2 Days In The Val d’Orcia Itinerary

Here’s my 2 day itinerary for visiting Italy’s stunning Val d’Orcia region.

The Val d’Orcia is a valley in the heart of Tuscany that’s a UNESCO World Heritage Site. It’s the perfect place to spend a weekend enjoying a breathtaking pastoral countryside.

The Val d’Orcia is a place where history meets beauty. The area offers up some of the most unspoiled iridescent scenery in Tuscany. It’s home to ochre and green rolling hills, hunter green pine woods, olive groves, and vineyards.

famous zig zag road near Monticchiello and La Foce
famous zig zag road near Monticchiello and La Foce

The Val d’Orcia is rich is hot springs. It’s home to some incredible walled hilltop towns. What it’s not home to is mobs of tourists.

The Val d’Orcia is famous for its depictions in Renaissance art and cinema. Parts of The Gladiator, The English Patient, Twilight New Moon, Romeo and Juliet, and Under the Tuscan Sun were filmed there.

What Is The Val d’Orcia?

The Val d’Orcia is a picturesque natural landscape that’s a UNESCO Heritage Site

It’s an austerely beautiful part of Tuscany, just southwest of the hill town of Montepulciano in the province of Siena. 

For perhaps the first time in Europe, during the Renaissance, the Val d’Orcia was deliberately developed with aesthetics in mind.

The uncultivated land was tilled, leaving small woods between plots of land. Cypress trees were planted, leading to great estates.

The area is scattered with farm houses and tiny villages. It’s a harmonious blend of nature and mankind.

If you visit in the spring, the fields are green and filled with poppies. In the summer, there are reams of sunflowers. In the fall, there are great rolls of hay scattered over golden fields, following the harvest.

landscapes in the Val d'Orcia
landscapes in the Val d’Orcia

Where Is The Val d’Orcia?

Val d’Orcia is a valley in the province of Siena in southern Tuscany. The region extends from Siena to Monte Amiata. It’s the perfect place to take a weekend road trip.

The Val d’Orcia includes the towns of Volterra, Montalcino, Montepulciano, Montichiello, San Quirico d’Orcia, Bagno Vignoni, and Pienza.

How To Get To The Val d’Orcia

By far, the easiest way to tour the Val d’Orcia is by car. You could road trip there from Siena (45 minutes), Florence (1.5 hours), Umbria (1 hour), or even from Rome (2:15 hours).

If you’re coming from the north, you should take the road through Crete Senesi. It’s a moon-like landscape made of hill after hill of freshly plowed clay.

 landscape of the Val d’Orcia, the perfect weekend escape in Tuscany
landscape of the Val d’Orcia

Where To Stay In The Val d’Orcia

If you’re only in the Val d’Orcia for 2 days or a weekend, I would pick somewhere central to stay. The best spot is probably in or near Pienza. But you can also stay in a couple different places for variety.

Driving distances are close, so you can just pick something that appeals to you.

Some lovely hotels and resorts in the region include:

cypress lined path to Palazzo Massaini near Pienza
cypress lined path to Palazzo Massaini near Pienza

2 Days In The Val d’Orcia Itinerary

Here’s how to spend the perfect weekend or two days in the beautiful Val d’Orcia, pottering around its adorable hill towns.

As with all of my suggested itineraries, I recommend that you use this Val d’Orcia itinerary as a guide. You can tailor it to suit your individual interests, needs, and pace of travel. 

Day 1 Of Val d’Orcia Itinerary

On day 1 on your weekend in the Val d’Orcia, you can visit the towns of Buonconvento, San Quirico d’Orcia, Montalcino, Bagno Vigoni, and/or Bagni San Filippo. They’re all fairly small and clustered close together.

But, still, you should start early, to see all the highlights. If it seems too busy, you can always eliminate a stop.

main street in Buonconvento
main street in Buonconvento


Your first point of call is Buonconvento. The town is only 18 miles south of Siena and 62 miles from Florence. Its name derives from the Latin word for “happy gathering place.”

The town is famous for receiving a visit from Barack Obama in 2017.

Buonconvento is a small walled hamlet considered among the most beautiful villages in Italy. The main street is Via Soccini. There, you’ll find most of the town’s famous buildings, including the Palazzo Podestarile and the Palazzo Communale.

You should check out the Church of St. Peter and St Paul. It dates from the 14th century, but was “Baroque-ified.” The most valuable works from the church are now in the town’s Museum of Sacred Art.

For some folk history, you can pop into the Museo della Mezzzadria Senese, which shares tells the story of the region’s agriculture.

cityscape of Montalcino, a must visit town with 2 days in the Val d'Orcia
cityscape of Montalcino


The beautiful town of Montalcino is just 15 minutes down the road from Buonconvento.

Montalcino is a pretty village of medieval perfection. It’s crowned by a fairytale castle, blessed with magnificent views, and edged with vineyards. 

The town is known for its Brunello wine, one of the world’s most beloved reds. While in Montalcino, you can have a wine tasting and lunch at a medieval castle or take a 3 hour tour of the Brunello vineyards.

narrow street in Montalcino with a view of the fortress
narrow street in Montalcino with a view of the fortress

Montalcino’s historic center has barely changed in centuries. The main square is the Piazza del Popolo, with a Gothic loggia and clock tower.

The town is dominated by the mighty and imposing Rocca fortress. It was built in 1361 when Montalcino was captured from Florence by Siena.

From the ramparts, you’ll have spectacular views. The fortress also has a tasting room for oenophiles.

From Montalcino, it’s just 6 miles down the road to the Abbey of Sant’Antimo.

It’s a beautiful Romanesque building set amidst vineyards and cypresses. The 13th century abbey was likely founded by Charlemagne in the 9th century. If you are lucky, you can listen to the monks’ Gregorian chants.

San Quirico d'Orcia
San Quirico d’Orcia

San Quirico d’Orcia

Your next stop is San Quirico d’Orcia, just 17 minutes down the road. On the way to San Quirico, you can visit the Chapel of Our Lady of Vitaleta.

It’s an austere and isolated landmark in the Val d’Orcia. You can spot the chapel from the scenic drive along SP146.

San Quirico is a tiny hilltop village that was built along the Via Francigena. The town is famous for its food and wine traditions.

Chapel of Our Lady of Vitaleta
Chapel of Our Lady of Vitaleta

The village center of San Quirico is completely pedestrianized. The town is dotted with Romanesque churches. It’s so quaint you may want to move right in.

The top attraction is the magnificent Collegiate Church of San Quirico and Giulitta. It’s an outstanding 12th century Romanesque church right off the Piazza Chigi.

At the back of the Collegiate is the Palazzo Chigi. The pretty pink palazzo with 17th century frescos serves as the town hall. This is also where you’ll find the tourist office.

Bagno Vigoni
Bagno Vigoni

Bagno Vigoni

Bagni Vigoni is a tiny slip of a village situated on a hill just 10 minutes from San Quirico. The village is famous for its main square, the Piazza delle Sorgenti.

Except it’s not a square exactly. Rather, it’s a large open pool, which bubbles with waters from sulfurous hot springs below.

The Romans bathed here, as did the Medici. Pope Pius II came here from Pienza. The Medici built the Renaissance arcade surrounding the spring.

geothermal pool and hot spring in Bagni San Filippo
geothermal pool and hot spring in Bagni San Filippo

Bagni San Fillipo

If you have any time left in your day or skipped Bagno Vigoni, head a bit further south for a thermal spa soak in Bagni San Fillipo.

Like Bagno Vigoni, the village developed around a main square with a vast hot water pool. But, today, you can only admire it and can’t hop in for a swim.

But the town is home to other natural thermal springs. They’re rich in minerals and make for a perfect spa day. Because of the minerals, the water has a white-blue color.

The limestone waterfall (nicknamed the “White Whale”) and hot pools are surrounded by forests. The springs are completely free to visit. 

pretty lane in Pienza, a must visit town with a weekend in the Val d'Orcia

Day 2 Of Val d’Orcia Itinerary

On day 2 in the Val d’Orcia, you’ll visit the towns of Pienza, Montichiello, and Montepulciano.


Pienza is an adorable town known for its Renaissance architecture and pecorino cheeses. You should park outside the main gate.

Pienza was the first “ideal Renaissance town.” Pope Pius II transformed his birthplace into a town consistent with the principles of architecture set out in the treatise by famed architect Leon Battista Alberti.

The result is a classical set of monumental buildings that include the splendid Piazza Pio II, the Duomo, and the Palazzo Piccolomini.

pretty lane in Pienza, a must visit with a weekend in the Val d'Orcia

The Piccolomini Palace was the domestic summer residence of the Piccolomini family. Its spacious loggias face the countryside and look out over the first “hanging garden” to be laid out since antiquity. 

The palace is so beautiful that it was used by Zeffirelli in filming Romeo and Juliet.

Also make sure to walk around the panoramic walkway, Passeggiata Panoramica, behind the cathedral to enjoy fabulous views of the Val d’Orcia.

You’ll find artisanal pecorino cheese shops all over the town. Some Pecorinos are young and buttery, while others are sharper and aged up to a year. I advise taking home a “stagianato” pecorino (sharp zesty flavor).

If you want to grab lunch in Pienza, check out Trattoria Latte di Luna, Osteria Baccus, or La Terrazzo del Chiostro Restaurant.

pretty street with flowers in Monticchiello


Monticchiello is a tiny hamlet that’s a classic Tuscan village. It’s right between Pienza and Montepulciano. Monticchiello lies along a dusty road meandering between golden rolling hills.

It’s a tiny village of just 200 residents, with eye catching ruins of the city walls and towers that date from the 13th century.

The town’s most impressive building is its church, the Pieve dei Santi Leonardo e Cristoforo. The church dates back to the 1200s and has a plain yet beautiful Romanesque-Gothic facade.

The other thing not to miss in the Monticchiello is the panoramic view just outside the main medieval gate. From there, you can see the neighboring town of Pienza.

If you didn’t eat in Pienza, stop in for lunch at La Porta for some wine and tagliatelle with white truffles.

wine cellar in Montepulciano
wine cellar in Montepulciano


Montepulciano is a must visit town with a weekend in the Val d’Orcia. It’s an enchanting medieval village famous for its velvety vino nobile red wine. It’s the one town that’s a bit of a tourist magnet in the Val d’Orcia.

But you don’t have to be a wine lover to visit Montepulciano. The town is utterly beautiful and synonymous with most peoples’ images of Tuscany.

It’s perched on a limestone ridge and draped in vineyards. The town has ochre and rust homes set on streets paved with slate blocks.

Montepulciano boasts Renaissance palazzi and churches of a splendor far beyond its dimensions. Its architectural beauty led Montepulciano to be dubbed the “Pearl of the 1500s.”

Old streets in the Tuscan town of Montepulciano, Italy

There are plenty of amazing things to do in Montepulciano. If you haven’t been to Montepulciano before, you may want to book a guided walking tour to get the lay of the land. 

If not, the first thing to do in Montepulciano is stroll the pretty main drag, Il Corso. The street is filled with cafes, shops, and grand facades of Renaissance and Baroque palazzi.

Piazza Grande is the monumental center of Montepulciano. It contains all of Montepulciano’s most important Medieval and Renaissanace architecture — a clock tower, the Duomo, Palazzo Contucci, and a beautiful well.

Il Corso in Montepulciano
Il Corso in Montepulciano

Next visit Palazzo Communale, which is Montepulciano’s town hall. Plan on climbing the palace’s tower.

It’s a steep climb, but it’s worth the effort for the amazing panoramic views over the town, Piazza Grande, and countryside.

Il Corso is just one loop of a street in a thin town. But if you head down an alley, it’s hard not to gasp. The buildings frame a stunning vista and the lanes end in lookout parapets.

The last thing to see in Montepulciano is the stunning San Biagio Church. It’s one of the most beautiful Renaissance churches in Italy.

the beautiful Renaissance Church of San Biagio
the beautiful Renaissance Church of San Biagio

The impressive church is the masterpiece of Anthonio da Sangallo the Elder. It’s stacked up against the hillside above.

La Foce

Round off your Val d’Orcia itinerary with a visit to La Foce. It’s just 20 minutes from Montepulciano.

It’s worth the slight detour for the glorious views from its perch overlooking the Val d’Orcia.

It’s a completely renovated villa with a beautiful terraced rose garden and wisteria pergola.

You may want to stop for dinner here. La Foce has a restaurant serving up unique takes on traditional Tuscan cuisine.



Alternatively, head to the enchanting off the beaten track village of Montefollonico. It’s a tiny walled hamlet just 15 minutes north of Montepulciano. It boasts flower filled courtyards and a beautiful view of the valley.

In Montefollonico, you won’t find any tourists. One reason to visit aside from the authentic vibe? It has some fantastic restaurants for dinner to end your day.

La Chuisa has a Michelin-starred restaurant. Another great option that the locals love is Ristorante 13 Gubbo. You can dine in a medieval setting in one of the best restaurants in Tuscany.

landscape in the Val d'Orcia
landscape in the Val d’Orcia

Guided Tours To The Val d’Orcia

Don’t want to do the driving yourself? No problem, you can take guided tours to the Val d’Orcia from Italy’s major cities. You can:

Things To Do In The Val d’Orcia

Aside from all the quaint towns I’ve mentioned above, there are some classic activities to indulge in the Val d’Orcia:

Piazza della Repubblica in Cortona
Piazza della Repubblica in Cortona

More Time In The Val d’Orcia?

If you have more than a weekend or 2 days in the Val d’Orcia, spend another day in the town of Cortona and Lake Trasimeno in Umbria.


Buttressed against Monte Sant-Egidio, at a height of 2,000 feet, Cortona has the broadest panorama of any hill town in Tuscany.

Cortona was made famous by the movie and book Under The Tuscan Sun. It’s a quiet stony charmer.

Cortona’s main street is Via Nazionale, the only flat place in town. At one end of the street is Cortona’s most famous piazza, the Piazza della Repubblica, perfect for lunch and people watching. At the other lies the splendid Piazza Garibaldi.

Cortona has a wonderful little museum you’ll want to visit, the Museo Diocesano. The museum has some absolutely superb paintings — works by such Renaissance luminaries as Far Angelico and Luca Signorelli.

You can grab some lunch at Osteria al Teatro or Ristorante La Loggetta.

Lake Trasimeno and the town of Passignano sul Trasimeno
Lake Trasimeno and the town of Passignano sul Trasimeno

Lake Trasimeno

Lake Trasimeno is right on the edge of Tuscany and Umbria, and technically in Umbria. It’s just 20-25 minutes from Cortona.

The lake is dotted with tiny hamlets and has three islands. It’s the perfect place to relax and go swimming, boating, or biking. You can also hop a ferry to explore the island of Isola Maggiore.

I hope you’ve enjoyed my guide to spending the perfect 2 day weekend in the Val d’Orcia. You may enjoy these other Tuscany travel guides and resources:

If you’d like to spend 2 days in the Val d’Orcia, pin it for later.

Pinterest pin for spending 2 days in the Val d'Orcia

Leave a Comment