First Place to Visit in Tuscany: Sienna, Frozen in Time

Start your Tuscan adventure in Sienna, Florence’s rival city, now frozen in time. Surrounded by olive groves and the vineyards of Chianti, Siena is one of the most beautiful cities of Tuscany. Set on three hills, the city is connected by winding alleyways and steep steps.

Like other Tuscan hill towns, Sienna was first settled by the Etruscans (in 900 BC to 400 BC). Centuries later, in 30 AD, the Romans established a military outpost in Siena. The town developed into a busy little trading post, advanced by the Via Francigena—the trade and Pilgrim road linking Rome to France—that greatly increased Siena’s importance.

Sienna grew in economic and military power to become a major and powerful city of 60,000, equal in size and importance to Florence. Like Florence, Siena commissioned great artists to create beautiful monuments and artwork as evidence of its stature.

But Sienna’s golden age ended abruptly with the devastating plague that swept through Italy, France, Germany and other European countries, spread by infected fleas carried by black rats. Around 1/3 of the population of Europe died in this plaque. When the plague hit Siena in 1348, it killed its victims almost instantly…the ill would “fall over dead while talking.” There were so many deaths that some believed this to be the “end of the world.”

Fervent friction developed between Sienna and Florence as they recovered from the plague, with both cities determined to enlarge their own territories at the other’s loss. Siena won some of the many battles between the two cities. But eventually Florence gained the upper hand in 1555, in alliance with the Spanish crown. Siena surrendered to Spain and the Spanish king ceded Sienna to Florence to pay off his huge debts to the Medici family.

Start by Locating Piazza del Campo

In Sienna you will have your opening experience with a grand Piazza, Piazza del Campo, standing at the heart of the city. Find the Fountain of Joy and the statue of Venus for up-close looks. This vast open space was once the center of commerce and the scene of executions and bullfights. Now it is home twice a year to the famed Palio—the bare-backed horse race where the 17 neighborhoods (“contrade”) compete fiercely to win the highly-coveted banner. The Palio race lasts only one minute, with three laps around the piazza, and is attended by 60,000 wildly cheering viewers.

Take Your Time Visiting the Duomo that Took Centuries to Complete

Also, you will take in your first excessively resplendent Duomo, with its gold-leaf fresco and façade of pink, white, and green marble. Take time to study closely the 56 masterpieces  embedded in the floor panels, depicting stories of legend, fortune, journeying, wisdom and rape. If you are in Siena on a Wednesday, take in the weekly market. And consider signing up for the 2-hour class at the Tuscan Wine School near the Duomo to begin your introduction to Tuscan wines.

Sienna Duomo

Coming next…

On a day trip from Sienna, venture by train to little San Gimignano