Past glories
These days, Florence is one of the must-sees of Italy, teeming with Renaissance masterpieces, famous sculpture and more American students than Spring Break. Any Siena local will tell you it wasn’t always the way: in the 12th century, Siena and Florence were both trying to be the numero uno city in Tuscany. Siena withstood an attack by Florence in 1230, during which dung and donkeys where flung over the medieval walls. Somehow surviving the deadly barrage of manure and flailing pack animals, 30 years later Siena had its own military triumph and ruled the roost for a decade, before being allied to Florence after a loss to Charles of Anjou. A plague in Siena in 1348 killed hundreds of thousands of citizens, setting it on a steep decline. In modern times, Siena was the first European city to ban cars from its city centre in 1966 and has since witnessed a strong tourism resurgence as visitors rediscover its Gothic charms.

Off and racing
Siena’s Il Campo has to be one of the most beautiful squares in Europe. On July 2 and August 16, gutsy Italians race horses around it in a spectacular and at times violent spectacle of colour and chaos. Il Palio has its traditions rooted in the Middle Ages and pits 10 of the city’s 17 contrade (districts) against each other in a festival of racing, boozing and eating. And the best bit? Even if a jockey falls, the horse can still win. The town’s limited accommodation fills up quickly, so book early.

On your bike
Cycling around Siena and its car-free city centre is a perfect way to explore the town and work off some of those pizza-induced love handles. Most of the farmhouse-style accommodation ringing the town has bikes for hire, and while the cars can zip a bit close for comfort on the way into town, a leisurely pedal around the maze of medieval streets is well worth a close call or two.

WORTH A LOOK

Il Campo
The campo is the city’s focal point and anchors a maze of narrow streets that wind our from its flanks. Palazzo Comunale (town hall) and its towering, postcard perfect clocktower soar over the square, which is usually covered in visitors lunching at cafés, taking in the sights or soaking up some sun.

Cathedral
Siena’s cathedral on the Piazza del Duomo is one of the country’s finest examples of Gothic architecture. If you’re too churched out to line up and duck inside, meandering through the medieval-walled streets of the city on the way there is a pleasure unto itself. Amen to that.

Bonus points for: Charms the pants off Florence.
Loses marks for: Hostels fill fast in peak times.
Check out: www.terresiena.it