Ultimate Val d’Orcia Travel Guide: Where to Visit and What to Do

After a second long stay in Val d’Orcia, I’m sharing a personal guide on where to visit and what to do in this part of Tuscany. A special valley that cuts through between Montepulciano and Montalcino, Val d’Orcia is one of the best regions in Tuscany to explore.

For me, when I think of Tuscany, my mind pictures the Val d’Orcia. It’s a postcard-perfect area, rolling hills dotted with hilltop villages, and never-ending olive groves and vineyards. The Val d’Orcia is home to some of the best villages to base yourself and visit, from Pienza to Montalcino, dozens of amazing restaurants, and some very stand-out hotels to choose from.

It was my second time back to Val d’Orcia, and we spent nearly two weeks enjoying the slow pace that comes with Tuscany (see my Tuscany itinerary for how we organized our time). Traveling this time with our daughter, my husband and I spent days often with a walk through the countryside. It was always followed by a hearty lunch and, of course, a visit to a new village each day.

Val d’Orcia is a lovely region, whether you have a week or just a few nights, as there is a lot packed into one area. So I’m sharing my travel guide to Val d’Orcia, with all of the best things to do, where to eat, and stay.

Short on Time? Here Are My Top Picks for the Best Hotels and Things to Do in Val d’Orcia

Base yourself between Pienza and Montepulciano, or Pienza towards Montalcino for easy village-hopping.

Hotels

1. Lupaia ($$$$ / Where I Stayed), for a luxury boutique hideaway with incredible views and a standout restaurant
2. Rosewood Castiglion del Bosco ($$$$), for a classic Tuscan resort with vineyards, spa, and golf
3. Casa Newton ($$$), for a chic design-forward stay in the countryside
4. La Bandita Townhouse ($$), for a stylish in-village stay right in the heart of Pienza
5. La Fonte Agriturismo Agriristoro ($), for a simple, charming farmhouse stay surrounded by fields

Airbnbs

1. 2 Bedroom Garden Apartment near Pienza (Where I Stayed), for the best Val d’Orcia views
2. 2 Bedroom Historic Apartment in Pienza, for the best Pienza town-center rental
3. 2 Bedroom Apartment in Montepulciano, for the best panoramic city stay
4. Studio Loft in Montepulciano, for the best walkable historic rental
5. 2 Bedroom Panoramic Country Suite in Montalcino, for the best scenic Val d’Orcia base
6. 2 Bedroom House in Montalcino, for the best central Tuscan stay

Things to Do

1. Tuscan Cooking Class of Homemade Pastas and Cantucci Cookies — hands-on pasta and biscotti-making at Agriturismo Podere Spedalone near Pienza.
2. Montepulciano Private Pasta-Making Class — learn regional recipes in a local home in Montepulciano.
3. Wine and Wonders: Montepulciano Vineyards Tour — visit three estates, taste Brunello-style reds and Vino Nobile, and let someone else handle the driving.
4. Luck and Patience Truffle Hunt in Tuscany — join a truffle dog and guide in the woods near Montepulciano, then stay for a truffle-forward lunch.

Helpful Guides to Plan Your Trip

Planning a trip to Tuscany? Start with my Tuscany itinerary for a practical, day-by-day plan, then dive deeper with my guide to the best towns to base yourself in Tuscany, my in-depth guide to the best villages to stay in Tuscany, and my full guides to visiting San Gimignano, Siena, Pienza, Montepulciano, and Montalcino. If you’re also spending time in Florence, don’t miss my guide to the best things to do in Florence, my Florence itinerary, and my curated guide on where to stay in Florence!

Travel Tip: The best way to explore Tuscany is by driving yourself. We use Discover Cars for our rental cars in Europe, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt. Renting a car and driving in Tuscany is quite easy. Book your car with Discover Cars here.

The Val d’Orcia Travel Guide

---

Helpful Tips Before Planning Your Trip to the Val d’Orcia

Where is the Val d’Orcia?

The Val d’Orcia is a rolling valley in southern Tuscany, stretching between Montepulciano and Montalcino along the Orcia River. Geographically, it lies about 110 km south of Florence, positioned well within Tuscany’s rolling interior. It also sits roughly 180 km north of Rome, making it a midpoint landscape between the two major cities. It’s just beyond Siena and San Gimignano, and it’s my personal favorite part of the classic Tuscan countryside.

When is the Best Time to Visit the Val d’Orcia?

My experience with the Val d’Orcia is that the seasons do matter, as many hotels and even restaurants close for the winter. Most close December through the end of February, so I would opt to go when most things are open. I would try to avoid the peak hot summer months and look to go in the shoulder season of late spring or late fall. I’ve been in September and October, and these were lovely times to catch the fall harvest.

How Many Days are Enough to Visit the Val d’Orcia in Tuscany?

I feel like the ideal amount of time is 3-5 days, depending on your itinerary. You could easily spend a week-plus if using it as a base to explore other regions like Chianti, Umbria, and nearby cities like Siena and San Gimignano. My Tuscany itinerary outlines how I’d spend 7 days in the region.

What’s the Best Way to Get Around in the Val d’Orcia?

A car is absolutely a must for exploring the Val d’Orcia, as the small towns are best reached by car. Public transportation here is not ideal. I would recommend picking up a rental car in Florence or Rome and driving in.

Travel Tip: The best way to explore Tuscany is by driving yourself. We use Discover Cars for our rental cars in Europe, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt. Renting a car and driving in Tuscany is quite easy. Book your car with Discover Cars here.

---

Where to Stay in the Val d’Orcia

In my guide to the best villages to stay in Tuscany, I go into depth about the Val d’Orcia and where I’d pick. In short, I would pick somewhere between Pienza and Montepulciano, or Pienza towards Montalcino. I recommend picking a place you can easily come/go from, as you’ll be doing a lot of road tripping through the valley.

My Top Val d’Orcia Hotel Choices

• Lupaia ($$$$ / Where I Stayed), for the best luxury boutique hotel
• Rosewood Castiglion del Bosco ($$$$), for the best luxury resort in the Val d’Orcia region
• Castello Banfi – Il Borgo – Relais et Chateaux ($$$$), for the best historic luxury hotel
• Casa Newton ($$$), for the best new design hotel
• La Saracina ($$$), for the best boutique hotel with grand rooms
• Capanna Suites ($$$), for the best luxury agriturismo with a view
• La Bandita Townhouse ($$), for the best in-village stay in Pienza
• Stelle di Monte ($$), for the best luxury guesthouse stay
• Borgo Canalicchio Di Sopra Relais ($$), for the best romantic boutique hotel close to Montalcino
• Villa le Prata ($$), for the best winery hotel stay
• La Fonte Agriturismo Agriristoro ($), for the best farmhouse stay

My Top Airbnb Choices

• 2 Bedroom Garden Apartment near Pienza (Where I Stayed), for the best Val d’Orcia views
• 2 Bedroom Historic Apartment in Pienza, for the best Pienza town-center rental
• 2 Bedroom Apartment in Montepulciano, for the best panoramic city stay
• Studio Loft in Montepulciano, for the best walkable historic rental
• 2 Bedroom Panoramic Country Suite in Montalcino, for the best scenic Val d’Orcia base
• 2 Bedroom House in Montalcino, for the best central Tuscan stay

---

The Best Villages to See in the Val d’Orcia

Each village in the Val d’Orcia has its own rhythm, and after spending time exploring many of them, I’ve found the joy is in how different they feel from one another. Some are lively and full of cafés, others are quiet and wonderfully sleepy. These are the villages I think are most worth visiting.

Pienza

This small Renaissance town in Tuscany is my favorite village in Val d’Orcia. Pienza has lots to offer in terms of views, charm, and liveliness. You can easily see it in a day, but I’d make sure to book at least one meal in the historic town. Pope Pius II designed the village in the 15th century as his “ideal village,” and it’s easy to see why. For me, a perfect day here includes a late-morning stroll, stopping by Piazza Pio II, the cathedral, and Palazzo Piccolomini, a UNESCO World Heritage Site known for its perfectly proportioned architecture.

It’s also home to pecorino cheese, so if you smell a cheese shop or two, don’t hesitate to go in. You can try a few samples, and the best part is that the cheese can be vacuum sealed and brought back in your suitcase. And of course, there are a few standout meals you can’t miss. Go out of your way to eat at Sette Di Vino. It’s all things traditional Tuscan cuisine, where the bean soup and artichokes are the stars of the show.

Favorite Things in Pienza

• Try local products in shops like Salumeria Gastronomia del Corso Pienza, Marusco e Maria, and La Taverna del Pecorino
• Enjoy restaurants in town like Sette di Vino, the restaurant at La Bandita Townhouse Hotel, and PROSIT
• Enjoy the views from Via del Casello, adjacent to the Duomo di Santa Maria Assunta or Pienza Cathedral
• Visit the Diocesan Museum (Palazzo Borgia) and then stroll through the Piazza Pio II
• Go for a walk down the path to Panorama il Gladiatore Cosi Bella, an iconic dirt road from the gladiator movie, lined with cypress trees

Montalcino

Even after two separate day trips to Montalcino, I can’t put into words the charm of this thimble-sized village. It’s compact yet charming, with incredible views stretching over rolling vineyards. It’s also home to some of the best wine, the “Brunello di Montalcino,” some of the best in the Tuscan valley, all while feeling very authentically local.

For me, what makes Montalcino great is an afternoon arrival. Spend an hour or two wandering around the streets and shops, grab a glass of wine at one of the many wine bars, sample wines, and soak it all in. There are a handful of great restaurants as well, so arrive earlier for lunch or stay later for dinner.

Favorite Things in Montalcino

• Go for a stroll down into Piazza del Popolo and onto Via Giuseppe Mazzini, which is where most of the local shops, antique stores, and other boutiques are
• Get a glass of wine on the terrace at the historic Caffè Fiaschetteria Italiana 1888 Srl
• Take a walk down to “Montalcino panoramico” for lovely views back to the town
• See historic sites in the village like Fortezza di Montalcino, Cathedral of the Holy Savior, and Palazzo dei Priori
• Get a bite to eat at Re di Macchia, Enoteca Grotta del Brunello, and Osteria di Porta al Cassero (Don’t forget to try the local ice cream at Gelateria del Corso Artigianale di Santoro Maria)

Montepulciano

Probably the most famous hilltop village in this part of Tuscany, Montepulciano is everything Renaissance architecture and wine. I visited a second time on this trip, and my consensus is this: the town really leans all things wine. There are a few historic sights to see, the old town to walk in, and then tons of wine-related activities.

If you’re looking to experience Renaissance architecture and wine, this is where to visit. The Vino Nobile di Montepulciano is its signature red wine. It’s elegant, structured, and one of Tuscany’s most prestigious DOCG wines. In the town of Montepulciano, you’ll find many places to try the wine.

The main “attraction” in Montepulciano is the Historic Underground Cellars (Cantine Storiche). Many wineries have labyrinth-like cellars beneath the town, some dating to the Etruscans, where you can taste Vino Nobile right at the source.

Favorite Things in Montepulciano

• Stop by a Cantine Storiche to try wine, like Cantina Contucci, De’ Ricci, and Talosa, all within the old town
• Visit the Sanctuary of the Madonna di San Biagio, on a cypress-lined path on the other side of the village
• Stroll through the citadel, visiting churches like Cattedrale di Santa Maria Assunta and Chiesa e Convento di San Francesco

Bagno Vignoni

Also known as Tuscany’s “spa town,” Bagno Vignoni is one of those gems that often gets overlooked. It’s reason enough to bring your swimsuit if you’re interested in dipping into ancient thermal waters. The town itself is quite small, with a handful of trattorias and shops that line the original thermal spa.

If you’d like to go swim in the free spas, all you have to do is follow the Parco dei Mulini path. It takes you out to the natural thermal pool in less than a 10-minute walk from the city center.

Favorite Things in Bagno Vignoni

• Soak in the baths of Parco dei Mulini
• Get a bite to eat somewhere in the town center (I’d recommend Osteria del Leone)

Monticchiello

Quite possibly the smallest village in Tuscany, blink and you might just drive through it! Enclosed by medieval walls and crowned with a slender stone tower, the village of Monticchiello looks out over a rolling patchwork of cypress-lined roads and golden fields. This village is small, but it is truly postcard-perfect. I’d come here for a stroll to enjoy a quieter, smaller village, and then consider having lunch at one of the trattorias in town.

Favorite Things in Monticchiello

• Go for a picturesque village stroll
• See the famous cypress-lined tree road from “Punto Panoramico Cipressi Monticchiello“
• Have a meal at Ristorante Daria or Ristorante Bronzino

San Quirico d’Orcia

Often referred to as the most local of the villages in the Val d’Orcia, San Quirico is a small, good for a few hours and a meal kind of place. It’s a single main street that cuts through the historic old town, and is lined with restaurants and a handful of shops.

Another big draw here is visiting the Rose Gardens and Horti Leonini, a beautifully manicured garden just off the old town. I’d say an hour or two here is plenty to see the village!

Favorite Things in San Quirico d’Orcia 

• See Horti Leonini and the old town
• Have a meal at the famous Ristorante Trattoria Osenna

---

Standout Restaurants to Try in the Val d’Orcia

In addition to the restaurants mentioned above in the villages, there are about a half-dozen restaurants I’d go out of my way for. Some are in the countryside or at hotels, and a few in the villages.

Lupaia Restaurant

One of the most standout dining experiences was at our hotel, Lupaia. Their onsite restaurant, while open for all meals, really shines as a cozy, elevated trattoria come nighttime. The menu is fixed, three-course, and changes daily. It is open to outside guests; you just need to call in advance for a reservation. The food here is truly fantastic. I would also consider coming in just for lunch, as the setting is stunning.

Sette Di Vino in Pienza

Our favorite meal of the trip that felt authentically local in terms of a village restaurant was Sette Di Vino in Pienza. It’s rustic, tableside fare that just felt like I was eating in a family’s kitchen. Their Tuscan bean soup, artichoke, grilled cheese, and charcuterie were absolutely fantastic.

Podere Il Casale

When it comes to agriturismo dining in Tuscany, I feel like there are dozens to choose from. I had heard good things about Podere, and it didn’t disappoint. The setting is sublime, set at the point of the hill looking back to Pienza. The food was fresh, ingredients from their farm, and served with warm hospitality. I really enjoyed it here, very family-friendly yet still felt elevated.

Dopolavoro La Foce

One of those restaurants everyone seems to talk about is Dopolavoro, and I can tell you, I agree. It’s set off the road, kind of a destination in itself, and the restaurant is airy and cozy. The food here feels elevated yet down-to-earth and is best known for its aged meats. We tried a handful of dishes from their beef tartar (best of the trip) to their grilled meats, and it was fantastic.

Osteria Acquacheta

Osteria Acquacheta is one of Montepulciano’s most beloved and most characterful places to eat. It’s famously rustic, lively, and unapologetically devoted to traditional Tuscan cooking. The star of the show is the bistecca alla fiorentina, cut dramatically to order right in front of you and cooked over their wood fire. It’s a tough reservation to get, but if you can, try to book ahead.

Buon Gusto Gelateria

Shoutout to Buon Gusto, who fed us gelato in multiple towns from Pienza to Montepulciano, and we absolutely adored this gelato shop and their flavors.

---

The Foods to Try When in Val d’Orcia, Tuscany

So much of the magic of Val d’Orcia is found at the table, in simple dishes that showcase what this valley does best. From pecorino and pici to hearty soups and bright, tomato-forward salads, these are the flavors I seek out every time I’m back in this corner of Tuscany.

• Pecorino: sharp, salty sheep’s cheese
• Salame di cinghiale: rich, wild boar salami
• Pici pasta: thick, hand-rolled noodles
• Cinta Senese Salumi: a wild pig, salami
• Ribollita: hearty, vegetable bread soup
• Panzanella: fresh, tomato bread salad
• Olive Oils: lovely, regional options!

---

Things to Do in the Val d’Orcia, Italy

What I love most about the Val d’Orcia is how much there is to do simply by being out in the landscape. I love wandering quiet roads, stopping at small chapels, soaking in hot springs, and exploring the villages at an easy pace. These are the experiences that make this part of Tuscany so special. Read my Tuscany itinerary for a more detailed plan for visiting the highlights below!

See Cappella della Madonna di Vitaleta (Chapel Vitaleta)

Tuscany is dotted with small chapels and historic cathedrals, but one of the most famous is Cappella della Madonna di Vitaleta. The chapel is believed to date back to the 16th century. It is linked to a revered statue of the Madonna that, according to local tradition, was brought to Vitaleta by the Renaissance sculptor Andrea della Robbia. The version you see today was rebuilt in the 19th century in a neoclassical style, giving it its clean lines and elegant symmetry.

There are a few ways to see this historic chapel. For photographers, one of the best views of it, if you have a high-powered zoom lens, is to park at the top of the road where Agriturismo Poderino is. You get a bird’s-eye view of it.

If you want to get close to the chapel and go inside, then there is a designated parking lot for it. From there, you have to walk about 10 minutes down a dirt road that is well-marked and clear to the chapel itself. It’s very popular at sunset, so plan ahead. At the chapel itself, there is also a well-rated restaurant called Vitaleta Gourmet, open seasonally.

Go for a Countryside Walk Near Pienza and to Panorama il Gladiatore Cosi Bella

Some of the best things to do in Tuscany are to just go for a walk. There are several country roads to go for a walk, but one of the best is the road underneath the village of Pienza, Panorama il Gladiatore Cosi Bella. We actually stayed at an Airbnb there for a few days and walked these roads a few times.

The road to walk is where Corsignano Church is, and you can either follow Strada di Terrapille out to the gladiator road, or continue onto a dirt road in the countryside. Enjoy the fresh air here, it is really some of the best views in Tuscany for a walk.

Another popular area for walking is the Lucciola Bella Nature Reserve. It’s a protected natural area in Tuscany, really lovely for the clay hills and typical landscapes. There are a few walking trails here as well.

Photograph the Famous Cypress Trees

If you’re into photography or simply enjoy stunning landscapes, the Val d’Orcia is one of the most famous areas for it. It’s most known for several cypress tree roads and clusters that are quintessential Tuscany. The first famous one is Cipressi di San Quirico d’Orcia, arguably the most famous and most-photographed cypress grove in Val d’Orcia (if not all of Tuscany). There are two groupings: a “lower” grove visible from the road, and a “higher” circle of cypresses accessible via a dirt track on foot.

Another famous one to photograph is Poggio Covili Cypress Avenue, a beautiful avenue of aligned cypress trees, with the entrance along the main road (SR2 / Via Cassia) south-east of Bagno Vignoni. The other main one is Monticchiello Cypress Road (a winding cypress-lined road), a curvy, “snake-like” road lined with cypresses just outside of the village of Monticchiello.

Shop Homemade Pastas at Mulino Val d’Orcia

Mulino Val d’Orcia is a lovely stop if you’re looking to pick up house-made pastas and sauces. The historic mill has been making organic pasta since the 90’s. It’s a small store, but inside you have dozens of dried pasta choices, all made with their organic flour. You can also buy their flour in bulk.

Try Your Hand at Making Pasta

I’ve done several pasta-making classes all over Italy, and this is so fun to do when visiting, as each region has its specialty. I did a pasta-making class the last time I was in Tuscany at our hotel, and enjoyed the time to slow down and make a meal. I found this pasta-making class at Agriturismo Podere Spedalone (close to Pienza), where you’ll get to make your own pasta and classic Cantucci cookies. This pasta-making class in Montepulciano was another I had saved.

Soak in the Hot Springs of Bagno Vignoni

Tuscany is home to several hot springs. If you’re looking to go for a soak, especially in the colder months, head to Bagno Vignoni. The central square is itself a giant thermal pool fed by volcanic springs, but where you soak is just about a 10-minute walk past it. The Old Thermal Mills Park (Parco dei Mulini) is the main, free, open area to go. Otherwise, if you want something more elevated for a spa day, I’d book a day pass at the Terme Hotel Adler Spa Resort.

Travel Tip: Further south is the famous Bagni San Filippo Hot Springs. It’s only about a 30-minute drive south of the valley, and it’s worth the time to experience the limestone pools hidden in the forest.

Taste the Wines of the Region

This area is absolutely packed with wineries; you’ll feel like it is almost entirely vineyards. The two DOCG wines that are the most popular are Brunello di Montalcino DOCG and Vino Nobile di Montepulciano DOCG. There are a few ways to go about tasting wine in Val d’Orcia. The first would be to stop into a tavern or wine bar and order wine. The other would be to go to a winery or two.

Most of the wineries do require reservations in the valley, so keep this in mind. If you’re looking to not have to self-drive and have a day set up for you, my recommendation is to book a tour like this 3 Montepulciano estate visit. A few wineries I keep tabs on, if you’re looking to set up an individual tasting, are:

• Fabbrica Pienza
• Bindella (touch further east)
• LIGNANELLO
• Sasso di Sole

Book a Truffle Hunting Class

If you have the chance to be in Tuscany during truffle season, don’t miss the opportunity to go on a truffle hunt. Some of the best truffles in Europe come from Tuscany, and in the late summer into fall, the truffle season begins. It’s done traditionally with a truffle dog, so most tours will head out for an hour or two to find truffles, and most include some kind of tasting or lunch. Most of the hunts are further north near San Gimignano, but this tour here is one of the few in Montepulciano that includes the hunt and lunch.

---

Save This Post for Later on Pinterest