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Cypress avenues, medieval towns on hills and an endless expanse – the Val d’Orcia corresponds pretty much exactly to those images of Tuscany that you always have in your head. So if you want to head for the typical Tuscan photo spots: You’ll find what you’re looking for in Val d’Orcia!

Perhaps you’re considering spending your holiday in Val d’Orcia ‘Orcia to spend? In our article we tell you everything you need to know about it. We show you the most beautiful towns and places in Val d’Orcia. Of course, as always, there are our very personal insider tips for the perfect trip. Here we go!

1. The Val d’Orcia in Tuscany: Things worth knowing & first travel tips Where is the Val d’Orcia and how do I get there? The Val d’Orcia is in the south of the province of Siena, about an hour’s drive from the provincial capital of the same name, Siena. The valley is named after the river Orcia.

The Val d’Orcia is relatively extensive and extends over a total of five municipalities (as well as countless smaller villages). For this reason alone we strongly recommend that you arrive by car, in order to be as flexible as possible on site.

You have two options: Either you lay back the entire route from Germany or Austria in your own car. (Whereas the 000 Hours drive from Vienna almost scream for a stopover.)

The slightly more time-saving alternative: You fly and take a Rental car. Florence is the main airport. From there it takes about two hours by car to Val d’Orcia. Our tip: You can find cheap flights on Skyscanner. We always book our rental car through Sunny Cars.

What can I expect in Val d’Orcia? Tuscany postcard motifs: Cypress avenue meets picturesque agriturismo. And behind it: a gently rolling, picturesque, spacious landscape. Some of Tuscany’s most famous photo spots are in Val d’Orcia. In any case, look forward to Tuscany par excellence. It’s not for nothing that the Val d’Orcia is a UNESCO World Heritage Site. Medieval town: Whether Montalcino, Pienza or Montepulciano – in Val d’Orcia you will find some picturesque medieval towns. (We deliberately choose “small towns” because they are almost small villages.) They are usually enthroned on a hill and exude a very magical flair. Viticulture: The Val d’Orcia is home to one of most famous and exclusive red wine varieties in Italy, the Brunello di Montalcino. So if you would like to do a wine tasting (our tip follows!) or enjoy a glass or two, the Val d’Orcia is the right place for you. When is the best time to travel to the Val d’Orcia? The Val d’Orcia has changed Appears relatively strong over the seasons. In spring, for example, the landscape is quite lush green. Here you can look forward to the poppies in May and June, which conjure up a sea of ​​red dots.

In summer the landscape gradually changes and becomes golden yellow thanks to the wheat fields. Then it is definitely the hottest time of the year – and of course also the one when Tuscany is literally overrun by people in some parts. Personally, we would rather skip the summer.

The autumn is really pleasant in terms of climate and it’s slowly becoming a little quieter again. However, the landscape then appears (especially when it hasn’t rained much and not least because of the harvested fields) quite dry and barren.

We ourselves were out and about in October (in a period with very little rain) in the Val d’Orcia. So you can get an idea of ​​what we mean by “dry” from our photos. Next time we would definitely come in spring. Above all, the time when the poppies blossom must be fantastic in the Orcia Valley.

How much time should I allow for a holiday in Val d’Orcia? Of course there are several options here. Variant 1: You choose the Val d’Orcia as your home base for your vacation in Tuscany and make excursions from there (e.g. to Siena or Florence). Then we would advise you to spend about a week in Val d’Orcia.

In general, you should know that the Val d’Orcia is located more in the south of Tuscany and some famous travel destinations (eg Lucca or Pisa) are a fair bit away.

Therefore, many (including us on our second trip to Tuscany) decide to make a road trip with several stops. In this case, we recommend planning two to three nights for the Val d’Orcia.

2. Towns worth seeing in Val d’Orcia In this chapter we introduce you to some of the most beautiful towns in the Orcia Valley. In general, you should know: The cityscape is usually very similar. (Of course, you don’t have to go through all the cities, you can of course concentrate on one or two.)

You can expect a in all places. Medieval historic town center with enchanting alleys. Because all the cities mentioned are on a hill, you can always enjoy beautiful views of the Val d’Orcia.

Montepulciano Montepulciano is majestically enthroned on a round 146 meter high hill and is beautiful to look at from afar. But wait until you take a closer look at this gem!

With about 14.000 Residents is Montepulciano the largest city in the Val d’Orcia. Compared to the other places, everything is a bit more spacious here – nevertheless you can easily walk through the historic center in less than an hour.

Recommendations & Sights in Montepulciano It’s best to start your tour of discovery in the heart of the city, at Piazza Grande, so to speak the main square of Montepulciano. Two buildings in particular draw everyone’s attention: the gigantic Santa Maria Assunta Cathedral and the town hall, known as the Palazzo Comunale.

Our little insider tip: Make sure you climb the steps of the town hall tower. From up here you really enjoy a fantastic view in all directions. Definitely one of our highlights in Montepulciano.

In the north of the Piazza Grande there is another well-known attraction: the Grape and Lion Fountain. Afterwards, we would recommend that you take a leisurely stroll through the old town and let the medieval alleys work their magic on you.

For a stop, we can highly recommend the legendary Caffè Poliziano. The atmosphere in this Art Nouveau café is really quite special. The seats on the terrace with a view towards Val d’Orcia are very popular. We enjoyed the espresso macchiato together with a delicious brioche at the bar in the appropriate style.

Pienza You should only visit one village then we would recommend Pienza. Pienza is considered one of the most beautiful towns in the Val d’Orcia – and rightly so, in our opinion. The town is pleasantly tranquil and you can look forward to a fantastically beautiful flair.

Sights & Highlights in Pienza Pienza is really mini – believe us: You will find it easy to find your way around. Our little exploration tour starts at the main square of Pienza, the Piazza Pio II, which is well worth seeing.

The most important sights of Pienza can be found on the main square. On the one hand there is the imposing Cathedral of Santa Maria Assunta with its white Renaissance facade. In addition, of course (how could it be otherwise) is the town hall (Palazzo Comunale) with the striking tower.

A special feature of Pienza is its Panorama path, which runs along the city walls in the south of the old town. From here you can enjoy a really nice view down into the Val d’Orcia. If you want, you can also have a drink here – for example in the very great Bar Idyllium.

Afterwards, we definitely recommend a walk through the picturesque alleys in the east of Pienza. We really liked it here. If you feel like having a gelato, drop by Gelateria Buon Gusto.

Our tip: Before or after visiting Pienza we recommend a stop at Podere Il Casale. We had a lovely meal here in a fantastic rural setting. You can find more information in the chapter with our culinary tips for the Val d’Orcia further down in this blog article.

Montalcino Last but not least, you get to pretty Montalcino in the west of the Val d’Orcia. Anyone who travels to Montalcino usually has one thing in mind: to try the exclusive red wine Brunello di Montalcino, which is considered one of the best red wines in Italy and whose vines grow around Montalcino.

But a stopover in pretty Montalcino is definitely worthwhile for all those who are not particularly interested in wine. We really liked it here – especially because there are great photo spots and places to discover off the beaten track.

Sights & our tips You could start your tour of discovery with a panoramic view over Montalcino: you can enjoy a wonderful view from the fortress in the south of the old town. Access is in the small wine shop in the courtyard of the fortress. (Attention: Only cash payment possible.)

Then you enter the narrow streets of the old town of Montalcino. One of the most famous squares in Montalcino is the picturesque Piazza del Popolo. The square is not as spacious as one might expect from a main square, but it is very picturesque.

The narrow square catches the eye immediately ale Palazzo dei Priore, the government building of the city, whose tower rises up. Also very pretty is the opposite Renaissance loggia from the 14. Century. Our tip: The loggia is home to the highly recommended Alle Logge di Piazza restaurant.

Don’t miss the short walk up to the Cathedral of Montalcino (Concattedrale del Santissimo Salvatore). You don’t really have a distant view here, but the cathedral is definitely worth seeing.

A little insider tip is the picturesque Palazzo Pieri. In the courtyard of this one historic building is now a bar. Very great location! Opposite the Palazzo Pieri is the city museum of Montalcino, the Museo Civico e Diocesano, where historical art treasures can be admired. We didn’t visit it but found the courtyard with the concept store and the adjoining cafe very charming.

3. Photo spots in the Val d’Orcia along the panoramic roads Some of the most famous photo spots in Tuscany are located in the Val d’Orcia. The landscape has not just been photographed since Instagram – the Val d’Orcia was already popular in the Renaissance immortalized on canvas.

Many of these views are located along the Panorama Road SP146, which crosses the Val d’Orcia from west to east. In principle, all you have to do is drive this route and keep your eyes open.

Don’t be surprised: some of these photo spots are well known and no longer insider tips. This means that you often have to share the space on site (even in the off-season) with other photographers and their tripods. (Not that it means we didn’t warn you.)

Podere Belvedere One of the most iconic photo motifs of Tuscany is this stone house near San Quirico d’Orcia called Podere Belvedere. It is surrounded by cypresses and perched on a small hill in the characteristic landscape of the Orcia Valley.

One of the main reasons why the place is so popular is its ease of access: Just a few meters from the panoramic road SP146 away, enjoy already the best view of this little gem.

We recommend you to come at sunrise. In October, the sun rose almost perfectly on the horizon, so we were able to take great backlit shots. The magical lighting mood in the early morning was unique.

Cappella della Madonna di Vitaleta If you get to the panoramic road SP146 from Podere Belvedere If you continue towards Pienza, within a few minutes you will see a tiny chapel on the right in the distance, the Cappella della Madonna di Vitaleta.

There is a small viewpoint on the side of the road. However, we ourselves drove closer to the chapel. The access road is signposted and is a few hundred meters further in the direction of Pienza on the right-hand side.

Park your car about 5 minutes’ walk from the chapel removed. Quite apart from the fact that you can also enjoy a great view of the Val d’Orcia from here, we found the motif with the chapel and the curved avenue of cypresses much more exciting from this perspective than from the main street .

Agriturismo Baccoleno Attention – Instagram hotspot! Well, luckily we didn’t experience it that bad in October, but this photo motif is definitely one of the most well-known in Tuscany.

It’s a bit off the classic route , approximately 35 minutes north of Pienza along the road SP60. To be precise, you are no longer in the Val d’Orcia, but in the adjacent Crete Senesi region.

The curved one , lined with cypresses belongs to the Agriturismo Baccoleno – a beautifully renovated country house where you can stay overnight. If you (like most) only come to take pictures, you have to park on the side of the road. (Please be careful not to block the access road.)

Avenue of cypresses Poggio Covili Another avenue of cypresses, which also belonging to an accommodation is that of Agriturismo Poggio Covili. This can only be used if you are staying overnight. Nevertheless, this almost perfectly straight avenue is also great to look at from the outside.

Our conclusion: None of the really big highlights in Val d’Orcia, but if you’re nearby, it’s worth a short photo stop. You can park your car directly in front of the access road.

Cypress ring near San Quirico d’Orcia We don’t often think it takes a drone to get the best view – but it definitely applies here. The cypress ring only looks from a bird’s eye view really special.

It is located in the middle of fields about 5 minutes drive west of the town of San Quirico d’Orcia. To be more precise, there are actually two photo motifs in the immediate vicinity: On the one hand, the already mentioned and in our opinion much more interesting cypress circle, and on the other hand the cypress grove, i.e. a collection of several trees that are close together.

There are two possibilities to drive there. 1. (Our recommendation): You park, quite uncharmingly, in the small parking bay on the main road SR2. From there you can already see the cypress grove. You can also walk up the hill to the cypress ring.

The second option is what Google Maps suggests: it gets even closer to the Cypress Circle via bumpy dirt roads. Verdict: Takes a lot longer and gives you a dust-covered car. So we wouldn’t recommend it.

Genna Borborini Maria Eva (Gladiator House) This iconic stone house, made famous by the movie Gladiator. What you don’t see in the photo: the view and the path are blocked by a huge lattice gate. (Of course, this is a private property.)

In this respect, the charming photo does not reflect the reality that says: You park on the side of the road on the main street to capture the motif . Nevertheless, a short stopover is of course worthwhile here, since this house is directly on the panoramic road SP146 lies.

4. Food & Drink: Special Cafes & Restaurants Podere Il Casale (near Pienza) Tuscany feeling as you wish! If you want to dine in Val d’Orcia, in the middle of nature, with a wonderful view and at the same time fantastic, then we can only warmly recommend the restaurant of Podere Il Casale.

More precisely, this is organic farming, producing cheese and olive oil, for example. The attached restaurant serves delicious Mediterranean dishes. We were here at lunchtime and thanks to the good weather we were able to sit outside on the terrace – a dream!

The menu has many meat dishes, but also there are a few options for vegetarians. The menu changes regularly and offers lots of seasonal items. In any case, it tasted excellent to us and the bread that was served was also delicious.

The access to the restaurant is via a gravel road, which fortunately is not too bumpy. In return, once you arrive, a dreamlike tranquility awaits you in the heart of Tuscany. We strongly recommend that you make a reservation because the restaurant is incredibly popular with holidaymakers.

Taverna del Grappolo Blu (Montalcino) This very popular restaurant is located in the heart of the old town of Montalcino. It doesn’t have Michelin stars, but it has been awarded for being great value for money. And we can only agree with that.

The ambience is rustic and traditional. The menu features countless Italian classics, some of which are also vegetarian, such as delicious pici (a special Tuscan pasta). We were overwhelmed with the sheer endless selection of wines. If you want to try the famous Brunello di Montalcino, this is the place for you.

Our conclusion: Very good value for money Relationship. We strongly recommend a reservation, as the restaurant is often fully booked.

Caffè Poliziano (Montepulciano) If you feel like coffee and cake in Montepulciano, you should definitely stop by this historic coffee house. The Art Nouveau ambience may seem a bit outdated, but very authentic.

If you want, you can (like us) take a seat in style at the counter. The advantage (apart from the flair): You get the espresso cheaper, like everywhere in Italy. Alternatively, the seats on the small terrace with a view down into the Val d’Orcia are very popular.

The cake display case is well stocked and offers every Tuscan specialty you can imagine. We chose the chocolate filled brioche which was excellent.

Caffè Poliziano also has its own restaurant area with a large terrace. However, we did not eat there, so we cannot judge the quality of the dishes.

5. Our tip: Wine tasting in Val d’Orcia Unwritten rule: One should not leave the Val d’Orcia without trying at least once the region’s most famous red wine, the Brunello di Montalcino. The vines of this exclusive top wine grow around the town of Montalcino.

The Brunello di Montalcino has its price – and with good reason. It is not sold until a good five years after the harvest. It has to mature in oak barrels for at least two years and in the bottle for six months. Incidentally, the cheaper sister of the Brunello is the Rosso di Montalcino.

You can of course taste the Brunello di Montalcino in almost every restaurant in the region. However, we would recommend a wine tasting . We chose the highly recommended Canalicchio di Sopra winery because we stayed in the associated accommodation. (Also highly recommended – more information can be found in the next chapter.)

For 25 Euro per person you can at a Participate in a guided tour of the wine cellar and then taste three red wines. Very exciting and also very entertaining for us, who are not typical wine connoisseurs.

6. Hotel tip for the Val d’Orcia Arrived – and immediately in love! Therefore we would like to recommend our fantastic accommodation in Val d’Orcia, the Borgo Canalicchio Di Sopra Relais. You stay here at the foot of the town of Montalcino, surrounded by vines and olive trees.

The accommodation belongs to the winery of the same name, which is known for the production of the famous Brunello di Montalcino. You can expect a beautiful, wonderfully well-kept complex with just five apartments or suites. (Some of them have space for up to six people.) The rooms are quite classic and very comfortably furnished.

Family and personal – that’s how the ambience can be described. You are received incredibly hospitably – we have rarely experienced that. The service is excellent. For example, there are great recommendations for nearby restaurants that were easily booked for us. Simply great!

It’s a pity that the bathing season was already over when we visited. Otherwise you can make yourself wonderfully comfortable by the pool with a view of the olive grove. The breakfast was definitely one of the best of our Tuscany trip. Countless regional delicacies of very high quality are on offer.

Our conclusion: If you are looking for a very special, well-run accommodation in the Val d’Orcia, you have come to the right place. We would have loved to have stayed longer and would not hesitate to stay here again.

Here you can book the hotel: Borgo Canalicchio Di Sopra Relais

7. Map: All places & photo spots at a glance Finally, we have drawn all the highlights in Val d’Orcia on this map so that you can hopefully navigate from A to B on site. A little tip: Simply click on the rectangle at the top right to open the map easily in the Google Maps app on your smartphone.

Transparency: Affiliate Links This blog article contains our personal recommendations in the form of so-called affiliate links. If you book or buy something through the links, we will receive a small commission. For you, this does not change the price at all. A thousand thanks from both of us!

Have you ever heard of Val d’Orcia in Tuscany or maybe even spent your vacation there? We look forward to hearing about your experiences and additional tips in the comments.