Things to do in Siena, Italy

158 activities

Discover the Best Activities in Siena, Italy

Thanks to the semi annual Palio, Siena shares a reputation with Spain’s Pamplona for being completely crazy two days of the year and asleep the other 363. That’s really not a fair rep, though, because the Sienese provide plenty to see even when they aren’t racing bareback around Il Campo. Take the steep pedestrian-only streets of Siena’s centro, for example. The completely befuddling medieval layout is Tuscany taken to its illogical—and seriously charming—extreme. Amid the trapped-in-time Gothic architecture, you’ll find that Siena is also a respectable university town with a campus indistinguishable from the city around it—you’ll only realize you’re at the university when you poke into a church and discover it’s actually a Linguistics department. With quirky nightlife, relative freedom from overwhelming Florentine tourist crowds, and a maze of streets hiding secrets you could spend months trying to unlock, Siena is worthy of an extended stay.

Top Things to Do in Siena, Italy

Plan less, play more. Check out our recommended experiences and activities

Get to Know Siena, Italy

Your one stop resource for where to go, what to see, and how to make the most of your stay.
Produced in partnership with Let's Go! Travel Guides.

Get Oriented

The first thing you should know is that the train station is down a steep hill fairly far north of the town center. Exit the station and follow the signs to the bottom of the parking garage, where you can catch a bus to the centro—look at the digital display board to see which bus is on its way and whether it’s going where you need it to. That being said, try to arrive in Siena by bus instead of by rail. Almost all intercity buses arrive in Piazza Gramsci, in the northwest of the centro. The upper part of this piazza opens up onto Luna Park and then onto the Fortezza Medicea. Walk away from the park to head deeper into the centro, where you will soon see many Il Campo and Duomo signs, which are the best tools for navigating Siena’s labyrinth of curling dead ends and steep alleyways. Learn your way home from the Campo and these signs will be your best friend. Meanwhile, Siena’s many churches form a sort of holy compass: San Francesco is northeast, the Pinacoteca is South, and San Domenico is West.

Arts & Culture

Really, Really Old Art

One of the many things the Romans did for us was leave behind an enormous artistic legacy. They borrowed plenty from the Ancient Greeks, which meant that columns, capitals, and precise geometry were all the rage. The Roman taste for flair made its way into household art, and sumptuous frescoes of mythical stories covered wealthy Romans’ walls, while mosaics decorated the floors. Art was also used for Roman emperors’ favorite pastime: self-glorification. They commissioned as many statues and paintings of themselves as could be made, many of which can still be seen today.

Middle-Aged Art

The start of the Middle Ages was pretty lacking in originality as far as architecture was concerned. The “in” style, Romanesque, mimicked the Romans’ rounded arches, heavy columns, and windowless churches. Of course, when the new Gothic movement brought airy vaulted ceilings and giant stained-glass windows from France, the dark and heavy Romanesque style moved from the hot list to the not list. Milan’s super-pointy Duomo is one of the greatest Gothic buildings left in Italy. But despite architecture’s new and decidedly less gloomy beauty, sculptors and painters continued to specialize in dead (or dying) Christians.

Ninja Turtles Assemble

All that began to change, however, during the Renaissance. Botticelli’s The Birth of Venus, which depicted the goddess rising from a seashell, marked the beginning of a new age for painting. Michelangelo’s David, one of the most gawked-at nude statues of all time, did the same for sculpture. Michelangelo also painted the ceiling of the Sistine Chapel, arguably one of the greatest works of all time, then declared to Pope Julius II, “I am not a painter!” Fishing for compliments or not, the guy was an artistic genius. The other three ninja turtles’ namesakes, Raphael, Donatello, and Leonardo (da Vinci), also left their marks on the Italian art scene. Raphael was a prolific painter, Donatello specialized in sculpture, and Leonardo…well, the man merits a whole paragraph to himself.

Genius, artist, inventor, sculptor, and author, Leonardo da Vinci would have definitely been crowned Renaissance Man of the Century. Some of his ingenious sketches have proven to be perfectly viable plans for flying machines, testifying to their creator’s visionary imagination. The Italians weren’t always great at hanging onto his work, though, which is why you’ll have to consult Place Pass France to find his most famous masterpiece. You can see many of his paintings in Florence’s Uffizi Gallery, though, along with the renowned Last Supper fresco in Milan’s Chiesa di Santa Maria delle Grazie.

Let’s Talk About Our Feelings

By the end of the Renaissance, artists had nearly perfected the art of realistic representation. The perspective, shadow, and human figures they painted were as lifelike as any painters had yet achieved. Once this got boring, the next natural step forward was to really talk about their feelings. This new approach to painting, which focused more on sophistication and artificial representation, characterized a dramatic style now referred to as Mannerist. The most famous Italian painter of this style, Tintoretto, gained a reputation for his temper, earning himself the nickname Il Furioso.

No More Order

From this time forward, art began to move in a less uniform fashion. The Baroque style combined Renaissance grandeur with the emotional effect of Mannerism to create powerful but naturalistic works, best exemplified by Caravaggio. The sillier-looking Rococo style came a little later and focused its leitmotifs on light themes like seashells and clouds, which led to some ridiculously elaborate decorative art, particularly in Venice. The 19th century then saw two of everyone’s favorite -isms: Impressionism and Neoclassicism. The latter was particularly inspired by the interest in Ancient Rome that followed the excavations of Pompeii and Herculaneum.

The most notable 20th-century Italian movement was Futurism, which admired speed, violence, and the industrial city. Not surprisingly, many Futurists were supporters of Fascism. Recent Italian art has veered away from any particular -isms, but despite the country’s reputation for masterworks of the past, many galleries, including Venice’s Punta della Dogana and Rome’s Galleria Nazionale d’Arte Moderna, focus on works that continue Italy’s artistic legacy into the present day.

Sports and Recreation

You may (correctly) think that Italians are a pretty passionate bunch. Well, just wait until you see them at a soccer match. Modern soccer, or calcio as you should get used to calling it, is just as intense off the field as it is on. Almost every major town has a team that local residents fanatically follow. Things get really fun when a town has two major teams, particularly when those teams play against each other. In Rome, you must pledge your allegiance to either the sky blue of SS Lazio or the red of AS Roma. In Milan, the choice is either the blue and black of Inter Milan or the red and black of AC Milan. In general, it’s probably best to choose a team based on which team has more fans around you at any particular time. The top teams battle it out for the Serie A title, a competition that the Milan teams and Turin’s Juventus have dominated in the past.

Customs & Etiquette

Fitting In

A friendly bunch, Italians have their own ways of doing things. If you want to fit in, you might need a small course in Italian etiquette. Chances are, with four million visitors each year, they’ll still know you’re a tourist, but at least they’ll think you’re a polite one.

Italians place a lot of emphasis on first impressions, so don’t get yourself into a mi scusi situation. When meeting someone for the first time, a handshake is the way to go—air kissing (left side first!) generally comes with more familiarity. The Italian people are known to stand pretty close, so get ready to readjust your personal space boundaries. When it comes to clothing, Italians find having bella figura (good image) very important and tend to value quality over quantity. Short skirts and shorts are slightly more risqué in Italy than America—revealing tops are a little less so.

Tipping And Bargaining

In Italy, as in the rest of Europe, tips of 5% are customary, particularly in nicer restaurants. Italian waiters won’t cry if you don’t leave a tip—just get ready to ignore the pangs of your conscience later on. Taxi drivers expect the same kind of tip, but it is unusual to tip in bars. Bargaining is appropriate in markets and other more informal settings, though in regular shops it is inappropriate. 


It is (hopefully) not necessary to inform you that the primary language spoken in Italy is Italian. Prevalence of English-speaking varies wildly. If your trip will focus on sights like the Colosseum, you will probably be able to get by without speaking a word of Dante’s tongue. Once you head away from heavily touristed areas, however, it is much more unusual to encounter English-speakers. To attempt to initiate an English conversation, politely ask “Parla inglese?” (PAR-lah een-GLEH-zeh). Those with as much Italian experience as Dominic Decoco should endeavor to learn at least a few Italian phrases. Feel free to improvise: your high school French or Spanish knowledge might actually turn out to be much more useful than you thought. And the universal language of point-and-gesture also sometimes does the trick. Whatever the result, end your conversation with a courteous “Grazie” (GRAHT-see-yeh.)