A Tour of Tuscany: Siena and Val d’Orcia

Discover the real Tuscany route you've seen in the movies from your own car.

Siena, San Gimignano and the Val d'Orcia will not disappoint you.

When you type "Tuscany" in google-images, you discover green meadows, with soft curves. Like turtle shells, overlapping one after the other until you lose sight of the horizon, dotted by tall, dark cypress trees, pointing to a blue sky dotted with small passing clouds. Sometimes these cypress trees mark out azigzag path; sometimes the meadow is covered with poppies, or has turned a yellow-tan color after the summer heat. In the background, or in the background, a farmhouse can be seen.

They are images that spread peace, inner well-being. And from here, you may start dreaming of traveling to Tuscany. This is what happened to me.

But beware, Tuscany is very large, it is full of charming villages with medieval air and beautiful landscapes, although not all exactly like the ones you have seen in those photos, it will depend on the area you go to.

If, like me, you fell in love with these photos and want to see these places with your own eyes, you should go to Val D'Orcia, in the province of Siena.

You can take ideas from the following 3-day drive we took in April 2015.

Siena

Siena has always been considered Florence's rival, and I have to say that, in my opinion, the contest is very even. If you want to know more about Florence, don't miss the entry Walking around Florence.

The center of Siena is a very well preserved medieval city, not in vain is considered a World Heritage Site by Unesco.

Small and easy to walk around, it is located as an inn on a hill. In one day you will be able to walk it without problems and see its most important places of interest, such as the following:

Piazza dil Campo

It is a curious fan-shaped inclined square in the center of Siena.

The Palio di Siena, a famous horse race that pits the two districts of Siena against each other, is held here twice a year (on July 2 and August 16).

In the lower part of the square is the 'Palazzo Comunale', which houses a museum and the ' Torre di Mangia'. Mangia Towerwhich offers spectacular views of the city and the surrounding hills. Entrance to the tower cost 10€/adult in 2015.

Duomo

It is included in the Metropolitan Opera of Siena. Of Gothic construction, it has a beautiful white, green and red marble façade.

Its interior is richer than that of the Duomo of Florence, and it houses on one side the Piccolomini Bookshopwhich is said to be worth seeing.

We were unable to enter because Holy Thursday mass was taking place, but we will return.

The Metropolitan Opera of Siena also houses the Opera Museum, a baptistery and the crypt.

Where to stay

We spent one night at the B&B Le Chiarine.

It offers a good quality/price ratio, has spacious and clean rooms with comfortable beds. Breakfast is simple but plentiful.

It is located in a quiet residential area, somewhat removed from the medieval center, with an easy access of 10-15 minutes on foot.

A great bonus of this accommodation are the views of the Duomo overlooking the city that can be seen near the B&B, on the way to the center. We would not have enjoyed them if we had not spent the night there, and I assure you they are worth it.

In addition, around B&B Le Chiarine it is easy to find free parking (something quite scarce in Italy).

However, pay attention to the signs that indicate, at the beginning of the streets, which day the cleaning will take place, since one or the other side of the street must remain empty for the cleaning team to pass at the indicated time.

Val d'Orcia

Here is a description of the route we followed in Val d'Orcia, a photographic route through one of the most bucolic places in Tuscany.

Remember, especially on this route, you should enjoy the road.

San Quirico d'Orcia

This was our first stop after leaving Siena. A small medieval walled village on top of a hill.

Cobblestone streets with flowers in the windows, the small church 'Collegiata dei Santi Quirico e Giuditta', the gardens 'Horti Leonini', will make your visit a pleasant walk .

La Foce

If you look at the route map at the bottom of the page, you can see the route we followed to go from San Quirico d'Orcia to La Foce. I invite you to follow the same route.

In it you will find all those photos you want to take on this trip.

You will be able to stop at viewpoints or widenings of the ditch and spend minutes, or hours, printing on your retina cypress roads that, zigzagging, culminating in a farmhouse on a green hill.

Wherever you look, you will be amazed.

La Foce is not a village per se, it is an old estate, with beautiful gardens and various types of rental accommodation in a privileged setting, all of which are quite expensive.

We did not go inside, but I advise you to go around the wall to its lowest part. From there you can admire one of the most photographed zigzags of cypress trees, which you have already seen from the road. Although this time you will admire it from the front, without telephone lines or trees that get in the way of the panoramic view.

Simply overwhelming.

Monticchiello

Monticchiello is a delightful medieval village, again perched on top of a hill.

Enjoy the views of Tuscany, with Pienza in the background, stroll through its cobblestone streets and, if you can, have lunch, dinner or a coffee with sweets on the terrace of the restaurant La Porta' restaurant.

The location alone would be enough to recommend it, but the food and wine are also very good. Of course, call ahead and make a reservation, or you won't find a table.

Pienza

It is another medieval walled village slightly larger than Monticchielo, on top of a hill, with intricate alleys and beautiful views of the Tuscan valley.

We stayed here at the 'Piccolo Hotel La Valle', a very clean and correct 3 star hotel, which offered free parking and a simple breakfast included in the price. Being just outside the wall, it was very quiet at night.

Montepulciano

Montepulciano is a medieval walled village with a steep slope on top of a hill, the most touristic of all those we visited in the Val d'Orcia.

It is famous for its wines, not in vain is dotted with wineries that offer tastings of their products to tourists.

At the architectural level, in my opinion, its greatest distinctive feature with respect to other medieval villages in the area is the colossal Sanctuary of the Madonna of San Biagioa temple located at the foot of the hill on which Montepulciano rests.

As you approach it from Pienza, you will be able to appreciate this wonderful picture, which will delight photography lovers.

San Gimignano

Our last stop was San Gimignano, north of Siena, in the Val d'Elsa.

This small walled town is dotted with towers (although there were many more, only 15 remain standing), making it look like a medieval New York. Wealthy families showed their power by building towers higher than those of others, hence the curious profile of this town.

San Gimignano is very well known internationally, or what is the same, very touristic. This fame is understood when you see it with your own eyes, and will imply that you walk through its streets and squares accompanied by hundreds of people, which will make it lose quite a bit of charm.

We were very lucky, since it rained cats and dogs the day we visited.

It is true that we were running with a battered umbrella from one side to the other so as not to get too wet, and the sky was gray, which made the photos much worse.

But the streets were almost deserted, everyone had taken refuge in bars, restaurants, hotels...

Suddenly, that village was really medieval, stone gray, soaked by a torrential rain that never stopped, lonely... It seemed that we had traveled back in time. 

We spent the night at the 'Agriturismo Sulle Orme Di Dante'.with free parking a short walk from the village.

I recommend walking, the parking outside the wall is quite expensive and runs out soon (as long as it is not pouring, as it happened to us).

This agriturismo has a delightful decor, with period furnishings, both in the rooms and in the bathrooms, all very well kept and clean. It also has a swimming pool in the garden overlooking San Gimignano.

Breakfast is good, but it is not included in the price, you will have to pay for it separately.

In San Gimignano I can recommend the 'Pizzeria Ristorante Il Trovatore', outside the walls. Delicious pizzas and meat a la fiorentina. Remember to book in advance by phone if you want a table here.

If you have any doubts or questions, or need any more details that I haven't mentioned, feel free to leave a comment below. I will be happy to help you.

Useful Links

• B&B Le Chiarine.
• Other hotels in Siena and surroundings.
• La Porta, Monticchiello.
• Piccolo Hotel La Valle, Pienza.
• Agriturismo Sulle Orme Di Dante, San Gimignano.
• Flights to Italy:Trabber,eDreams,Momondo, andVueling.
• 5% discount on IATI insurance.

Oh, and if you're touring Italy, don't miss these blog posts:

• Venice in the off-season.
• Weekend in Rome.
• A stroll through Florence.
• The Abbey of San Galgano in Tuscany.
• Route along Lake Como.
• The natural park of Maremma and its unspoiled beaches.
• Bologna, the city of arcades.
• Route through Umbria, the secret neighbor of Tuscany.
• The wonders of the Amalfi Coast.

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