by Celeste Lipford and Terry Lipford - last updated on 5/21/2025
Siena is a city in Tuscany, Italy and it is the capital of the province of Siena. The historic centre of Siena has been declared by UNESCO as a World Heritage Site. It is one of Italy's most visited tourist attractions, with over 163,000 international arrivals in 2008. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race ("Palio di Siena") held twice a year. During our pre-trip research, we had read about this horse race and since the race would be held while we were in Florence, we knew that we had to schedule a day trip to Siena to see this famous race.
Visitors to Siena may find navigating the city challenging due to its medieval layout, narrow streets, and hilly terrain. The city’s historic center, a UNESCO World Heritage Site, is characterized by winding, cobblestone streets that were designed centuries before modern transportation, resulting in limited access for cars and a maze-like atmosphere that can be confusing for new visitors.
The city’s main square, Piazza del Campo, serves as a central reference point but does not align in a grid pattern with surrounding streets. This can add to the confusion, as landmarks may appear hidden within the city’s intricate layout. Despite the challenge, however, getting “lost” in Siena can be part of the charm, leading visitors to discover hidden courtyards, quaint shops, and unique views along the way.
Click here to view the Siena Wikipedia Page for a more complete description of the Palio di Siena.
Exploring SienaOnce we were able to get clear of the Florence City traffic, we headed straight south on the Raccordo Autostradale Firenze for approximately 80 kilometers (from Porta Romano near our condo rental). Our primary concern was to get to Siena "early enough" to find a parking place, as we knew that there would be a very large crowd for the horse race.
Siena is a quintessential Italian city where the charm of history seamlessly coexists with the vibrancy of modern life. Over time, a newer, more contemporary part of the city has developed, encircling its ancient core like a protective embrace. At the heart of the historic district lies the Piazza del Campo, a breathtaking medieval square that serves as the stage for the world-famous Palio di Siena horse race. This captivating tradition, steeped in history and local pride, makes the older part of Siena a must-visit destination.
However, as with many historic cities, navigating Siena presents its own set of challenges — particularly when it comes to parking. The narrow, winding streets of the old town, originally designed for foot traffic and horse carts, are not exactly car-friendly. For us, the challenge was finding a parking spot close enough to the historic center to allow us to comfortably walk to Piazza del Campo.
We quickly realized that parking in Siena requires a bit of patience and planning. The modern outskirts of the city have several parking lots and garages, some within walking distance of the old town. After some searching, we managed to find a spot just outside the historic zone, leaving us with a pleasant walk through Siena’s cobblestone streets.
That walk itself was a treat. Passing by ancient buildings, picturesque alleyways, and charming shops, we felt as if we’d stepped back in time. As we approached Piazza del Campo, the city’s rich history became even more palpable, with its iconic shell-shaped square opening up before us in all its grandeur. The anticipation of seeing the site of the legendary Palio made the effort of finding parking more than worthwhile.
Piazza del CampoEven though we had arrived in Siena early in the morning, the energy of the city was already palpable. People were beginning to gather in anticipation of the Palio di Siena, and the atmosphere buzzed with excitement. The heart of the event, the Piazza del Campo, had been transformed into an arena for the famous horse race. This iconic square, circular in design with its unique shell-shaped layout, was meticulously prepared for the spectacle. Temporary stadium seating and standing-only areas had been marked off all around the perimeter, creating an amphitheater-like setting.
Unfortunately, all the seating was long since reserved, and as we learned, tickets were not only difficult to come by but also prohibitively expensive. Even the standing areas, which were open to the public, were quickly filling up. Despite our early arrival, it was clear that claiming a spot for the race would require committing to an entire day of waiting under the summer sun.
After a brief discussion, we weighed our options. The race itself wouldn’t begin until late in the afternoon, meaning hours of standing shoulder-to-shoulder with the growing crowd. With no place to sit and little hope of securing a comfortable vantage point, we made the practical yet bittersweet decision to forgo spending the day in Siena. Instead, we set our sights on a new adventure — heading east to explore Italy’s Adriatic coast.
Before leaving, we took advantage of the time we had by wandering through Siena’s enchanting streets. As we meandered back toward our rental car, we found ourselves immersed in the city's medieval charm. The narrow cobblestone alleyways, vibrant window boxes bursting with flowers, and small artisan shops offered a quiet contrast to the bustling Piazza del Campo. It was a reminder that Siena’s beauty goes far beyond the spectacle of the Palio.
Porta CamolliaPorta Camollìa is one of the northern portals in the medieval walls of Siena. It is located on via Camollia and opens inside the city into the Contrada of Istrice. It consists of three arches; the inner arch is surmounted by a circular marble bas-relief with the Roman Catholic IHS Christogram inside a sun symbol (San Bernardino Christogram). The outer facade has the Medici heraldic shield with a stone arch added in 1604 by Alessandro Casolani and decorated by Domenico Cafaggi. The inscription was placed to record the entry of Ferdinand I de' Medici into Siena, and states Cor magis tibi sena pandit (Siena shows a heart that is bigger than this gate). The two central figures hold the Medici coat of arms.
Siena CathedralSiena Cathedral, or Cattedrale di Santa Maria Assunta, is a stunning medieval church in Siena, Italy, originally dedicated as a Marian church and now honoring the Assumption of Mary. This architectural masterpiece, completed between the 13th and 14th centuries, served as the episcopal seat of the Diocese of Siena before becoming the Archdiocese of Siena in the 15th century. Today, it remains the seat of the Archdiocese of Siena-Colle di Val d’Elsa-Montalcino.
The cathedral is celebrated for its striking Gothic architecture, with a façade of intricate marble in black, white, and red hues symbolizing Siena's civic identity. Inside, visitors are awed by the elaborately decorated mosaic floor, vibrant frescoes, and works of art by renowned artists such as Michelangelo, Donatello, and Bernini.
The cathedral complex also includes the Piccolomini Library, home to exquisite frescoes by Pinturicchio, and the unfinished New Cathedral, which adds historical intrigue to its story. Siena Cathedral stands as a symbol of the city’s medieval grandeur and remains a significant pilgrimage site, blending religious devotion with artistic splendor.
Departing the Piazza del CampoSince the horse race was still many hours later that day, we decided that we were not going to wait, so we researched our maps and decided to drive over to the coastal area of Italy near Livorno.
We decided to take a scenic drive north along the Raccordo Autostradale Firenze, a route that promised breathtaking views and a chance to explore some of Tuscany’s most iconic destinations. Our plan was to visit the Castello di Monteriggioni and then continue to San Gimignano before making our way to the Livorno area. While it might sound like a lengthy journey, the entire route is only about 135 kilometers, making it a manageable and incredibly rewarding day trip.
Castello di MonteriggioniThe circular walls of the castle, totalling a length of about 570 metres and following the natural contours of the hill, were built between 1213 and 1219. There are 14 towers on square bases set at equidistance, and two portals or gates. One gate, the Porta Fiorentina opens toward Florence to the north, and the other, the Porta Romana, faces Rome to the south. The main street within the walls connects the two gates in a roughly straight line.
Image Credit: Above image is the property of Maurizio Moro5153 via Wikimedia Commons using the CC BY-SA 4.0 license
As we drove north on the autostradale Firenze (Florence Freeway), we spotted the sign for the Museo Delle Armature in Monteriggioni - which not only looked like an interesting place to visit, it also had a place where we could get coffee & snacks and restrooms!
The Museo delle Armature (Museum of Armor) in Italy, located within the historic Rocca di Angera fortress near Lake Maggiore, offers a fascinating glimpse into medieval warfare and chivalric culture. The museum houses an extensive collection of delle armature (armor) that dates back to the Middle Ages and Renaissance, showcasing the craftsmanship, materials, and designs used to protect knights and noble soldiers in battle.
Visitors can view a variety of pieces, including full suits of armor, chainmail, helmets, shields, and weaponry like swords and lances. Many of the armor sets are elaborately designed, with intricate engravings and decorations that highlight the artistry of the time and indicate the rank or family of the wearer. The armor ranges from practical battle gear to ceremonial pieces worn during tournaments or parades.
The museum's layout and lighting enhance the dramatic presentation of the armor, allowing visitors to appreciate the detail in each piece and to imagine the history behind them. This collection is not only a display of military equipment but also an insight into the social and cultural significance of knighthood in Italian history.
The kids had a great time investigating various displays in the museum, because the Museum allows handling and wearing some weapons and parts of armor, located in special areas . Some explanatory panels and an easy multilingual audio guide accompany the visitor on this short but intense immersion in history.
The really interesting thing about this museum and their collection of armor, was that we were allowed to try various pieces on, and to interact with all of the displays. Very cool, and something that you just do not see in an American Museum.
I had just finished explaining to the kids that medieval warriors and soldiers often relied on a "fierce appearance" to intimidate their enemies on the battlefield. Their armor, weapons, and even their expressions were designed to strike fear into the opposition. Naturally, when Mom suggested snapping a picture of them in this part of the museum, they couldn’t resist putting on their best "fierce warrior" poses!
With serious expressions, raised fists, and dramatic stances, they channeled their inner knights and warriors, fully embracing the moment. Their efforts to look intimidating were equal parts amusing and impressive — it was hard not to laugh at their exaggerated determination while appreciating their enthusiasm. Surrounded by displays of ancient swords, shields, and suits of armor, they truly looked like they belonged in a scene from a medieval epic.
The museum setting added to the authenticity, with its dim lighting and towering exhibits casting dramatic shadows that made their "warrior mode" even more believable. It was a playful moment that brought history to life in the most fun and memorable way. The photo we captured that day perfectly embodies the spirit of our visit: equal parts learning, laughter, and a little bit of theatrical flair!
The Castello was built by the people of Siena at the beginning of the 13th century, to watch over the valleys extending towards their rival town, Florence, in 1554 the Monteriggioni Castle was conquered by the Florentine Medici family. After so many wars, the castle changed hands not after a battle, but because of treason by a false ally, Bernardino Zeti.
The entire castle structure and surrounding buildings looked as though they had been there for a seriously long time and looked every bit the part of a castle or fortified structure. Fortunately for us, it also had an espresso bar and a cold drinks machine.
Our next stop on the way to Livorno, would be Castel San Gimignano. Astute map reading and investigative use of our Italy guidebook led us to this decision.
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Siena Tours via GetYourGuide
