills of countryside fields and cypress trees. — I love the views on this walk along the edges of Monticchiello

You won’t be walking on anything as well-maintained as Monteriggioni’s walls or Capalbio’s walls, but you can go on a nice little stroll on a gravel path where they used to be. Still, the views of the surrounding countryside are lovely and you’ll likely have the path to yourself.

Enter the path to the left of Porta Sant’Agata (the main entrance to town). The path will finish (it’s closed off) before you get to the Rocca di Monticchiello (town fortress) – it spits you back into the village on a tiny cobblestone lane.

Good To Know: It takes 5-10 minutes to walk the path, depending on how often you stop to check out the view.

Admire the Tiny Piazzas and Lanes

Front of old stone building in Tuscany. Late afternoon light shines on the stone walls and the potted plants decorating the front entrance.

Small piazza with stone buildings. Flower pots decorate the steps and walls.

Like most small Tuscan villages, Monticchiello has its share of little cobblestone piazzas decorated with flowers and small narrow lanes asking for a wander.

You can cover the town in about 10 minutes, but you’ll likely take longer stopping for photos of the doorways and chats with neighborhood gatti (cats).

Catch a Performance of the Teatro Povero

The teatro povero (literally ‘poor theater’) is one of the most interesting and unique things about Monticchiello. I had a chance to sit down with Roberto, an older Monticchiello resident and extremely involved member of the teatro povero, who filled me in on the event.

The town (population: about 200) convenes each January just after the Befana to discuss ideas for the season’s performance. Once a decision is made on the theme, the work begins – on the script and everything else, including choosing the actors, designing sets, doing the marketing, and more.

One of the most amazing things (to me at least) about Montichiello’s teatro povero, is that everyone in the village gets involved – from little kids to farmers to nonni (grandfathers). While not everyone has a role on stage, everyone contributes to the success of the shows.

Speaking of the shows… If you want to see one, you’ll need to stop by Monticchiello in the summer. The performances typically run nightly for two weeks from the end of July through mid-August. You can buy your tickets at the door. Keep in mind that the performances are in Italian, but know that you’ll enjoy the experience – in the tiny Piazza Commenda that surrounds the town church.

Although I live nearby and stop in Monticchiello for a quick stroll or meal whenever we’re in the area, I’ve yet to see a performance of the teatro povero. Maybe I’ll see you there this upcoming summer!

Find the Winding Cypress-Lined Road

The best place to see the famous winding, cypress-lined road is from here, but you can also get a peek of it from the parking lot below town. It’s tough to see it from Monticchiello, so I recommend stopping at the spot mentioned above on your way out of town (or on your way in if you’re coming for dinner so it will be light enough to see).

If you want to peek at it while you’re in Monticchiello, you can see it from the parking lot or from the Giardino del Cassero near the old walls (that’s the viewpoint from the photo above).

Good To Know: You’ll also get amazing views of this road and the surrounding countryside if you stay the night at La Torre del Carlo on the edge of the village.

Find Your Favorite Viewpoint

View of Tuscan countryside. You can see Pienza on the hill in the background on the left. — Can you spot Pienza?

You’ll find lovely vistas in Montichiello – check out those rolling hills of the Val d’Orcia!

See if you can find Pienza in the distance.

My favorite viewpoints are the small panoramic terrace near the town entrance, and the views from along the gravel path of the old walls.

Good To Know: There’s a public toilet just below the panoramic terrace.

Have a Leisurely Meal

This is my favorite thing to do in Monticchiello. After a stroll around town, take a seat and enjoy classic Tuscan cuisine with local wines (I like Vino Nobile di Montepulciano and Rosso di Montepulciano – both from the next town over).

Good To Know: I’ve listed a few restaurants below, and you’ll need to decide if a view is important to you. Some of Monticchiello’s best restaurants are tucked in narrow village lanes, but you can always have a pre-dinner aperitivo with a view!

Where to Eat in Monticchiello

View of front entrance of Daria Ristorante in Monticchiello, Italy. Vines and plants decorate the entrance. You can see the red Michelin sign on the right as well as tables and chairs under a tent.

Ristorante Daria – Try the homemade pici pasta or one of the more creative dishes – either way, you won’t be disappointed. Ristorante Daria uses high-quality, local (whenever possible) ingredients. The setting is lovely too.

Good To Know: Sadly, chef and sommelier Daria passed away in 2021. Her daughters, Deborah and Giada have taken over and continue to provide the excellent service and warmth that their mother brought to the village.

L’Angolo di Daria – My pick for pre-dinner cocktails or a lazy afternoon aperitivo. Get an outdoor table.

Osteria Fra Paolino – Another excellent choice in tiny Monticchiello. Paolo serves up classic Tuscan dishes as well as more unique dishes.

La Guardiola Wine & Food – This place has a wonderful casual setting with lovely views. It’s just outside the walls (you’ll pass it as you walk up from the parking lot) and I find it to be the best place for an aperitivo. It’s a great mix of locals and visitors enjoying a spritz with a board of prosciutto and local pecorino cheeses.

Where to Sleep in Monticchiello

Wooden door in stone entrance to B&B La Casa di Adelina. Guidebook signs on right side of door and small plant to left of door. Old stone and brick walls. — Entrance to B&B La Casa di Adelina – you can walk right next door to Osteria Fra Paolino for dinner

B&B Daria – The perfect place to wind down and relax after a day of exploring the Val d’Orcia and its villages; private terrace and garden; you can rent a room or the villa; the B&B is connected to the two Daria restaurants in the center of Monticchiello.

Il Torrino – Another Daria property. This is a unique place to stay (honeymoon, romantic getaway, anniversary) – in a little tower at the edge of the village. Elegant, simple décor and epic views of the countryside.

B&B La Casa di Adelina – You’ll feel like you’re visiting the home of friends. Clean, comfortable rooms with attentive host Francesco.

If you’re visiting in the summer and need a swimming pool, look into staying at a nearby agriturismo like Agriturismo Terre di Nano.

Helpful Tip: If you’re visiting in the summer, ask if your accommodation has screens on the windows (pesky mosquitoes) or air-conditioning (summers are hot here!).

Good To Know: There’s a newer part of the village below. If you’re spending the night in Monticchiello, you want to be in the old (upper) village (north on the map).

Visiting Monticchiello with Kids

Children's playground with yellow slide and toys. Grassy area surrounded by tall cypress trees. Sunny day with blue sky.

Part of a fresco inside a church in Tuscany. You can see a knight kneeling and praying. Most of the fresco is destroyed and the rest of the wall is cream colored.

There’s not a ton to do in Monticchiello with kids but it’s an easy place to visit because you don’t have to worry about a lot of traffic (but cars can enter the village so always be aware). It makes for a nice stop on a day trip to the area from Florence with your kids.

If you’re visiting during the teatro povero, you could let your kids watch and see the local children performing.

The playground (just outside the walls) is small but fills up with local kids in the afternoon. It has swings, a small slide, spring toys, climbing ropes, and benches with some shade. You’ll see it as you walk up to town from the parking lot. As a bonus, La Guardiola is attached so you can sit at a table right next to the playground and have a cool drink or snack while your kids play (they can join too, of course).

You could bring a stroller into Monticchiello, but it’s easier to let little ones walk and explore – town is that tiny.

If you need groceries, diapers, or other baby products, you’ll need to get them from a nearby village. Pienza has a small Coop and Montepulciano has a larger Conad supermarket.

I find Monticchiello to be an easy place to eat with kids. I recommend eating outdoors at one of the restaurants so your kids can get up from the table to play if they finish early.

If you’re in town, check out the teatro povero. I’m going to try to bring my boys this coming summer, so maybe we’ll see you there! If you’re not in town during the performances, you can stop in at the quirky exhibit at the Teatro Povero center in Piazza Commenda (the part with the four large trees).

Be sure to walk along walls and up to the garden (Giardino del Cassero) to look at the art scattered around the trees. And in the church (Chiesa dei Santi Leonardo di Limoges e Cristoforo – Church of St. Leonard and St. Christopher), see the frescoes and find the knight.

How to Get to Monticchiello

Cypress trees line on the sides of a road in the Val d'Orcia in Tuscany, Italy — This is from a drive to Monticchiello in the winter

The best way (by far) to get to the medieval town of Monticchiello is with your own car.

Helpful Tip: A fun and scenic way to get to town is on the winding, cypress-lined SP88 that arrives in Monticchiello from the southeast. When you park you can get a nice view of it.

You can park your car in the gravel lot below town and walk up the hill for 150-200 meters to the entrance to the village. If you have kids/strollers or people in your group who would struggle with the uphill, you can drive your car up to the entrance and drop everyone off (there’s enough room to turn around). Just don’t drive through the arch and into the village because there’s a ZTL.

Good To Know: Google Maps shows a shorter route between Pienza and Monticchiello on this road, but know that it’s on gravel. It’s a beautiful road (I’ve driven on it, hiked it, and ridden my bike on it), but it can get dusty in the summer and you need to keep your speed under control.

Read more about Renting a Car in Tuscany

What to See and Do Near Monticchiello

Eat cheese in Pienza (and have gelato)
Sip Vino Nobile in Montepulciano (or venture a little further to Montalcino for Brunello di Montalcino)
Go for a walk or bike ride in the Val d’Orcia
Soak in the Bagno Vignoni hot springs or one of the other nearby Tuscan hot springs

Good To Know: I’m often asked if it’s worth visiting Monte Amiata (Southern Tuscany’s highest mountain). I’ve hiked on it and ridden my bike up (all routes). It’s wooded up top and there’s not much going on, so I wouldn’t recommend it for a hike. It’s a fun challenge to cycle to the top (worth it), but it’s not worth driving up (no views). It’s a good spot to collect chestnuts in the fall (if you have a place you can roast them).

I hope this helps you with your Monticchiello travels! And, if you like small villages and hamlets, some others in Tuscany you should check out include: