The essence of Tuscany from Pienza to Florence

Last modified 19.03.2022 | Published 08.08.20172015's, Italy, Southern Europe, Travelogue

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What is the essence of Tuscany? See if you can find an answer in this article from a road trip in the region. It starts in Cortona, stops at Pienza, runs through the Val d’Orcia, passes Siena and San Gimignano and ends up in Firenze (Florence).


This is the third article from a road trip in central Italy. This was going to be a long day and highly exaggerated in terms of ambitions, even if my belly had been working with me. The road trip on Day 4 is marked with a violet colour on the map below. Apart from Cortona these places are all UNESCO World Heritage Sites, and that it what we were hunting on this road trip of central Italy.




Its name is derived from Pope Pius II who in the 15th century ordered a new town to be built on the hill overlooking the Val d’Orcia, by transforming the old town of Corsignano, the pope’s very own birthplace. The result, with the piazzas and palazzi and general layout, is in turn considered to be the birthplace of Renaissance urban planning. It was built as an ideal city and has survived to this day largely unchanged. For this reason it is a World Heritage Site.



The best thing to do is finding a place to park at either end of the rectangular shaped historical city. Arriving here in August is not the best time of year, so we found a large car park outside the middle section. That is not a big obstacle because the centre is surprisingly small. The main street runs the length of the city and is called Corso il Rossellino. It is only 350 metres long. The distance across the historical centre is merely 150 metres. The Medieval or rather Renaissance centre has almost no motorised traffic and one should be aware that many car parks around it is reserved for residents.


What to see and eat

The main interest to visitors lies in crisscrossing the streets of Pienza on foot. Sooner or later you will end up at the central piazza, called the Piazza Pio II. This square is surrounded by the city hall, the cathedral and two palaces – the Borgia (Vescovile) and the Piccolomini. We dropped the Borgia but bought a ticket for an audio-guided visit to the Palazzo Piccolomini. This family of Pope Pius II became the dominant family of Pienza even in the centuries after the Pope had passed away. It is well worth a visit, not least for its “hanging” garden on the back providing a spectacular view of the countryside.

I have no thorough experience of wining and dining in Pienza. We had lunch at a recommended restaurant called Trattoria La Buca delle Fate. Try the mixed platter for your entry and you will get a taste of (among other things) the local cheese. It is called Pecorino di Pienza and is made from sheep’s milk. You will smell it as you walk the streets of Pienza.

Our visit was at daytime, but I would not hesitate spending an evening or night here – for instance in a romantic hotel. The atmosphere must be wonderful – at least if you’re interested in this kind of city life.

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Val d’Orcia

The valley Val d’Orcia south and west of Pienza is also a World Heritage Site. The gently rolling hills of this beautiful landscape was during the Renaissance redesigned, or sculptured, following ideas of good governance and good appearance. Painters of the Sienese School arrived to depict it and the people living off the land. On my map you will find markers of four towns in the valley: Radicofani, San Quirico, Castiglione and Montalcino. They are all acknowledged as being beautiful, and in combination they offer a rough indication of the area that is included in the heritage site.

We did not visit these four towns. Instead we followed the advice given in a guidebook we had brought with us. We took road SP71 north from Pienza towards Castelmuzio and turned west in the direction of Cosona, then road SP137 before hitting the main road at Torrenieri. This route is partly on gravel road on a ridge providing exceptional views in all directions. Follow my map, and you will not be disappointed.

I’m Norwegian and used to a green and very fertile countryside all through the summer months. This part of Italy is in August rather dull in terms of colours. The harvesting is over, apart from occasional fields of drying sunflowers. What was left was rolling hills, stone buildings, winding and dusty roads, and here and there the iconic evergreen view of Tuscany – a row of tall and strong cypress trees. In the images below you will find examples of how it looked like in reality – and examples of what extensive use of filters can produce.

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Siena and San Gimagnono

Next on our list was Siena. This extremely popular tourist destination was high on my partner’s bucket list. Unfortunately it came up too late in the day to stop at. In addition I had this terrible belly producing nothing but anxiety. Pressing on north on the motorway we also passed a sign showing the road to San Gimignano. These two historical cities are both World Heritage Sites and I had fortunately been to both before.

San Gimignano’s towers are the main attractions although the entire city centre is a definite highlight to anyone’s visit to Tuscany. The towers were built as a sort of manifestation to the wealth of the builders. Many towns had them, but the number of remaining tower in this town outweighs the rest.

Siena is much larger, and was at its height competing with Florence in terms of wealth and power. The main sights revolve around the central piazza called the Piazza del Campo, with the city hall as a natural centre. In addition the cathedral is a must-see in Siena. Twice during the summer, the Palio provides splendid occasions to observe medieval competitions, colours and atmosphere. 

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Instead of stopping here, we went straight to Florence for a couple of days. The story from this spectacular city will be presented in the next and last chapter from this road trip.


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Was this the essence of Tuscany? Perhaps, at least hints of it. The following map shows the places and attractions on this road trip, or rather these road trips. We had several days on the road. The best impression of the map is when you expand it into a new tab, and then zoom in and out as you like. Click the markers to get more information and links to further reading.


I have been to Italy on several occasions. See all articles from Italy, including travelogues and videos. See all pictures from this particular trip.

The road trip in 2017 is described in the following articles.