Benvenuti (welcome) to Tuscany's medieval gem. Siena is famous for its Gothic history and art, a cathedral that took centuries to build, and the Palio, a world-renowned horse race. But that's not all: the walkable hilltop city is a pleasure to explore on foot, to linger over pasta in a family-run trattoria, to taste wine in tiny shops in the historic center, and to stroll around the illuminated streets, gelato in hand, after dark. Read on for an overview of the city's top attractions and advice on where to stay and what to eat.
Interested in traveling around the region? Discover the best of Tuscany on this two-week tour.
Planning Your Visit
When to Go
Thanks to crowds—Siena is popular with tourists—and the changing seasons, there are benefits and drawbacks to visiting the city at any time of year. In summer, you'll have the chance to see the Palio, the famous horse race around the central square, Piazza del Campo. (The dates are the same every year: June 29th to July 2nd and August 13th to August 16th.) But you'll also have high temperatures and crowds to contend with. Find out more here about visiting Tuscany in August.
If you don't mind cold weather and the possibility of snow, winter is a good time to visit. Note that December is one of the busiest months for tourism in Siena, particularly around the holidays, so it's wise to reserve accommodations well ahead of time. Spring is a popular time to visit the city, too, due to the milder weather; some hotels are more expensive in May, when the city sees a spike in visitors. Read more here about traveling in the region in May. Fall is the rainiest season in Siena: pack an umbrella and take advantage of the lower prices and a relatively low number of tourists in town.
Siena is an easy train or bus ride from Florence. You could catch an hourly regionale train from Florence (the trip takes 1½ hours), though you'll have to change trains if you're traveling from Rome. Siena Mobilità runs buses directly from Rome's Fiumicino Airport (the trip takes about four hours), a handy alternative if you're flying into Italy and hoping to make a direct connection.
Find out more here about getting to Siena from Florence.
Highlights & Activities
Siena's historic center is a UNESCO World Heritage Site. Start at the Piazza del Campo, the large square that hosts the Palio horse race, stopping for a quick coffee at an outdoor café. Then tour the Duomo di Siena (Siena Cathedral), the city's top attraction. Consecrated in 1179, the Gothic cathedral took hundreds of years to build: generations of families contributed to its construction through the 14th century, and the church features sculptures by artists like Michelangelo and Donatello. If you're not afraid of heights, buy a ticket for the Porta del Cielo (Gate of Heaven) guided tour in and around the cathedral's dome. Alternatively, climb the nearby Torre del Mangia tower—it's 300 steps up, but the views are worth it.
Museums like Museo Civico, with elaborate frescoes commissioned by the city in the 14th century, and the Pinacoteca Nazionale (National Art Gallery), filed with Gothic masterpieces, offer a glimpse into Siena's rich artistic tradition. Inside the Complesso Museale di Santa Maria della Scala, a 13th-century complex across the street from the Duomo, visit the National Archaeological Museum in the underground tunnels, then stop in the onsite gift shop—it's one of the best spots in town to stock up on high-quality postcards.
Need a break from all the museums? Stop into Siena Bike Tour to rent a bicycle for a guided or self-guided ride around town, or take a stroll through the Orto Botanico dell'Università, botanical gardens run by the University of Siena. Dating from 1856, the gardens feature a citrus house, a trio of greenhouses, and beautiful views of the surrounding landscape. Then stop into one of Siena's many family-run wine shops to take a break over a glass of locally produced Chianti: two to try are Enoteca San Domenico and Enoteca Palazzo Piccolomini.
Interested in cycling in the region? Check out this five-day biking itinerary through Tuscany.
Where to Stay
Accommodations in Siena are at a premium. But many visitors pass through the city on guided tours or day trips from Florence, so if you book well ahead of time, you'll have good options. For the best sweeping views of the historic center, check out the luxurious Campo Regio Relais, where breakfast is served on a breezy terrace, or the six-room Frances’ Lodge Relais, which also features a swimming pool when the weather's warm. Borgo Scopeto Relais is another stylish option with lovely gardens, two pools, and a Vespa rental kiosk onsite.
Families might opt for rooms at the Palazzo Ravizza guesthouse, located just outside the historic center, or at a larger hotel like Garden Hotel Siena, which features a pool designed for kids. Piccolo Hotel Etruria has quadruple rooms ideal for a family of four. Apartment rentals and Airbnb properties are also solid choices in Siena, regardless of your budget or the size of your party: check out local agency Siena Apartments for listings.
Looking for a family-oriented itinerary in Italy? Check out this eight-day trip plan.
Where to Eat
First things first: Tuscan cuisine is built around local products, from excellent extra-virgin olive oil to fresh pecorino cheese to truffles collected in the forests to delicious red wines produced in Chianti. Given these outstanding raw materials, it's hard to go wrong when eating out in Siena, just as long as you steer clear of any restaurants that are clearly only catering to tourists. (A good rule of thumb here, as elsewhere in Italy, is to sit down at a trattoria, or family-run restaurant, where you see other locals eating or enjoying a glass of wine.) Classic Sienese dishes to look for include pappardelle con lepre (ribbon-shaped pasta in rabbit sauce), pici (thick spaghetti), and scottiglia (slow-cooked meat in tomato sauce).
Café-bakeries like Bar Pasticceria Nannini and Torrefazione Fiorella are great spots to start your day with Italian croissants, espresso, and ricciarelli (almond-flavored cookies). Pasticceria Buti also specializes in ricciarelli and other regional treats. Pop by Pizzeria Poppi for a quick pizza, or for a leisurely lunch or dinner, try sophisticated Salefino Vino e Cucina or Tuscan comfort food at La Sosta di Violante.
Have an aperitivo (pre-dinner drink) and a charcuterie board at the Gino Cacino, a deli offering a range of Tuscan cheeses. Taverna di San Giuseppe is notable for its food as well as its atmospheric old building you'll eat in. Tuscan-style seafood is the specialty at Osteria Castelvecchio. Afterward, stop for a gelato at Caribia.
Find out more about Tuscan cuisine here.