Is Pienza the most romantic town in Tuscany? Well, it has streets called ‘kissing’ and ‘love’, some of Romeo and Juliet was filmed here and it is considered a perfect example of Renaissance architecture. That makes it a very romantic and beautiful place to visit. But other than that, this hill top town is a paradise for food lovers especially if cheese is your passion and it’s surrounded by some of the most stunning views of Tuscany, with hills of Val d’Orcia, an area that has inspired poets, writers and artists for hundreds of years.
The town is a UNESCO World Heritage Site and the entire Val d’Orcia is on the list of UNESCO’s World Cultural Landscapes. That’s quite an accolade!
This town was once an insignificant hamlet, that was intended to be a city, but it ended up being barely bigger than a village!
It was in 1459 that Pope Pius II began a scheme to redesign the ancient hamlet, the place of his birth, into a model Renaissance city with palaces, churches, piazzas and ordered streets. It was renamed Pienza to mean the city of Pius.
It turned out, however, that he died 2 years after the work began. Therefore, only a little of the plan was completed. The result is a beautiful and proud little town surrounded by stunning natural beauty of the Val d’Orcia countryside.
We entered through the main gates, Porta al Prato, straight towards the main street.
(If you turn immediately right here, you can get some of the most incredible views over the Tuscan countryside. More about views later).
The main street
The beauty of this historic street is one reason Pienza is the most romantic town in Tuscany.
The main street is pretty with so many quality artisan shops, cafés and restaurants it is impossible not to stop and ponder each one.
The town has hardly changed since the 15th century and perfectly preserved iron work hint at it’s historical past life.
It is cool despite the high temperatures, shaded by the tall stone buildings either side of the narrow street.
The shops are almost entirely high quality and artisan in nature. They are a delight to wonder round. Much smaller than in Montepulciano, but full of well made tasteful products.
We found that the prices were pretty high, but probably worth it.
Some of the products seemed a little flamboyant!
Local foods shops
The Tuscan’s are extremely proud of their local produce.
They are very attractive and the goods are packaged in a way that suggests quality and small handmade batches. This is a heavenly place for foodies.
You’ll find olive oil, cured meats, fine wines, pici (handmade) pasta and spices.
The Pecorino of Pienza
Pienza is considered the “capital” of pecorino cheese, because it produces a very high quality cheese made from an especially flavoursome and aromatic milk from the sheep that live in the pastures of Val d’Orcia.
There is a cheese festival every first Sunday in September. Pienza holds an ancient and folkloristic game called the Palio del Cacio Fuso. The players of each town district have to roll an entire round of pecorino cheese around the fuso, a wooden spindle located at the centre of the square.
This tasty cheese is renowned worldwide and delicious and can go from a delicate flavour to a decisive one based on how aged it is.
We sampled some at the Avignonesi Wine Tour And Lunch and it was really wonderful.
Samples are readily available all over the town. Does the local cheese help make Pienza the most romantic town in Tuscany? Maybe not, but there again, food and love are connected in a deep level, don’t you think?
Tuscany is famous around the world for it’s beautiful landscapes, but the south of Siena is, to my eyes, the best of all. Pienza is fairly near to the Medieval Hill Town Of Montepulcianio another stunning town well worth visiting.
Within the landscape ancient olive trees rest neatly in patches, vineyards are surrounding honey stoned villas and hills are topped with medieval towns crowned by cypress trees. We stayed in an incredible villa surrounded by the owners vineyard Villa Montepulciano, Tuscany.
One viewing spot that we missed is turn right immediately at the gate. You’ll face a slopping path. This apparently leads to a spot where you can see miles of gorgeous countryside.
Our first viewing spot from Pienza can be found by turning right at the Central square, Piazza Pio II, from the main street.
You will pass a beautiful Well, known as ‘the well of dogs’. The view will appear through a narrow gap by another plainer Well.
It’s a quieter spot for a group photo than some of the other spaces, but as you can see (below) couple shots work best!
Another place to try is from the Palazzo Piccolomini to the right of the Duomo. It has a fantastic Loggia with a pretty hanging garden. From here you can enjoy the breathtaking panoramas of the Val d’Orcia Valley.
Palazzo Piccolomini was even used for filming some scenes of the romantic movie Romeo and Juliet, where the first encounter took place between the two lovers at the Capulets’ home.
Our favourite view, however, is from the walled path at the very edge of the town. Turn right off the main street (past the square) and you’ll come across it.
It’s a dreamy spot.
Now, how’s this for a romantic stroll? These stunning views are partly what makes this the most romantic town in Tuscany.
The town gives a superb example of Renaissance, according to humanist urban reorganisation. Therefore, there is a central square where pretty much all the important monuments are located.
The dream of Pope Pius II was to create a Utopian city, exemplifying the principles and philosophy of classical times and of the great Italian Renaissance.
The square is filled with important palaces so Pope Pius made sure a tower was added to the Cathedral to stand above all the other buildings, as a sign of faith.
The town hall is ‘younger’ building on the piazza, with its ample loggia and façade decorated with a scratched plaster technique. It also has a brick bell tower, however, it is shorter than the cathedral’s to symbolise the superior power of the Church.
Pienza is the only Renaissance town centre in Italy to have survived the centuries perfectly intact.
The square rebuilt by Rossellino in the 15th century, is flanked by the cathedral and three harmonious palaces: one for the government (the town hall above), one for the bishop and one for Pope Pius II. It is known as an ‘ideal city of the Renaissance’. All though, of course is is not a city.
In the square look out for holes that pocket the walls of one of the palaces dating from a siege in the 1550s and a mortar bombardment in the Second World War.
The back streets are peaceful, neat and although it is the main streets that are crammed with cafés, homely trattorias and artisans’ workshops, you will still find things to look at.
Like beautiful lace hanging at the windows, flowers and washing lines, things that make these houses into homes.
It’s really nice to see where the (very lucky) locals live.
The most romantic town in Tuscany is on the Love Route!
It’s no surprise that Pienza is part of Tuscany’s Love Route.
Pienza is a romantic city because of its streets with “lovely” names such as Via dell’Amore (love street) and Via del Bacio (kiss street). If you are in a romantic mood you should definitely come here for a smooch!
It was only this morning that these two love birds got engaged..!
So, we were all in a ‘lovely’ mood! It definitely feels like the most romantic town in Tuscany to us!
It wasn’t difficult to find these streets, both are just off the main street.
Pretty restaurants pepper the town, you’ll walk past many handsome eateries. What makes more sense when visiting the most romantic town in Tuscany than sharing a meal with the one you love?
Very attractive ‘osterie’ serve local foods. Often you’ll find pecorino cheese prepared in countless original ways.
We enjoyed an ice cream and coffee from Buon Gusto Gelateria. They had tables under umbrellas and provided a much needed rest bite.
Check out Sette di Vino, Osteria La Porta, Agriturismo Ristorante La Fonte and L’Osteria Baccus.
There are also a couple of cafés in the town. This one is pretty decent. Good to pop in for a coffee at least.
We absolutely loved this most romantic town in Tuscany. It was a divine place to visit with your loved one or ones, in my case. Make sure you put it on your list of things to do in Tuscany.
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