(This is part of our series of posts from our six-week Road Scholar Independent Living and Learning in Florence trip to Italy in Spring 2025. We have an index to all the posts from that trip here.)
Going on only five hours of sleep after our late night Friday at the birthday/farewell party, we still made it to the Florence train station at 8:30 Saturday morning for a school-organized trip to Siena. As with all the other tours and programs organized by the language school, it was conducted entirely in Italian, which gave us plenty of practice in listening and speaking. Siena was stunning and the weather was perfect, so we were glad we didn’t decide to skip the tour!
On the train for the 1 1/2 hour journey to Siena. (It’s not that far, but there is no direct “fast train” service from Florence, just a regional that makes stops along the way.) It was still cool enough in the morning that we needed sweaters!

Like many old Tuscan cities, Siena was built on a hilltop for defensive purposes. The modern city, which you can see in the middle of the photo, has grown up around the hill. A series of escalators and moving ramps–“scale mobile” in Italian–in the brick enclosure in the foreground makes it easy to get up to the old city.

This sign on the observation terrace at the top of the scale mobile demonstrates that you can convey your message effectively without any words.

The Porta Camollia, one of the medieval gates around the walled city of Siena, dates back to at least 1082, but it was substantially rebuilt in 1604. Siena is a VERY old city.

It doesn’t get more classic than this Italian scene: a vintage Fiat 500 in front of a medieval church.

The gray building at the back of Siena’s Piazza Salimbeni is the original headquarters of Monte dei Paschi. This was the world’s first bank building, built in 1472. Before then, banking transactions were conducted in market stalls. Monte dei Paschi is still in business–they have branches throughout Tuscany–and the bank still uses this building, although it’s no longer their headquarters. The statue in the piazza honors Sallustio Bandini (1677-1760), a Sienese archdeacon, economist, and politician who was an early advocate of free trade and removal of local feudal tariffs and tolls.

The building on the right side of Piazza Salimbeni has busts of notable people along its cornice, including this one of Dante Alighieri (center).

The Piazza del Campo is regarded as one of Europe’s greatest medieval squares, renowned worldwide for its beauty and architectural integrity.

The enormous Piazza del Campo is much larger than typical medieval standards of the time, but it was large enough to hold the entire population of Siena when it was built–about 50,000 people. The campo was and still is the focal point of public life in the city.

A horse race called the Palio is held twice each summer in the Piazza del Campo in a tradition dating back to the 17th century. Ten horses ridden bareback by jockeys run three laps around the perimeter of the dirt-filled piazza. The Palio is a fierce competition between the contrade, or city wards. Although the race itself lasts only about 90 seconds, it is surrounded by several days of pageantry and celebration.

Our tour group in Piazza del Campo. These are language students from all over the world; we were the only ones from the Road Scholar program.

Arches over a narrow side street in Siena.

The Baptistry of San Giovanni, part of the Siena Cathedral complex, was built between 1316 and 1325.

Climbing the steps from the Baptistry up to the Siena Cathedral. Did I mention that old Siena is built on a hilltop? The hills continue throughout the city, so we did a lot of up-and-down walking.

The Siena Cathedral is a medieval church founded circa 1100 CE, making it even older than the city of Florence. The current structure was built on the original site between 1215 and 1263. The granite façade, designed in the cityâs colors of black and white, wasnât completed until almost 100 years later.

After a group lunch, we returned to visit inside the Siena Cathedral. The interior was just breathtaking. The theme of black & white granite, representing the city’s colors, is carried into the interior, forming dramatic stripes on nearly every vertical surface.

One of the many famous features of the Siena Cathedral is its marble floor, which is inlaid with multiple colorful mosaics. This one–“The She-Wolf Suckling Romulus and Remus”, or The She-Wolf of Siena, was originally created in the 1360s but heavily restored in 1865. It portrays a wolf, suckling Romulus and Remus, in the center, surrounded by eight smaller circles, each depicting the emblem of major rival Italian city-states.

Another inlaid marble mosaic on the floor of the Cathedral, “The Slaughter of the Innocents”, created in 1484â1485 by Matteo di Giovanni.

The horizontal molding around the nave and the presbytery of the Cathedral contains 172 plaster busts of popes dating from the 15th and 16th centuries, starting with St. Peter and ending with Lucius III.

A closer look at the altar & presbytery of Siena Cathedral.

The Gothic-style pulpit, sculpted in Carrara marble in 1265-1268, is the oldest remaining work of art in the Cathedral.

Interior of the dome of Siena Cathedral, decorated in blue with golden stars, and with an oculus at the top to let in natural light.

Just off the main sanctuary of the Cathedral is the Piccolomini Library. It was commissioned in 1492 to be the repository of the book collection of Cardinal Enea Silvio Piccolomini, who eventually became Pope Pius II.

The frescoes on the walls of the Piccolomini Library depict important scenes from the life of Pope Pius II.

Although most of the original books from the Piccolomini Library are now lost, today the room is lined with a collection of beautifully illuminated Psalters from the mid-1400s.

After our walk through Siena, it was time for a little fortification with a coffee and a pastry from Cafe Nannini, a pasticceria that at least two people told us we couldn’t miss. The oval-shaped cookie is a “ricciarello”, a moist almond-flavored treat native to Siena.

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