8. Shop til you drop— Via Banchi di Sopra is the street to visit in Siena if you are looking for boutiques that sell clothes and shoes. On Friday mornings, Piazza Gramsci is occupied by a small outdoor market, where local farmers sell their fresh wares such as olive oil, bread, fruits, vegetables and cheeses. There are also beautiful local ceramics to be found around town, so keep your eyes open as you explore.
7. Visit the Museo Civico— This, the most well-known museum in Siena, is not your ordinary collection of religious medieval and Renaissance artwork. The museum was commissioned by the city’s government rather than by the church, so it covers many secular subjects, such as the virtues of a good government, Roman greats and moments in history. The frescoes in the Sala dei Nove, where the ruling council of Siena once sat, are considered among the most important secular paintings of the Renaissance.
6. Eat— La Taverna di San Guiseppe offers a divine dining experience in a friendly, unpretentious atmosphere. Try their homemade pici (like a voluptuous spaghetti) or their bistecca fiorentina, which would put any Florentine chef to the test.
5. Drink— Siena is located right in the middle of serious wine country. Enoteca I Terzi has a world class wine selection- chiantis, brunellos and much more- offered in a welcoming setting along with platters of delectable meats and cheeses.
4. Climb— If your knees will cooperate, don’t miss the Torre del Mangia. This 14th century tower is the highest in Siena, and your 400-step climb is rewarded by breathtaking views of the city and surrounding countryside.
3. Stare at the floor— Among the many wonders of Siena’s main cathedral, perhaps the most stunning is its floor. Once you get past the impressive black-and-white striped marble facade, with its high round windows that reflect the sky, you might think you’ve seen the best of what this building has to offer. But once inside, gaze downward and take in the inlaid marble mosaic floor, which tells stories and paints vivid biblical scenes. It took 2 centuries and about 40 artists to complete. But beware, much of the floor is covered for most of the year. It is unveiled for several weeks in the late summer and early fall.
2. Hang out in Piazza del Campo— My personal favorite thing to do in Siena is to just be. It’s a vibrant, beautiful city. I’ll never forget my first time there at age 22. I hopped off a bus from Florence and was awestruck by the terra cotta colors all around me. The best viewing point for life in Siena is the Piazza del Campo, a shell-shaped piazza in the center of town. There are usually many tourists around, and the restaurants and cafes on the piazza know that! But I think it’s worth the mark up to sit and sip a leisurely cappuccino.
1. Witness the Palio— If you can manage to be in town July 2nd or August 16th any given year, don’t miss the famous palio horse race. Other Italian towns have versions of a palio (a palio is simply a banner won in a competition), but Siena’s palio represents a spectacular contest steeped in generations of the city’s very serious civic pride. The 17 contrade (neighborhoods) of Siena compete in this intense and dangerous high-speed bareback horse race around the Piazza del Campo, and the winner proudly takes home the banner until next year. The race itself lasts only about 90 seconds but leaves a lasting impression on the breathless audience.