Siena and the Hill Towns

Once Florence’s most fearsome rival, Siena remains the perfect medieval city to the south, rich with Gothic palaces and magnificent art.

Proud of its past, Siena celebrates the Palio, with energy and emotion uncharged over the centuries. Siena is the perfect introduction to the celebrated hill towns, with the towers of San Gimignano and the Etruscan shadows of Volterra close at hand.

Piazza del Campo Siena
Piazza del Campo Siena

Italy’s most enchanting medieval city, Siena is the one trip you should make in Tuscany if you make no other. Once there, you will undoubtedly be drawn to Italy’s most famous hill town, San Gimignano, known as the “medieval Manhattan” because of the enormous towers, built by rival families, which still stand today.

Like Siena, it benefitted from the commerce and trade along the pilgrimage routes, as the wonderful art in churches and museums attests to. Equally intriguing is a visit to Volterra, an Etruscan town famous for its alabaster.

Southern Tuscany is perhaps less familiar than the Chianti region to the north, but prestigious wines are made south of Siena, too, and the scenery is a classically Tuscan as anywhere. On your way down, don’t miss a stop at the Abbazzia di Monte Oliveto Maggiore, sublimely decorated with Renaissance frescoes.

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Pleasures and Pastimes


If you already been eating in Tuscany, chances are you’ll recognize much of what’s on the menu in these towns.

Some local specialities include pici (fat spaghetti almost as thick as a pencil); zuppa alla volterrana (a local version of ribollita, a soup with bread and vegetables); the white wine of San Gimignano (called San Gimignano and sold in every enoteche, or wine bar); and sweets in Siena such as panforte (traditional Sienese Christmas fruitcake with honey, hazelnuts, almonds, and spices).


Siena, San Gimignano, and Volterra are among the most visited towns in Tuscany, so there is no lack of choice for hotels across the price range.

The best accommodations, however, are often a few kilometres outside town. Every year there seems to be more old villas and monasteries converted into charming, first-rate hotels, as well as simpler agriturismo (agritourist) farmhouses, usually available on a weekly basis.

The location makes a car necessary, but the splendor of the surroundings usually outweighs any problems getting in and out of town.

When to Tour Siena and the Hill Towns

The region enjoys particularly sparkling weather in spring and fall. In summer, the same sun that makes the grapes grow can turn the packed streets unpleasantly hot–it is always easier to work with the local schedule than against it: If you get an early start, you can enjoy the sites in the cooler morning hours, and return to have an afternoon siesta while the sun is the highest.

Make a point of catching the passeggiata (evening stroll), when the local descend to the main street. Siena fills to the brim in the weeks surrounding the running of the Palio on July 2nd and August 16th, when prices, crowds, and commotion are at their highest.

Palio di Siena
Palio di Siena

In the winter months, you will probably have towns mostly to yourself, although the choices for hotels and restaurants can be a bit more limited than when the season is in full swing.


The she-wolf and suckling twins on the city’s emblem show Siena’s claim to share common ancestry with Rome; the town’s legendary founder, Senius, was a son of Remus, the twin brother of Rome’s founder Romulus.

Archaeological evidence suggests that there were prehistoric as well as Etruscan settlements here first, which undoubtedly made way for Saena Julia, the Roman town established by Augustus in the early 1st century.

Siena rose to prominence as an essential stop on that most important of medieval roads, the Via Francigena (or Via Romea), prospering from the yearly flow of thousands of Christian pilgrims coming south to Rome from Northern Europe. Siena developed a banking system (the first bank, Monte dei Paschi, is still very much in business) and dominated the wool trade, thereby establishing itself as a rival to Florence.

The two towns became regional powers and bitter enemies, each town taking a different side in the struggle that divided the penisula between Guelph (loyal to the Pope) and Ghibellines (loyal to the Holy Roman Emperor).

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Victory over Florence in 1260 marked the beginning of Siena’s Golden Age. Even though the Florentines avenged the loss nine years later, Siena continued to prosper. Over the following decades, Siena erected its greatest buildings, including the Duomo and Palazzo Pubblico; established a model city government based on the Council of Nine; and became a great center of art, with painters at the forefront of the Renaissance. All of these achievements came together in the decoration of the Sala della Pace in Palazzo Pubblico.

That Siena was for centuries the great rival (in art, in trade, in textiles in banking) to Florence, leaves us only to wonder what greatness the city might have gone to achieve had its fortunes been different. But the Plague of 1348 decimated the population, brought an end to the Council of Nine, and left Siena economically weak and vulnerable to outside domination.

After four centuries of conflict, Siena succumbed to Florentine rule in the mid-16th century, when a year-long siege virtually eliminated the native population. Ironically, it was precisely this decline (along with the steadfast pride of the Sienese) prevented further development, to which we owe the city’s marvellous condition.

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With its redbrick streets and steep alleyways, stunning Gothic Duomo, bounty of early Renaissance art, and glorious Palazzo Pubblico overlooking its magnificent Campo, Siena is often described as Italy’s best-preserved medieval city. But while much looks as it id in the early 14th century, Siena is no museum. Walkthrough the streets and you can witness a charming anachronism: The medieval contrade, the 17 neighborhoods into which the city has been historically divide, are vibrant and very much alive.

Look up from just about any street and you will know the contrada– Tartuca (turtle), Oca (Goose), Istrice (porcupine), Torre (tower)—you are walking in, as its symbol will likely be emblazoned on a banner or engraved in the street. Ask any Sienese and there will be no doubt—local identity is still very much defined by the contrada into which you were born ad raised, baptized, and married, and loyalty and rivalry run deep.

Mappa Contrade Siena
Siena Contrade

At no time is this more visible than during the centuries-old Palio, a yearly horse race through the main square, but you need not visit during the wild festival to come to know the rich culture and enchanting pleasures of Siena.

Contrade Senesi

Exploring Siena

If you come by car, you’ll be better off leaving it in one of the parking lots around the perimeter of the town, as access is restricted or just plain difficult in much of Siena. practically unchanged since medieval times, Siena is laid out in a “Y” over the slopes of several hills, dividing the city into terzi (thirds). Although you will find the most interesting sites in a fairly compact area around the Campo at the center of town, be sure to leave some time to wander into the narrow streets that rise and fall steeply from the main thoroughfares.

If your feet have had enough, there are usually cabs at the bottom of the Campo, and orange electric minibuses ply their way through the crowds and between the major sites.

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A Good Walk

Try to avoid passing through Siena in less than a day, missing the opportunity to really explore the town, which is more than the sum of its most notable sites.

Begin with a coffee on the Piazza del Campo, the focal point of the city, and considered by many to be the finest public square in Italy. Visit the Palazzo Pubblico, with its Museo Civico and adjacent tower, the Torre del Mangia.

Torre del Mangia Siena
Torre del Mangia Siena

Cross the Piazza and exit via the stairs to the left of the Fonte Gia to Via di Città. Just to the left is the 15th-century Loggia della Mercanzia, where merchants and money traders once did business. Commerce is still pretty active along ahead on Via di Città is the enchanting Palazzo Chigi-Saracini, where concerts are often held.

Step in to admire the especially well-preserved courtyard. Continue up the hill on Via di Città and take the next street on the right, Via del Capitano, which leads to Piazza del Duomo. The Duomo is a must-see, along with the frescoes inside in the Libreria Piccolomini. Off the side is the Museo dell’Opera del Duomo and the Battistero (around the other side of the Duomo), and across from the Duomo is the Ospedale di Santa Maria della Scala and its Museo Archeologico.

Chief among Siena’s other gems in the Pinacoteca Nazionale, several blocks straight back down Via del Capitano (which becomes Via San Pietro). The church of San Domenico lies in other direction (you could take Via della Galluzza to Via della Sapienza) and nearby is the Casa di Santa Caterina, where one of Italy’s patron saints was born.

Sight to See

Baptistery of San Giovanni (Battistero di San Giovanni)

The Baptistry of St John is located near the Duomo in the center of Siena. Built-in the same Tuscan Gothic style, although less externally ornamented – the facade is unfinished. But it’s inside that is really worth seeing.

The baptismal font is hexagonal, decorated with panels depicting scenes from the life of John the Baptist, by leading artists of the 15th century: Donatello, Ghiberti, Giovanni di Turino and Jacopo della Quercia. Six sculptures represent Faith, Hope, Fortitude, Justice, Charity and Providence. There are bronze angels by Donatello and prophets by della Quercia. And completing the intense decorative motif, the walls and ceiling are frescoed.

Siena Cathedral (Duomo)

Siena’s magnificent Tuscan Gothic cathedral is not to be missed. And if you’re in Siena you can’t miss it because it dominates the place. Rising high with its magnificent white and greenish-black stripes, it has a bit of red thrown in on the front facade and lots of detailing – including scrolls, biblical scenes and gargoyles. In the centre is the huge rose window designed by Duccio di Buoninsegna in 1288. Statues of prophets and philosophers by Giovanni Pisano which used to adorn the facade are now housed indoors at the nearby Museo Dell’Opera.

Inside the place is equally impressive with art by Donatello, Bernini and early Michelangelo. Some of the best pieces such as Duccio di Buoninsegni’s Maesta have been moved next door to the Museo Dell’Opera. Unlike other cathedrals where you are craning your neck to see magnificent ceilings and frescoes, here you need to look down at the mosaic floor. The whole floor is tiled and is one of the most impressive in Italy.

Siena Civic Museum (Museo Civico di Siena)

The Palazzo Pubblico is hard to miss. A magnificent stone and red brick building has begun in 1297, with excellent towers and crenellations, it is everything one could hope for from a Gothic town hall. Situated on the lower side of the Piazza Campo, the building is shaped to fit the design of the civic square and has a subtle curve to it.

These days it retains its government functions and also houses the city museum, Museo Civico, which is well worth a visit for its frescoes, paintings and sculptures. The Sienese school was artistically significant and the late medieval frescoes were some of the first to depict non-religious themes. Instead they made statements about government, justice and patriotic devotion. The most significant is the huge fresco cycle of 1337 by Ambrogio Lorenzetti, entitled Allegory of Good and Bad Government; it’s not difficult to get the painting’s message.

Basilica of San Domenico (Basilica di San Domenico)

Saint Catherine of Siena brought this basilica to prominence by taking her vows here in 1363 when she was just 15. Having had her first vision at the age of 6 near this church and deciding to follow a religious life from 7, she went on to lead a highly significant existence tending the sick, receiving the stigmata from a wooden cross in Pisa, mediating for the Papacy during its exile in France and also the time of Great Schism of the West when the cardinals could not agree on who should be the next pope.

She died at the age of 33 in Rome. In 1461 she was made a saint, in 1866 she became a patron saint of Rome, and in 1939 a patron saint of Italy. Finally in 1999, she was proclaimed a co-patron saint of Europe.

Mangia Tower (Torre del Mangia)

Rising high above the Piazza del Campo is the bell tower, Torre del Mangia, built in the early 1300s. It reaches nearly 90 metres above the Palazzo Pubblico and was intended to be exactly the same height at the bell tower of the Duomo to indicate equality between church and state. These are the two structures that still soar high above the historic center of Siena.

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If you have the stomach for heights and no fear of tight spaces, climb the 500 steps for a great view down onto the square and across the city beyond. The irony is, of course, that the tower is named after its first watchman, an overweight glutton, hence the name Tower of the Eater. It’s not sure he would ever have made it up the top to see the view.

Piccolomini Library (Libreria Piccolomini)

The Piccolomini Library is a library within the cathedral in Siena, Italy. The library was designed in the 1400s, and visitors can admire the beautiful ceiling that is covered in frescoes painted by Pinturicchio in 1502. The colorful frescoes depict images of figures in luxurious clothing, indoor settings, and detailed landscapes. The walls show important stages of the life of Pope Pius II in ten different sections. Some of the parts of his life that you can see painted here include when he was an ambassador to the European courts, paying homage to the new Emperor and then to the Pope at the time, presenting Eleonora of Aragon to the Emperor Frederick III, becoming a cardinal, and then becoming the Pope.

The library was built by Pope Pius III to house the manuscripts of Enea Silvio Piccolomini, his uncle who was Pope Pius II before him. Though most of the manuscripts are not here, visitors can see several hand-designed volumes on display.

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Santa Maria della Scala

Santa Maria della Scala was one of Europe’s first hospitals. Established by the Catholic priests of the Siena Duomo, it housed and cared for those making the pilgrimage across Europe to Rome, and also took care of the local poor and took in orphaned and abandoned children.

To impress God and each other, the local wealthy families of the 15th century gave generously to the hospital, including commissioning important artists to decorate the building. The external frescoes are now all lost but interior works remain, including a series of frescoes telling the story of the hospital located in the Pilgrim’s Hall on the fourth floor.

Nearby is the original church that the hospital grew around, Church of Santissima Annunziata. On the third floor is the original of Jacopo della Quercia’s Fonte Gaia, the fountain of joy – a copy is in the Piazza del Campo.

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Arriving and Departing

By Bus

Several buses a day run from between Rome and Siena (2:30 hrs). There is frequent service between Florence and Siena (1 hr), Volterra (2 hrs), and San Gimignano (1 hr).

By Car

The area is easily reached by car on the A1 Motorway (Autostrada del Sole), which runs between Rome and Florence (exit on S326 for Siena). From Florence, the fastest way to Siena and the hill towns is via the toll road through Poggibonsi. Alternatively, the Strada Chiantigiana (S222) is the scenic route through Tuscany’s famous wine country.

Welcome to Chianti Wine Region of Tuscany

By Plane

The airports nearest to the region are Pisa’s Aeroporto Galileo Galilei (Phone:050500707), Florence’s Peretola (Phone:055333498), and Rome’s Fiumicino (Phone:0665953640).

By Train

Frequent trains make the 80-minute trip between Florence and Siena. The train station is out of the old city, but cabs are readily available. Train service runs between Siena and Chiusi-Chianciano Terme (where you can make Rome-Florence connections), making many stops (Montepulciano, Sinalunga, and Asciano included). In many cases, bus trips are quicker. All stop in Poggibonsi; from there, buses go on to San Gimignano and Volterra. For state railway (FS) information, call 147/888088) toll-free.

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