Since the 11th century, the Sienese have conducted festivals every year where the contrade compete for renown (and in times gone by, actual political power) through contests such as flag throwing, horse racing and even fist fights. The fist fights no longer happen (a heavy police presence in the weeks prior to the contest sees to that), but the spirit of competition between contrade is still fierce. The race itself is in late evening but the whole day of the race is taken up with processions through the streets of the various contrade competing in the particular race (only ten can compete at any time for safety reasons).

Classical concerts during the summer at the Accademia Musicale Chigiana, and at various locations in the city during the Settimana Musicale Senese. Siena Jazz Festival during summer.

Walk

Climb the “Torre del Mangia”, the tall bell tower overlooking the Piazza del Campo. There is an entrance fee, and only 25 people are let in at a time, so there may be a wait. Not for the faint of heart or claustrophobic, it’s about a 300 step hike and you are obliged to leave bags and purses in a locker at the ticket desk inside the tower itself. The panoramic view is exhilarating and well worth the climb.

Local life in the evening typically revolves around the Passeggio, the nightly walk through town, which often includes some gelato, macedonia di frutta con gelato, or/and drinks at one end or the other. So do as the locals do and enjoy a walk through this beautiful city.

Tours
Take a tour of an Etruscan tomb, visit a winery for a wine tasting, sample regional food, and visit a local village. There are many such tours available.