23 Magical Things to Do in Siena, Italy (2023)

Siena is one of the most magical, enchantingly medieval cities in existence.  Italians call it the museum city, as it feels like you’ve entered a living museum when you enter the city’s walls and stroll its narrow streets past ornate stone mansions, historic churches, and spectacular squares, like the incomparable Piazza del Campo.

The place is so special that the entire historic center was named a UNESCO World Heritage Site in 1995.  I have visited Siena several times on day trips from the Florence area — most recently in 2023 — but the city has its own riches that will repay an overnight stay or more, to soak in the environment when the tour buses have left and the image of medieval times seems even more alive.  

It is one of my favorite places to visit in Tuscany, and even though there are a wealth of museums and churches with impressive artistic collections, this is a city that one can revel in simply walking the streets, viewing historic buildings at every turn, eating at a charming osteria or restaurant and learning about the past times when Siena grew rich from its wool industry, was rich culturally, architecturally and was one of the most powerful banking centers in Italy.  

Siena is situated on a series of hills in the Tuscan countryside south of Florence.  The two cities were chief rivals in the 13th and 14th centuries, and before it ultimately fell to the Medici. The colors of Siena’s stone buildings have given rise to the burnt-red color, sienna, and the warm colors come alive in the morning hours and especially the evening sun.  Stand in the atmospheric Piazza del Campo and watch as the sun’s rays light up the tower (Torre del Mangia) of the Palazzo Pubblico and creep across the sloping surfaces of the shell-shaped square, encircled by handsome places and home to the twice-yearly Palio, one of the world’s most famous horse races.  

Its Duomo or cathedral is one of the most spectacular in Italy, rising atop one of the city’s hills and a beautiful presence with its striped marble and ornate façade.  Its interior riches and associated buildings like its Baptistery and Cathedral Museum could take you half a day alone to explore.  The climb to the top of the Duomo or the Torre del Mangia in the Piazza del Campo give ravishing views over this stunning city, its architecture and surrounding countryside.

What else is special about Siena?  Art lovers will love exploring the collection of Sienese art in the city’s Pinacoteca, while even the former hospital near the Duomo is an art treasure filled with frescoed walls, and even the city’s archeological museum within its holdings.  

The city has historically been divided into seventeen contradas or local districts, with their fanatic devotion from residents.  Each has its own name and mascot such as the Turtle, Goose and Porcupine, local church and even museum.  And this devotion is played out most noticeably during the running of the Palio in July and August.  

Siena’s population was decimated by both the Black Plague in 1348 and a year-long siege by Florence in the mid 16th century.  With little population and resources to grow, the city remained in its medieval condition that we enjoy today as this time capsule of ancient times at least in its outward appearance.  

Admire Siena’s Architectural Masterpiece: the Piazza del Campo

The stunning centerpiece of the city is the Piazza del Campo, one of the most dramatic squares in all of Italy.  Its shape is unique in that it is like a red-bricked shell, divided into nine sections to represent the old Government of the Nine who ruled Siena from 1292 to 1355.  The area slopes down to the foot of the square, where the magnificent Town Hall and Mangia Tower provide striking medieval civic architecture.  

The square is rimmed by lovely palazzos housing restaurants and shops on the ground floors, and the head of the square contains the Gaia Fountain, the largest in the city, and built in 1419 by master sculptor Jacopo della Quercia.

This is a place you’ll want to relax in and take in the passing scene and your beautiful surroundings, perhaps while taking a meal or a drink at one of the many outdoor tables at the restaurants lining the square.  The city’s medieval streets radiate out from the Campo, and twice a year during the summer, it is transformed into the site of the most popular festival in town, the horse race called the Palio.   

Palazzo Pubblico (Siena’s Town Hall)

The elegant Palazzo Pubblico at the base of the Piazza housed the city’s government offices.  Built in the 1300s, it has a ground floor of white marble topped by floors of red brick construction with decorative windows topped by the city’s black and white coat of arms.  Today it houses the Civic Museum, one of the most important sites to see in Siena.

The founding myth claims the city was founded by sons of the founder of Rome, one of whom, Senio, gave his name to the city.  They arrived on two horses, one white and one black, and the coat of arms reflects these two colors.  The Torre del Mangia rises dramatically alongside the Palazzo and there is also a small outdoor chapel that was built in 1352 to give thanks for the end of the Black Death plague of 1348 that had ravaged the city.  

Torre del Mangia

The striking red brick Torre del Mangia arises from the side of the Palazzo Pubblico and is the most dramatic feature of the Campo’s skyline, rising 285 feet high and topped with a white marble bell tower.  The first guardian of the tower, called ‘il mangiaguadagni‘ or he who eats his earnings, allegedly squandered his pay on meals at the city taverns, giving rise to the Tower’s name Torre del Mangia.

Built between 1325 and 1348, the Tower’s height exactly matches that of the Cathedral to symbolize the equality of church and state in Siena.  The Tower can be climbed for magnificent views over the city.  

The admission fee is 10 euro for the Tower, or 15 euro if combined with the Civic Museum next door in the Palazzo Pubblico.

Fonte Gaia (The Fountain of Joy)

The Fonte Gaia captured the enthusiasm the community felt when water finally reached the Piazza del Campo after 8 years of work through an aqueduct and underground tunnel system.  It is now one of the centerpieces of the Piazza, sitting atop the head of the square across from the Palazzo Pubblico.

The original fountain was constructed in 1343 and replaced in 1419 by the famous version by Jacopo della Quercia which contained statues of the Madonna and Child, angels, figures representing the Cardinal Virtues and Justice, and side panels with representations of the Adam and Eve’s expulsion of the Garden of Eden.  The square marble fountain’s sculpture was replaced by copies in 1858, and the originals are on display in the Santa Maria della Scala Museum on Piazza del Duomo.  

Ready for the horses! Photo credit: Petr Jilek/Shutterstock

Palio of Siena

Twice a year, on the 2nd of July and on the 16th of August, the famous festival of the Palio takes center stage in the Piazza del Campo, as it has for hundreds of years.  Sand carpets the square in preparation for the horse race, which pits ten of the 17 contradas who have won the chance to compete in the current year.  They are battling for the honor of winning the prize, a silk banner that can be proudly displayed by the citizens of the winning contrada. Throngs of people fill in the central part of the square and others watch from the balconies of the palazzos ring the Campo.  Adding to the festive atmosphere are flag throwing demonstrations by citizens in medieval garb and parades with costumed bands.

It’s a no-holds barred bareback race, where riders must circumnavigate the outer part of the square three times.  The winner is determined by the horse that finishes first, even if that horse has lost its rider!  I watched the Palio one year on tv in Italy with my wife’s Italian father, and the winning horse lost its rider halfway through the contest.  How odd to see the champion horse being cheered as it circled the square alone! 

If you can’t experience the Palio in person, or want to avoid its crowds, you can take a three-hour walking tour that explains the history of the event while taking you to one of the historical contradas, then visiting the Duomo and finally trying some of Siena’s typical sweets, all at a cost of $244.11 per person.  

Visit Siena’s Most Spectacular Churches

Siena’s Cathedral (Il Duomo)

Siena’s Duomo is one of Italy’s most spectacular churches and is one of the city’s absolute can’t miss sights.  Initial construction was completed in 1264, but the upper layer was added in the 14th century and the exterior mosaics as late as 1877.  The Duomo itself is filled with artistic treasures, and its beauty will take your breath away.  

There is more to the Duomo complex than just the cathedral, which once was intended to be much larger, but the ravages of the Black Death in the 14th century (and the discovery that the foundations couldn’t handle the extra weight) meant that only the walls of the intended structure were built, which now house the Cathedral Works Museum and provide one of the most stunning views of the city from its rooftop walkways.  The Baptistery sits just behind the Duomo down a flight of stairs from the main piazza.  

Start your visit with the façade of the Duomo, which has intricately detailed sculptures by Giovanni Pisano, beautiful entry doors and Venetian mosaics at the top.  The striped marble on the façade and bell tower are eye catching.  Once inside, you’ll hardly know where to look first.  The floors are covered by 59 beautiful marble mosaic panels completed by around 40 Sienese artists between 1372 and 1547.  Most of the panels were completed by Domenico Beccafumi.  The panels are normally only uncovered in their entirety from August to October each year.  

The line of striped marble columns leads your eye down the nave to the altar, large ornate rose window and then up to the blue ceiling decorated with gold stars and lined by busts of popes and Roman emperors.  

The marble pulpit is one of the glories of the cathedral, built by Nicola Pisano and featuring fabulous carvings with a base resting on carved lions.  The biblical stories captured brilliantly in marble include the Nativity, the Flight into Egypt, the Crucifixion, and the Last Judgement.  

Sculptural work in the Duomo is done by such famous figures as Donatello, Michelangelo, and Bernini.  Also be sure to look for the entrance to The Piccolomini Library, which features a magnificent set of 10 frescoes created in 1502-08 by Pinturrichio commemorating the major life events of Pope Pius II, who was a member of the Piccolomini family, with a charming statue of the Three Garces in the middle.  Other places to seek out are the Chigi Chapel with sculpture by Bernini, and the Chapel of St John with a bronze sculpture of St John the Baptist by Donatello.  Michelangelo contributed a statue of St. Paul that many art historians believe is a self-portrait with his broken nose.

Around the side of the cathedral is the entrance to the Crypt, which houses not mausoleums but a set of bright 13th century frescoes of New Testament scenes that were discovered when the previously enclosed space was excavated only in 1999.

With so much to see, a guided tour can help you understand everything better.  This three-hour city tour includes a guided visit of the Duomo for $106.73 per person.


The Baptistry sits just behind the Duomo and was built to shore up the apse area of the cathedral.  It has an unfinished façade, but inside you’ll find its chief artistic glory, the marble baptismal font created from 1417-1430 by Jacopo della Quercia.  Its famed bronze panels depict key moments from the life of St. John the Baptist and were done by della Quercia along with Donatello and Lorenzo Ghiberti (famed for the bronze Gates of Paradise from Florence’s Baptistry).  One of the most acclaimed panels is the Feast of Herod by Donatello from 1427.  In addition, there are ceiling frescoes throughout the building painted by the artist known as Vecchietta.  

Basilica of San Domenico

This austere looking brick, Gothic style Basilica of San Domenico dates from the early 13th century but is intriguing mainly for its association with St. Catherine of Siena, who was declared a patron saint of Italy in 1939.  

In the St. Catherine chapel is displayed the saint’s head and finger, displayed on a marble altar from 1469.  As macabre as this may sound, the veneration of such items was important to the faithful in medieval times, and the famous Via Francigena holy route from Canterbury and northern Europe to Rome passed directly through Siena, bringing many pilgrims. The Chapel also features two works from 1526 depicting scenes from Catherine’s life by the artist known as Il Sodoma.  The Chapel of the Vaults contains a painting by Andrea Vanni from around 1400 that is considered a true portrait of the saint.  

From the apse-side terrace, there are excellent views of the Duomo and rooftops of Siena. Admission is free.

Oratory of San Bernardino 

The Oratory of San Bernardino is from the 15th century and built where the Franciscan friar St. Bernardino of Siena preached.  Located adjacent to the Basilica of San Francesco, it is about a 10-minute walk from the Duomo.  Today there are two levels of beautifully frescoed walls and ceilings, plus a small Diocesan Museum of art of Sienese church paintings from the 13th to the 19th centuries.  The highlight is the upstairs chapel, covered in 16th century frescoes by the likes of Beccafumi and Il Sodoma, showing scenes from the life of the Virgin and saints.  

Admission to the Oratory is included on the Opa Si pass that covers admission to the Duomo and its related museums.  The cost of the basic pass is 15 euro.  There is not a separate admission for the Oratory and given that it is a bit on the outskirts of the center, it pays to call ahead to make site it is open.  

Learn about the past in Siena’s Best Museums

Civic Museum

The Civic Museum of the Palazzo Pubblico is the must-see counterpoint to the religious marvels of the Duomo.  Here in the rooms where the Government of Siena met, there are masterpieces of secular art that commemorate the rulers of the Sienese republic.  

Highlights include the Sala del Mappamundo or World Map Room with its large wooden disc by Ambrogio Lorenzetti depicting the Republic’s territory.  In addition, you’ll find the exquisite Maesta or Majesty by Simone Martini from the early 1300s, portraying the Madonna surrounded by saints and angels looking over the proceedings, and providing divine protection over the city.  On the opposite wall is a notable equestrian portrait of Guidoriccio da Fogliano, riding past one of his castle conquests as a mercenary for the Siena republic.  

The admission fee is 10 euro.

The stained glass window in the Duomo’s museum. Photo credit: Travelvolo/Shutterstock

Cathedral Works Museum (Museo del Opera del Duomo)

Housed in the section of the so-called New Duomo where the extension of the cathedral was to have been built, the Museo del Opera del Duomo or Cathedral Works Museum is the repository for art treasures that were moved from the cathedral for protection.  These include the original statures by Giovanni Pisano from the façade, along with the city’s most precious work of art, Duccio’s 1311 Maesta showing the Virgin and child surrounded by adoring saints.  In addition, there are relief works by Nicola Pisano, sculptor of the pulpit inside the cathedral, and the stained-glass windows made for the apse in the 1280s.  

Here is also the entrance to the so-called Facciatone which takes you up through the walls of the unfinished section of the cathedral to the rooftops, where there are walkways providing amazing views over the city.  

Admission is included as part of the Opa si pass for the Duomo and its circle of attractions for 15 euro for the basic version.  

Pinacoteca Nazionale

The collection of the Pinacoteca Nazionale is the single best assemblage of Sienese paintings.  It provides a thorough history of the key artists and paintings across the 12th though 16th centuries.  Since 1932 the gallery has been housed in the elegant Palazzo Buonsignori.  

Here you will find works by Duccio, a student of Cimabue, as well as Ambrogio Lorenzetti and the preparatory sketches by Domenico Beccafumi for his 35 marble panels for the Duomo’s floor.  What is noticeable here is that Sienese artists maintained their adherence to Byzantine gold and Eastern styling in their work as Florentine artists were adopting new techniques during the Renaissance.  

Religious imagery continued to dominate the subject matter for the Sienese works, and the newer advances in painting such as perspective and use of emotions in human subjects was not adopted as it was in Florence.  

The admission price for the gallery is € 8.00 for adults.

Santa Maria della Scala

Santa Maria della Scala was once one of Europe’s oldest civic hospitals, caring for the sick and infirm as well as abandoned children from the 12th to the 18th centuries.  It also cared for the needs of passing pilgrims, situated as it was along the Via Francigena pilgrimage route that passed directly through the city.  The hospital commissioned frescoes and altarpieces from the income it generated through its landholdings over the centuries.

No longer a hospital, the large complex has been turned into a museum complex, with a series of spectacular 15th century frescoes by Vecchietta and others in the Pilgrims Hall that capture the activities of the hospital and its doctors and nurses in caring for patients.  The complex sits in the Piazza del Duomo, directly across from the cathedral’s front.  

Allocate several hours at least to explore the four floors of exhibits in this large museum complex.  Other highlights to look for include the atmospheric National Archaeological Museum set in the basement and the original 1419 sculptures from Jacopo della Quercia’s Fonte Gaia.

The admission fee is 9 euro for separate entrance, but there are combined tickets with the Duomo and its related museums.

Sanctuary of St. Catherine

The Sanctuary of Saint Catherine is a house museum dedicated to Saint Catherine of Siena, one of Italy’s patron saints.  The Home-Sanctuary gives visitors a good perspective on Catherine’s life and times.  She was born here in 1347, spending her childhood here with 23 siblings.  

Saint Catherine battled corruption in the church and was successful in convincing the pope to leave Avignon and return the papal seat to Rome. She was devout from an early age and entered a Dominican order of nuns who looked after the poor and sick of Siena.  Even so, she was able to spend much of her life continuing to live in the house of her birth.  

In this peaceful setting you will see what remains of her birthplace, plus several chapels including one that has a 12th century crucifix from Pisa from which beams of light were supposed to have given Saint Catherine the marks of Christ’s stigmata.  There are colorful frescoes from Saint Catherine’s life in the chapels.  In the former kitchen there is a striking ceramic floor, and there is also a peaceful cloister area with a marble well.  

The admission is free.

Take in the Best Viewpoints

Torre del Mangia

The Torre del Mangia overlooks the Piazza del Campo.  It was built in the mid-14th century and stands at 289 feet tall, matching exactly the height of the Duomo.  For wonderful views overlooking the city, climb the 400 steps up the tower.  The entry cost for the Tower is 10 euro.  

The Facciatone del Duomo

The Facciatone is the walkway on the top of what would have been the façade of the New Duomo.  It is the city’s second most popular viewpoint behind only the Torre del Mangia.  The Facciatone views provide close-up looks from on high of the entire Duomo complex and over the rooftops to the Torre del Mangia in the Piazza del Campo.  

Entrance is included in the basic Opa Si pass for the Duomo and its related attractions, at a price of 15 euro per adult.

Explore the City’s Unique Food and Wine

Siena and its surrounding countryside are home to many traditional dishes comprised of such ingredients as wild boar, pork from the Cinta Senese pigs and hare combined with pasta, sauces or as grilled meat.  There are savory local sausages, cheese, and ribollita soup with bread, cannellini beans and vegetables.

Siena and its province also have great wines, as the area has as its neighbor the famed Chianti wine region, and where you find such famous wines as Brunello di Montalcino and Vernaccia di San Gimignano.

Traditional sweets abound for visitors with a tase for fine desserts.  These include Panforte with dried fruit and nuts, Ricciarelli almond biscuits, aniseed flavored Cavallucci, and cantucci biscuits accompanied by the dessert wine Vin Santo.

To get a sense of the local food and wine scene, consider this 2-hour food and wine tour priced at $45.42 per person, or this 3-hour educational wine tour that takes you to an organic winery in the in Tuscan hills just outside if Siena for $79.48 per person.  

Siena experienced its zenith during the medieval period of the 13th and 14th centuries when it vied with Florence for regional dominance.  Its arts flowered and its building program created the gorgeous city we know today.  But the Black Death and sieges by Florence so reduced the population and its economic resources that the city could not develop further.  

This has left today’s visitor with the amazing sensation of stepping back in time when entering the sheltering arms of Siena’s historic city center, a time capsule of the Middle Ages.  Stroll its crooked streets, eye the shops along the Banchi di Sopra, Banchi di Sotto and Via di Citta.  The city embraces its historic roots and provides a showcase of civic and religious artworks that will impress any visitor.  

Soak in the atmosphere of the Piazza del Campo and the Piazza del Duomo, pull up a ringside seat at one of the Campo’s restaurants as the setting sun lights afire the sienna colors of the Torre del Mangia and dream of the medieval age that produced such beautiful architecture and artistic treasures and whose daily life of the contradas comes alive with the celebration of the Palio twice every summer.  This city has a special ambiance to enjoy, one of the most unique in Italy.  Take the time to stay overnight and spend an extra day to truly appreciate this amazing hilltop city.  

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About the author

Lauren Juliff

Lauren Juliff is a published author and travel expert who founded Never Ending Footsteps in 2011. She has spent over 12 years travelling the world, sharing in-depth advice from more than 100 countries across six continents.

Lauren's travel advice has been featured in publications like the BBC, Wall Street Journal, USA Today, and Cosmopolitan, and her work is read by 200,000 readers each month. Her travel memoir can be found in bookstores across the planet.

1 Comment

  1. February 5, 2023

    Lauren, this is a fabulous write-up. Informative post on Siena. Such a beautiful location and I enjoyed reading this too. Keep up the good work.

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