Things to Do in Siena
Things to Do in Siena

Ultimate Siena Things To Do Travel Guide

One of the crown jewels of Italy’s region of Tuscany is the magical medieval city of Siena. Once a great European powerhouse in the early thirteenth century, the city is now much smaller than modern day Italian metropolitan areas such as Milan. Though the city is still estimated to receive virtually thousands of visitors each year, it maintains a trace of anonymity which affords visitors a less crowded and often more peaceful experience when it comes to exploring the local attractions. Whether it is for the day or for several, the lovely city of Siena is a more than worthwhile addition to your Italian vacation itinerary.


Although there are a number of festivals and events that take place annually in Siena, none draw the enormous crowds or measure up to the multi-day pomp and circumstance of the Palio. The Palio di Siena is a historical horse race with medieval origins that still occurs in Piazza del Campo to this day. Traditionally, the Palio is held twice each year on July 2 (which is the Feast of the Visitation and the Feast Day of the Madonna di Provenzano) and on August 16 (in honor of the Feast of the Assumption), though an additional Palio may be held during the year between the months of May and September for special events or celebrations, such as the 100 year anniversary of the conclusion of World War I in 2018.

The horse race is a competition between the contrade, or the districts of the city. Siena’s historical city center is divided into seventeen districts, each with its own colors and symbol. During the days leading up to the Palio, Piazza del Campo is transformed as the track is laid in the square and stands are prepared for the seated spectators. All through the streets of the historical city center you will find flags and banners waving with the symbols and colors of the contrade. Additionally, locals will wear the scarves and colors of their contrade as they go about their daily business around the city.

The contrade have illustrious histories and originally there were more than 50 contrade in the city of Siena. These districts are governed by councils that organize activities throughout the year. Contrada affiliation in Siena is taken very seriously even today, with members of a contrada being akin to members of a family.

Ten of the seventeen contrade compete in each Palio race, and there is a drawing of lots to determine three of the teams that will race (the other seven teams correspond to the contrade that did not race in that month’s Palio the previous year). Three days before the Palio, lots are also drawn to determine which horse will be assigned to which team. Once the horses are assigned, there are a series of trial races that occur over the following days, culminating with large outdoor dinners held by each contrada on the evening before the Palio. During the dinner, the head of the contrada and the jockey make enthusiastic speeches and the members of the contrada sing their district’s hymn.

The morning of the Palio is steeped in tradition, with each contrada holding a mass to bless their jockey followed by a blessing of the horse. Next is the magnificent procession through the city all the way to the Piazza del Campo, featuring drummers and flag-throwers with participants dressed in historic costumes. At this point, Piazza del Campo is filled with cheering spectators as the horses line up on the starting line. Attendees are encouraged to secure their spot early. If you hope to attend the Palio during your visit, speak to Trips 2 Italy about making plans in advance since the festivities are known to attract thousands of spectators, with seated tickets selling out well before the event.

The horse race itself consists of three laps around Piazza del Campo and typically lasts no more than 90 seconds. It is interesting to note that the horses, not the jockeys, are the true stars of the race. In fact, a horse does not need a jockey to be victorious, and the first horse to cross the finish line at the end of the third lap, with or without their jockey, is declared the winner. The winning contrada is awarded the prestigious Drappellone or Palio, a silk banner that is uniquely designed each year, and the prize is proudly displayed in the winning contrada’s museum.


One of the most stunning areas of the historic center of Siena is its old world Piazza del Campo. This enormous square transports visitors back in time with its large open cobblestone gathering area, buildings featuring Gothic architecture, and the tower of the Palazzo Pubblico. This square also features a famous marble water fountain (Fonte Gaia) that is often a central meeting place for locals and travelers alike. The Piazza del Campo is a perfect place to people watch and enjoy a cool drink.

Siena’s Fortezza Medicea (Medici Fortress) is a popular location for locals and travelers alike. This historic fortress that dates back to the sixteenth century was built by Florentine forces to maintain control over Siena. Today the area is typically quite peaceful and offers wonderful panoramic views of the city if standing upon the fort’s bastions. The fort also features a striking garden area for guests to walk through. It is not unusual for local festivals or concerts to be held at the Medici Fortress. Additionally, the structure is home to an Enoteca, where visitors can learn more about local wine production and purchase wines from the province of Siena.

As in other parts of Italy, weekly and monthly outdoor markets are known to pop up throughout Siena. Most of these markets feature a wide variety of wares from antiques to clothing and accessories to décor and food products. Before arriving in Siena, speak with your Trips 2 Italy travel specialist about which outdoor markets will be operational during your stay there. These markets can be an excellent place to shop for souvenirs as well as possibly taste test a few local foods.

An interesting relic of Siena’s medieval past is Fontebranda, which was built during the thirteenth century. This beautiful fountain with Gothic arches once distributed water throughout the city, providing drinking water as well as water to wash textiles. Today the water continues to flow from the ancient aqueducts and the fountain is home to many fish.


The city’s most important church is the Siena Cathedral. This circa thirteenth century structure is grand inside and out, featuring the white and black marble striping representing the symbolic colors of the city that are also featured on Siena’s coat of arms. For many guests, the highlight of the cathedral is the fifty-six inlaid marble floor panels that were designed by various artists depicting allegories and stories from the Old Testament. Completed over a period of two centuries, the floor artwork is very fragile and therefore covered for the majority of the year in order to protect it from damage. During certain periods of the year, the entire floor is uncovered for visitors to admire its full glory. Outside of these periods, only small portions of the floor are left uncovered.

Another destination to visit when admiring the Siena Cathedral is the Piccolomini Library. The library is located inside the Duomo and features astonishing and colorful frescoes that are estimated to date back to the early sixteenth century. Frescoes cover the walls of the library, but most guests are taken aback by the intricately detailed and gold accented frescoes of the room’s vaulted ceiling.

The Museo dell’Opera del Duomo is filled with artistic treasures related to the Siena Cathedral and its history. Here guests can view many of the art masterpieces and statues that were once originally intended for a grander version of the local cathedral. When visiting, don’t forget to go up to the top of the building for a memorable view of the beautiful cathedral and stunning city.

Also not to be missed during your stay is the Siena Civic Museum, which is located inside the Palazzo Pubblico in Piazza del Campo. Guests visiting the museum are treated to a history of the city as well as some of the city’s most notable artifacts and artwork.

An intriguing place to visit in Siena’s historical city center is the Ospedale di Santa Maria della Scala (Santa Maria della Scala Hospital). This complex was one of the first hospitals in Europe and its mission was to care for the city’s poor and sick as well as abandoned children. Today it is a large museum renowned for its frescoes, altar pieces, historic chapels, sculptures, and archeological artifacts.

One of Siena’s holiest sites, which attracts pilgrims from around the world, is the Sanctuary of St. Catherine, the patron saint of the city. The sanctuary includes the former house of St. Catherine and features the cell of the saint as well as the crucifix from which St. Catherine is believed to have received the stigmata.

The Basilica of San Domenico is one of the most important churches in Siena, with rich historical significance. Construction originally began in 1226, but was later enlarged, giving it a Gothic appearance. The church has withstood a variety of damaging events through the centuries, including military occupation, an earthquake and several fires. The stunning interior contains relics of St. Catherine, as well as several famous works of art portraying the city’s patron saint. Some of these works include the Canonization of St. Catherine by Preti, St. Catherine’s Exorcism by Vanni, and Nativity of the Virgin by Casolani, along with many others.

Another favorite spot for visitors is the Baptistery of St. John. While the church was built in the early 1300s, the façade was never completed, yet the interior is filled with exquisite Sienese art and lavish decorative touches. The famous baptismal font is a work of art in itself. The baptismal is hexagon in shape, carved out of marble, and features sculptures depicting important scenes from St. John’s life. There are a number of stunning artworks dedicated to the life of the saint within the church.

For more exciting art and fascinating history, a visit to Pinacoteca Nazionale, or the National Gallery is a must. The gallery is found in two Gothic palaces within the city center. In the true style of Sienese art, you will find a variety of works featuring fantastic golden backgrounds and accents. Some of the works housed in the gallery include St. Peter Enthroned by Guido da Siena, and Adoration of the Magi by Bartolo di Fredi.


There is something inherently beautiful about the medieval city of Siena. Capitalize on this charming ambiance by simply wandering the steep and winding streets of the city to discover hidden treasures. From the wide open spaces of city squares to the enchanting and whimsical side streets, visitors can find quaint cafes, go shopping in boutiques, and revel in the everyday culture of this quintessential Italian city.

There are several small parks located throughout Siena. Some of these parks feature play equipment while others just offer a peaceful oasis complete with beautiful vegetation and cozy park benches. An afternoon at the park can do wonderful things for a family: the children can play while the adults rest and daydream about their plans for the rest of the day.


The Torre del Mangia is one of the top attractions within Piazza del Campo, and for good reason. This singular tower stretches over two hundred and eighty-five feet into the air, in a city that sits upon three hills in the Tuscan countryside, making it quite a sight even from a distance. If the kids are looking to burn off a little energy, consider climbing the estimated four hundred steps inside the tower with them. Visiting the Torre del Mangia is a good way to get in some exercise, and the view from the top offers breathtaking scenery of Siena and its surrounding areas.

After leaving the Torre del Mangia, if the kids still have any energy left, the Piazza del Campo’s wide open space lends itself for the children to run and play. It is not uncommon to see young children playing a game of tag in the expansive square.

Pack your bags and head to Italy to find what exciting activities await you in medieval Siena. Whether you are vacationing for your honeymoon, as a family, or even a girls’ trip, Siena is a lovely city with something for everyone.