Siena Secrets: 17 Things To Do In Siena

Last Updated on November 5, 2025 by spritzience

A Tuscany Escape Full of Art, Cars, and Cobblestone Charm

If you’re planning your dream Italy trip, let me offer a tip straight from a New Yorker who’s called Milan home for 10 years: Siena Italy is one of the most soul-stirring cities in the country—and easily one of the most rewarding spots on any Tuscany travel itinerary. Whether you’re into medieval history, Gothic cathedrals, quiet gardens, or vintage cars roaring through Renaissance piazzas, there are so many unforgettable things to do in Siena that you’ll want to linger longer than a day.

Technically, you can visit Siena as a day trip from Florence, Rome, or even Milan. But trust me—it’s best savored slowly, ideally with an overnight stay (or two). I visited Siena this past June while chasing the legendary Mille Miglia rally across Italy, and once those classic cars zipped past the sun-drenched buildings and flag-festooned alleys, I knew I had to stick around.

Siena isn’t just a city—it’s an experience. One that made me wonder, how had I missed out on visiting the museums and really exploring this city before? Why did I only have eyes for the famous Palio? Come along with me as I share the favorite things I discovered exploring an incredible town where cobblestones, cappuccinos, and centuries-old pageantry collide in the most enchanting way.

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1. Soak In The Magic Of Il Campo

Start your Siena adventure in its most iconic space: Piazza del Campo, affectionately known as Il Campo. Unlike your typical town square, Il Campo is shaped like a fan or a seashell, gently sloping downward toward the Palazzo Pubblico and Torre del Mangia.

It’s not just the visual drama that makes this space one of the best things to do in Siena—it’s the atmosphere. This is where locals gather, lovers lounge, students sprawl out on the bricks, and historic horse races (yes, actual ones) still tear through twice a summer during the famous Palio di Siena.

At the upper end of the piazza, don’t miss the Fonte Gaia—a white marble fountain that gleams in the sun like a Renaissance jewel. Installed in 1419, the name means “Fountain of Joy,” and it originally celebrated the arrival of clean water to Siena via a complex medieval aqueduct system.

The original sculptures were carved by Jacopo della Quercia, a major influence on Michelangelo. While the current version is a 19th-century replica, you can see the originals at the Santa Maria della Scala museum. Fonte Gaia is more than just a pretty photo spot—it’s a triumph of engineering and artistry that shows just how advanced Siena was in its heyday.

☕ Spritzience tip: Grab a coffee or aperitivo from Bar Il Palio, sit on the warm red bricks with your back against the Palazzo, and people-watch to your heart’s content. It’s a postcard moment, elevated.

📸 Italy aesthetic tip: Il Campo is also the perfect spot for Siena night photography—especially when the piazza empties and the lamplight glows on the stones.

2. Climb The Torre del Mangia For A Jaw-Dropping View

If you’re building your Italy bucket list, this one’s a no-brainer. The Torre del Mangia is not only one of the most recognizable landmarks in Siena Italy, it’s also one of the most rewarding climbs in all of Tuscany Italy—and that’s saying something.

Standing tall at nearly 102 meters (334 feet), the tower was constructed between 1338 and 1348 and strategically placed right on the edge of the Palazzo Pubblico, Siena’s elegant town hall. This wasn’t just architectural flair—it was a bold political statement. At the time, Siena was a fiercely independent republic, and building a secular tower just as tall as a cathedral’s campanile was the city’s way of saying, “Our government matters just as much as our church.” That kind of confidence is part of what makes the Siena Italy background so fascinating.

You can climb the tower for €10, or get a combined ticket that includes entry to the Museo Civico and other nearby attractions for even better value. It’s 400 steps up a narrow spiral staircase, so bring comfortable shoes, a little patience, and a fully charged phone because the Siena cityscape that awaits you at the top is the stuff of postcards and Pinterest boards.

From up there, you’ll get a sweeping view of Il Campo, the striped marble spires of the Siena Cathedral, and the undulating green hills of Siena Tuscany stretching toward the horizon. It’s the perfect moment to breathe in the medieval majesty and snap some once-in-a-lifetime Italy photography.

🎟️ Ticket tip: You can purchase entry at the Torre itself, but in peak season, it’s wise to book ahead online—as tickets sell out – many people consider this one of the best things to do in Siena. Only small groups are allowed at a time for safety.

📸 Italy aesthetic tip: If you’re up for early-morning light, try the first time slot—it’s quieter, cooler, and the rising sun over Toscana Italia is pure magic.

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3. Uncover Hidden Masterpieces At The Museo Civico

This was one of my absolute favorite things to do in Siena—a quiet treasure that surprised me with just how immersive and emotionally rich it felt. The Museo Civico, located inside the Palazzo Pubblico right on Piazza del Campo, might not get the same buzz as the Uffizi or the Vatican Museums, but it’s honestly one of the most visually powerful places I’ve ever stepped into.

From the moment I entered, I was floored by the rooms themselves—ornate, layered, and loaded with history. Every space is dressed to impress, with large frescoes, colorful murals, towering painted ceilings, chandeliers, and oil portraits watching you from across the centuries. It felt like I was walking through a time capsule, one that hadn’t just been preserved, but still buzzed with civic pride and drama.

I could practically imagine the magistrates sitting in these very halls, robed and serious, while other officials darted between rooms making decisions that shaped Siena, Italy for generations. The Sala dei Nove (Hall of Nine) was a particular standout for me—with Ambrogio Lorenzetti’s Allegory of Good and Bad Government stretching across the walls in thought-provoking detail. It’s a 14th-century fresco cycle that still feels eerily relevant. Justice, tyranny, prosperity, and decay all play out in vivid, allegorical form.

One detail I adored? Along the medieval windows facing Il Campo, you’ll spot carved-out stone ledges where a lucky few used to stand and watch the Palio—one of the most unique things to do in Siena. Imagine having that view of the most electrifying horse race in Tuscany Italy.

Another unique item, is the golden she-wolf. You’ll see various references to her throughout Siena, as she has been used as symbol of Siena to help remind people of the legendary Roman origins of Siena. This she-wolf has enamelled Sienese coats of arms to represent the different sections of the city and military allies.

There’s also a mini climb (just a few manageable staircases!) that takes you up to one of the tower’s outer galleries, offering gorgeous views over the rooftops and out toward the Sienese countryside. Honestly, it was the perfect compromise for those of us visiting in peak summer who want the view without climbing all 400 steps of the Torre del Mangia. I was hot, mildly dehydrated, and still thrilled by the panorama.

📸 Italy photography bonus: Step onto the balcony or near the upper windows for some stellar wide-angle shots of Siena Tuscany—especially at golden hour when the terracotta rooftops are glowing.

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4. Marvel At The Siena Cathedral (Duomo di Siena)

I’ll be honest—most of the time, I don’t pay to go into churches. In Italy, you’re surrounded by so much spiritual beauty that it’s easy to admire from the outside, snap a photo, and move along with your gelato. But the Siena Cathedral—or Duomo di Siena—is an entirely different experience.

It’s not just a church; it’s a full-blown art museum wrapped in black-and-white marble stripes and jaw-dropping detail. After exploring every corner, I can honestly say this: if I had skipped it to save a few euros, I would’ve seriously missed out. This is one of the most spectacular things to do in Siena, period.

Built in the 13th century, the Duomo was meant to be a symbol of Siena’s wealth, power, and divine connection—especially in contrast to its rival, Florence. The architecture is pure Gothic drama: soaring vaults, striped columns, and a façade that looks like it’s been bedazzled by angels. Even from the outside, it’s breathtaking. But inside? It’s a sensory overload in the best possible way.

Everywhere you turn, there’s artwork. The ceilings are painted blue with golden stars. The pillars and arches stretch upward like an army of zebra-striped giants. Statues by Michelangelo. Sculptures by Bernini. Paintings, carvings, mosaics—it’s endless.

But the floor? That’s where it gets truly wild. The entire cathedral floor is made up of more than 50 intricate marble panels—each one telling a story from the Bible or Roman history.

They’re inlaid like puzzles, created by over 40 artists across 200 years. It’s like walking on a sacred graphic novel in stone. The marble panels alone would make this one of the best things to do in Siena.

And then there’s the Piccolomini Library—an explosion of color tucked into the left nave of the cathedral. Commissioned in the late 1400s by Cardinal Francesco Piccolomini (who later became Pope Pius III), this room houses stunning Renaissance frescoes by Pinturicchio and his workshop—some say the young Raphael even helped paint them. The walls are a vivid celebration of classical learning, papal power, and artistic ambition. The ceiling alone is worth the ticket price.

🎟️ Ticket tip: Get the OPA Si Pass, which includes access to the Duomo, Piccolomini Library, Baptistery, Crypt, Museo dell’Opera, and the Facciatone viewpoint. It’s a decent value and covers all the major cathedral sites. Pre-booking is highly recommended, especially if you’re visiting during summer or on a weekend—the line to buy tickets at the entrance can get long and slow in the heat. Booking online saves you from one of the worst things to do in Siena – getting sweaty while waiting outside in the sun in the ticket line.

📸 Italy vibes: If you’re into Italy photography or hunting down rich interior shots for your feed, this is your moment. Try shooting low to capture both the floor and ceiling in one frame—Siena Italy aesthetic unlocked.

✨ Spritzience verdict: I highly recommend going in. Even if you’re a seasoned church-goer (or intentionally skipping churches), this one is in a league of its own. It’s where art, architecture, and devotion meet in the most mesmerizing way.

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5. Climb The Facciatone & Visit The Museo dell’Opera

If you’re short on time and trying to prioritize the best things to do in Siena Italy, here’s a solid shortcut: head straight to the Facciatone.

The Museo dell’Opera del Duomo—right next to the cathedral—is often overlooked, but it’s home to some of Siena’s most important artistic treasures, including Duccio’s Maestà and original statues from the Duomo façade. Still, the real gem here is the climb to the Facciatone: the unfinished wall of what was meant to be the “new cathedral” before the Black Plague halted construction. Today, it’s one of the most unforgettable things to do in Siena Italy.

The visit begins inside the museum, where you’ll wind through a few exhibit rooms and head to the 2nd floor, before emerging into a museum room that functions as a waiting room. Small groups exit and walk across a narrow stone walkway outside and then up a circular stairway. This first set of steps brings you to the lower terrace level, already high above the rooftops with beautiful views of the city and surrounding hills. You can stop here, catch your breath, and soak it in—or continue onward.

From the first platform, a tight outdoor passageway—wide enough for only one person at a time—leads to the final climb up to the second, higher level of the Facciatone. This upper viewpoint is where Siena stuns: you’re face-to-face with the striped dome of the Siena Cathedral, peeking out over tiled rooftops and rolling Tuscan countryside in every direction.

Because the stairs and passages are so narrow, only small groups are allowed up at a time. Even though I visited in shoulder season, there was a queue, and I had to wait—but honestly, it’s absolutely worth it. It felt like a secret rooftop hideaway, a high perch carved out just for those in the know.

🎟️ Spritzience tip: Access is included with the OPA Si Pass, which covers all the major Duomo sites. If you’re visiting during summer or on a weekend, go early—lines form quickly inside the museum. And you know how we at Spritzience feel about waiting in lines, they’re the worst things to do in Siena.

📸 Italy photography moment: This is where you capture the Siena cityscape with cathedral and that quintessential Italy aesthetic—golden light, red rooftops, and the kind of views you’ll want to print, frame, and stare at during winter.

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6. Descend Into The Baptistery And Crypt

Tucked just behind the Siena Cathedral, the Baptistery of San Giovanni and the Crypt offer two very different ways to go deeper—literally—into the city’s religious and artistic legacy. They’re both part of the OPA Si Pass, and depending on your schedule (and your patience for church interiors), they may or may not be top priorities on your personal list of things to do in Siena.

The Baptistery, located at the base of the Duomo’s back steps, is the more striking of the two in my opinion. You walk into a dimly lit space that suddenly opens into a vault of color and sculpture—every surface is decorated with rich frescoes, a vaulted ceiling covered in gold and blue, and a magnificent bronze baptismal font with panels by Donatello, Ghiberti, and Jacopo della Quercia.

It’s intimate but dramatic, with a very different vibe from the grandeur of the main cathedral. If you’re short on time or faced with a queue and need to choose, I’d recommend the Baptistery over the Crypt—it felt more emotionally impactful. And admiring the artisananship of the sculptures on the font, is one of the more interesting things arty things to do in Siena.

The Crypt, accessed around the side of the Duomo, is less decorative and more archaeological in nature. Discovered only in 1999 after being hidden for centuries, it’s raw and atmospheric, with fragments of frescoes dating back to the 13th century. There’s something humbling about walking beneath the Duomo, seeing the layers of history in chipped paint and rough stone. That said, it’s more about mood than masterpieces.

💡 Honest Spritzience take: If the Baptistery and Crypt hadn’t been included in the OPA Si Pass, I likely would have skipped them. The Siena Cathedral itself is so spectacular—so full of artwork, architecture, and sensory overload—that I didn’t feel a deep need to take in more religious imagery afterward. But since they were part of the ticket, I went—and I’m glad I did. Just know your energy levels and time constraints.

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7. Get Inspired at Santa Maria della Scala

If you’re building your list of things to do in Siena, this one’s a must—especially if you’re the type who loves being surprised by a place that feels way bigger on the inside than it looks from the outside.

Santa Maria della Scala sits directly across from the Duomo, and for centuries, it was one of the oldest and most important hospitals in Europe, caring for the sick, poor, pilgrims, and abandoned children. Founded in the 9th century and expanded significantly in the 13th and 14th, it was operated by religious brotherhoods and backed by the city’s wealthy merchant families.

But this wasn’t just a place of medicine—it was also a center for charity, worship, and art. Today, it’s been transformed into a multi-level museum complex, and to me, it was one of the most unexpected gems in Siena Italy.

There were three standout experiences that made this site feel essential:

1. The Room of Frescoes
One of the first rooms I walked into literally stopped me in my tracks—walls entirely covered in frescos that told the story of the hospital’s early days. The artwork was vibrant and cinematic, but what I really loved was how each fresco had a detailed description in both Italian and English below it. It felt like walking through a visual novel, with characters and plot twists right there in paint. It brought the space—and its centuries of service—beautifully to life.

2. The Treasure Room
Tucked deeper into the museum is a dimly lit chamber filled with relics, precious jewels, and medieval treasures that transported me straight into the mindset of a 14th-century pilgrim.

One item that really stood out: a bible cover donated by a merchant who had purchased it in Constantinople in 1359. I stood there imagining the journey it took to get here—and how Siena’s global connections reached far beyond Tuscany.

3.Step Inside the Hidden Chapels of Siena’s Healing Monks and Nuns

Before the museum era, before the tourists and ticket booths, Santa Maria della Scala was a place of service—and spirituality. As one of the oldest hospitals in Europe, it was run for centuries by religious orders of monks and nuns who lived and worked on site. Quietly tucked into side corridors and stairwells, you’ll still find the chapels they used for daily prayer, tucked like sacred secrets beneath the grandeur of the Duomo.

These hidden chapels were among my favorite surprises inside the Santa Maria complex. One was small and cave-like, dimly lit with simple wooden benches and a plaques naming the brothers and sisters whom had led charitable works there. Another had faded frescoes of saints and healers watching over the space, as if the walls themselves still remembered the people who came here seeking hope—or peace. You won’t find these listed at the top of guidebooks or marked with big signs, but if you explore slowly and pay attention to the side passages, you’ll stumble upon them.

It’s a moving reminder that Siena’s artistic beauty was born not just of wealth and politics, but also of care, compassion, and quiet devotion. These chapels made me pause and breathe a little deeper.

8. Visit The 2 Underground Museums at Santa Maria Della Scala

What completely blew me away was what’s underneath. At the basement level, you’ll find both the Archaeological Museum and the Medieval City Museum, all built into what feels like a labyrinth of stone caverns and vaulted corridors. It was honestly the most atmospheric museum setting I’ve ever experienced—it felt like exploring a cross between underground catacombs and an Indiana Jones set. I was wandering among Etruscan sarcophagi and medieval hallways wondering, How is this not more famous?

✨ Bonus: It’s deliciously cool inside, providing yet another reason why it’s one of the best things to do in Siena. On a summer day, Santa Maria della Scala is an absolute sanctuary from the heat. As someone who’s lived in Milan for ten years, let me remind you: air conditioning in Italy is not what most Americans are used to. Even places that advertise A/C are usually lightly cooled. But this museum? Natural climate control courtesy of ancient stone walls—and it felt like heaven.

🎟️ Spritzience tip: Entry is separate from the OPA Si Pass, but it’s worth every cent. Plan for at least 1.5–2 hours if you want to explore without rushing.

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9. Step Into Siena’s Contrada Culture at a Neighborhood Museum

If you really want to understand the heartbeat of Siena, don’t just marvel at the architecture—get to know the contrade. These aren’t just districts or neighborhoods; they’re identities passed down through generations, each with its own flag, mascot, church, museum, and centuries of Palio pride. Think Hogwarts Houses—but with medieval armor, marching bands, and horses trained for glory.

There are 17 contrade in total, and during Palio season (July 2 and August 16), the city erupts in colorful pageantry and fierce, joyful rivalry. But even outside those dates, you can experience contrada life by visiting one of their museums, which are small, community-run spaces filled with flags, artifacts, and reverence.

During my visit in June while chasing the Mille Miglia, I stopped by the Museo della Contrada del Leocorno—the Unicorn Contrada—and it was one of the most genuine cultural experiences I had in Siena. The museum is just a short walk from Piazza del Campo, tucked inside quiet lanes that feel a world away from the crowds. Leocorno is known for its spirited pride and deep historical roots, and its museum reflects that beautifully: a room lined with old Palio banners, hand-painted drums, and sacred relics tied to the contrada’s patron saint.

✨ Why I recommend Leocorno:
It’s conveniently located near the Campo, often less crowded than other museums, and the volunteers are incredibly welcoming—even if you don’t speak fluent Italian, they’ll walk you through their proud history with enthusiasm. It’s one of the most unique things to do in Siena.

🕘 Opening hours:

• May through September
• Monday to Saturday: 17:00–19:30
• Friday & Saturday mornings: 10:00–12:30
• (Double-check local signage when you’re there, as hours may occasionally shift with events.)

🔔 Spritzience tip: These museums are rarely listed in major guidebooks but are a brilliant way to step off the tourist track and see what keeps Siena’s soul alive. Visiting one made me appreciate just how deeply these traditions are embedded into daily life—even the baker, the bartender, and the banker are probably cheering for different horses!

10. Tasty things to do in Siena – Savor Siena’s Signature Sweets: Ricciarelli & Panforte

If you’ve been walking all day, climbing towers, exploring crypts, or chasing Mille Miglia cars like I was, it’s time to reward yourself the Siena way: with something sweet, delicate, and historic. Trying Siena’s traditional pastries isn’t just a snack break—it’s one of the tastiest things to do in Siena Italy, especially if you’re into culinary history as much as flavor.

Two absolute must-tries? Ricciarelli and Panforte. These aren’t just desserts—they’re centuries-old edible souvenirs that reflect Siena’s medieval soul.

🍪 Ricciarelli

Soft, chewy, and delicately powdered with sugar, ricciarelli are almond-based cookies that look like little pillows of bliss. They’re made with almond flour, egg whites, sugar, and orange zest—resulting in a texture that’s somewhere between marzipan and a cloud. Originally created in the 14th century, they were a luxury item enjoyed by nobility and gifted during Christmas, though thankfully today they’re available year-round.

🍫 Panforte

Now for something richer. Panforte is a dense, spiced fruitcake loaded with honey, nuts, candied citrus peel, cinnamon, cloves, and sometimes a hint of black pepper. Legend has it that it was created by apothecaries and monks as an energy-rich delicacy, especially for pilgrims passing through Siena on their way to Rome. The name means “strong bread,” and it is intense—chewy, sticky, sweet, and savory all at once. It pairs beautifully with a tiny espresso or a glass of Vin Santo if you’re feeling indulgent.

Fun fact: the oldest surviving recipe dates back to 1205. If that doesn’t count as one of the most historic things to do in Siena, I don’t know what does.

☕ Where To Try Them

I highly recommend stopping at Nannini on Via Banchi di Sopra—a historic pasticceria that’s been baking up these treats for generations. Grab a few ricciarelli to go or sit down with a slice of panforte and a macchiato. Another great option is Pasticceria Sinatti, especially if you’re meandering around the quieter Siena Italy streets just beyond the Campo.

✨ Spritzience tip: Many shops sell beautifully wrapped boxes of ricciarelli and panforte, perfect to bring home as gifts (or just for yourself when the post-vacation blues hit). They travel well and make your suitcase smell faintly like Siena—no complaints there.

📸 Italy aesthetic bonus: Panforte displays in shop windows are often works of art themselves—neatly stacked, tied with ribbons, and presented like edible antiques.

11. Sip Tuscan Wine With a View at Enoteca I Terzi—Or Go Underground at Sotto al Duomo, or Boutique at Treflari

After a full day of fresco gazing, tower climbing, and museum wandering, few things to do in Siena feel more deserved—or more decadent—than a wine break. Sampling local vintages is one of the most relaxing and indulgent things to do in Siena, and luckily, this city knows how to treat a wine lover right. Whether you’re in the mood for a scenic glass, a sommelier-led tasting, or a chic boutique experience, Siena delivers.

🍷 Enoteca I Terzi – Relaxed & Scenic

Let’s start with my personal favorite for golden hour: Enoteca I Terzi, perched along a peaceful stretch of Siena Italy streets near the Duomo. The vibe is effortlessly elegant without being fussy, and the wine list focuses on local Tuscan varietals—Chianti Classico, Brunello di Montalcino, and Vino Nobile di Montepulciano among them.

I opted for a three-glass tasting flight and a tagliere (Tuscan charcuterie board), and suddenly, my feet didn’t hurt so much, the sun was glowing just right, and life felt very, very Italian.

🕯️ Enoteca Sotto al Duomo – Atmospheric & Expert-Led

Looking for something more immersive? Head just a few steps from the cathedral to Enoteca Sotto al Duomo, a wine lover’s sanctuary hidden inside a vaulted medieval cellar. The vibe here is intimate and refined, with guided tastings led by knowledgeable sommeliers, making for one of the most refreshing things to do in Siena.

They offer everything from bold Super Tuscans to off-the-radar small producers—and they’re happy to tailor flights to your taste. The arched brick ceilings, soft lighting, and reverent hush make it feel like you’ve stumbled into a wine chapel. It’s a perfect choice for small groups or anyone who wants to go deeper into the world of Tuscany Italy wines.

🥂 Treflari – Boutique, Stylish & Sophisticated

If you’re in the mood for something modern and stylish, Treflari offers a fresh twist on the Siena wine experience. This sleek, design-forward tasting room brings a boutique sensibility to the local wine scene. Here, it’s not just about sipping—it’s about story.

Staff are passionate about what they pour and love sharing insights on lesser-known Tuscan winemakers. I loved the attention to detail, the contemporary ambiance, and the sense that this was a place locals actually go. It’s a great stop for aperitivo with an edge—or a smart pairing experience before dinner.

12. Peek Inside Palazzo Salimbeni—Banking Royalty Since the 1400s

Siena may look like a sleepy medieval town from above, but don’t let the terracotta calm fool you—it was once a powerful financial force in Europe. Nowhere is that legacy more evident than at Palazzo Salimbeni, a Gothic stone building that quietly exudes centuries of wealth and influence. Tucked into Piazza Salimbeni, just a few minutes’ stroll from the Campo, this stately palace is the headquarters of Banca Monte dei Paschi di Siena, the oldest surviving bank in the world, founded in 1472.

Yep—that old. That’s over 500 years of continuous operation, making it one of the most enduring institutions in financial history. For anyone interested in the Siena Italy background, this site adds a totally different layer to the city’s story—one of civic power, not just cathedrals and contrade.

The building itself is impressive from the outside, with a Neo-Gothic façade that was redesigned in the 19th century but still fits beautifully into the surrounding medieval architecture. Its pointed arches, battlement-style cornices, and striking stonework feel like a subtle nod to Siena’s once-fierce independence. At the center of the square stands a statue of Sallustio Bandini, an 18th-century Sienese priest, economist, and early free-market thinker. It’s a beautiful, quiet piazza that feels unexpectedly grand—and oddly serene, especially early in the morning or just before sunset.

While you can’t freely roam inside the bank (this is still a working financial institution, after all), the courtyard is often open, and it’s worth slipping into the entry to admire the vaulted ceilings and decorative details. Occasionally, the bank opens its halls for special exhibitions or cultural events—so if you see one advertised during your trip, jump at the chance. It’s an atmospheric slice of Siena Italy streets that most tourists walk right past.

✨ Why it belongs on your list of things to do in Siena Italy:
Because it tells a lesser-known chapter of Siena’s story—its role as a banking powerhouse and innovator long before Wall Street was even a dream. And because sometimes, a beautiful piazza with a great statue and an even better backstory is all you need for a perfect midday pause.

🕰️ Spritzience tip: Swing by en route to aperitivo or while shopping nearby on Via Banchi di Sopra—it’s an easy, enriching stop that doesn’t take long but leaves an impression.

13. Visit the Università di Siena – One of Europe’s Oldest Universities

While most people come to Siena for cathedrals and cobblestones, there’s a more dynamic side of the city hiding in plain sight—its university. The Università di Siena, founded in 1240, is one of the oldest continuously operating universities in Europe and has long been a center of intellectual life in Tuscany Italy. With a student body of around 15,000, the university brings youthful energy and a sense of curiosity that balances out the city’s medieval seriousness.

Walking through the university area, you’ll notice a very different vibe than around the Campo—more cafes filled with laptop-tapping students, poster-covered walls advertising debates and concerts, and an undeniable sense of local pride. I wandered through the main university buildings, tucked between Via Banchi di Sotto and Via di Città, and loved how seamlessly they blended into the city’s stone fabric. No sprawling modern campus here—just ivy-covered courtyards, Renaissance staircases, and lecture halls that look like they’ve hosted centuries of brilliant minds.

✨ Why it made my list of top things to do in Siena Italy:
Because it adds depth to the city’s story. While Siena is known for its religious and artistic legacy, this place reminds you it’s also been a hub of medicine, law, and humanism since the Middle Ages. It’s a living, breathing institution—not a museum—and it adds texture to the Siena Italy background in a way that feels very real.

Some of the historic university buildings (like the Rettorato) are open to visitors during exhibitions or student-led events, so if you’re visiting in spring or fall, peek at what’s going on—you might stumble into a public lecture, courtyard concert, or student art show.

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14. Watch the Sunset from Fortezza Medicea—Then Stay for a Summer Concert

If you’re looking for a peaceful spot to unwind at golden hour, the Fortezza Medicea (also known as Forte di Santa Barbara) is one of the most underrated things to do in Siena. Located just outside the historic center’s northern gate, this 16th-century fortress was originally built by Cosimo I de’ Medici to keep the rebellious Sienese in check after Florence took control of the city. Today, the only battles happening here are between locals over who brought the better bottle of Chianti.

The fortress is free to enter and open to the public, with tree-lined walking paths, sweeping views over the Tuscan countryside, and a wonderfully relaxed vibe. Locals jog here in the morning, walk dogs at sunset, and stretch out on the old brick walls with books and Aperol spritzes. The views at dusk are incredible—you can see Siena’s cathedral dome rising above the rooftops, vineyards in the distance, and the whole city bathed in that signature Tuscany Italy glow.

But here’s the secret sauce: in summer, the Fortezza transforms into a full-on cultural hub. You might stumble into a jazz concert, a theater performance, or even an open-air wine festival. During my visit in June, I wandered in expecting a quiet stroll and ended up catching a local band playing under the stars with a wine glass in hand. Total serendipity.

🎭 Want to plan ahead?
Stop by the Siena Tourist Office and ask for a printed guide called “Che C’è in Fortezza” (“What’s On at the Fortress”). It lists all the events happening at the fortress by date and time, including concerts, food festivals, film screenings, art exhibitions, and community events. Most are free or low-cost, and it’s one of the best ways to experience Siena like a local.

📸 Italy photography tip: Head to the fortress wall that faces the city center for the best panoramic shot of the Siena cityscape with cathedral. The light is especially dreamy between 7:30–8:30 PM in summer.

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15. Catch the Mille Miglia Roar Through Siena’s Historic Streets

There’s exciting—and then there’s Mille Miglia in Siena exciting. I actually planned my trip to Siena specifically to coincide with this legendary race, and let me tell you: it was one of the amazing things to do in Siena. Few experiences have ever blended speed, beauty, and history quite like this. It felt like stepping into a vintage Italian film—except I was right there, pressed against a medieval stone wall as roaring Ferraris flew past my ankles.

The Mille Miglia (literally “1,000 miles”) is one of the most iconic motor races in the world. Originally launched in 1927 as a road race from Brescia to Rome and back, it was reimagined in 1987 as a glamorous vintage car rally, featuring meticulously restored pre-1957 race cars. Each summer in mid-June, these beauties roll through some of Italy’s most stunning towns—including Siena, where they make a checkpoint stop for lunch.

And Siena doesn’t just host the Mille Miglia—it throws a full-blown style moment. In Piazza del Campo, organizers unfurl long red, white, and green carpets to mimic the Italian flag, transforming the already cinematic square into a vibrant, high-octane display of national pride and vintage elegance.

As the cars roll into the square and line up on the tricolor runway, you’re able to walk right up to them, chat with the drivers, and admire the curves of a classic Bugatti, Alfa Romeo, or Jaguar framed by Gothic palaces and medieval bricks.

✨ It was absolutely magical. I visited the tourist office with a map, and they were able to draw the Siena portion of the route in. From there, I strategically positioned myself along a narrow side street just before the Campo to watch the cars zoom in from the countryside. They come fast. Really fast. And since Siena’s historic streets weren’t exactly built for 20th-century speed machines, let’s just say… there’s not a lot of room for error.

I had to keep reminding myself to press back against the wall—because honestly, I was so close I could’ve lost a toe to a vintage Maserati. The smell of gasoline, the squeal of tires echoing between the stone buildings, the crowd cheering—it was total sensory overload in the best way possible. The drivers are excited to be there, they’re filming the crowd and the crowd is filming the drivers – the spirit of the race is catchy.

🎬 Movie moment alert: If you’ve seen the recent “Ferrari” (2023) film starring Adam Driver, the Mille Miglia plays a key role. The film dramatizes the emotional and professional stakes of Enzo Ferrari’s life, particularly surrounding the 1957 Mille Miglia, making this real-life race feel all the more epic and poignant when you see it up close.

🗓️ When to catch it: The Mille Miglia typically takes place over four days in mid-June. Siena is often a midday checkpoint stop—perfect for lunch and admiring the cars at rest before they race off again. Check the official Mille Miglia website for the most current route as it changes a bit every year. Or read this Spritzience post for more information on how to chase the Mille Miglia and plan your ultimate road trip.

🏁 Spritzience tip: Even if you don’t know your Ferraris from your Fiats, this event is a thrill. It’s one of the few moments in life where you can sip a spritz in a medieval piazza while classic cars race past on cue.

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16. Pay Homage to Saint Catherine of Siena—Italy’s Fierce and Fearless Patron Saint

If you’ve spent any time wandering the streets of Siena, you’ve likely heard about Saint Catherine—and for good reason. She’s not just a hometown hero, she’s a patron saint of Italy, a Doctor of the Church, and a deeply influential mystic, writer, and political negotiator whose legacy reaches far beyond the quiet stone lanes of her birthplace. Visiting her sanctuary is one of the most meaningful—and moving—things to do in Siena Italy.

Located just outside Porta Romana, in a peaceful part of the city that sees fewer tourists, the Sanctuary of Saint Catherine (Santuario di Santa Caterina) is built on the site of her childhood home. The complex includes her original family home, a small 15th-century cloister, and two richly decorated chapels: Cappella della Cucina and Cappella del Crocifisso.

The entire space feels humble yet sacred. You’ll walk through passageways and quiet stone rooms that once housed a young Catherine—who, by the age of seven, had already devoted herself to a spiritual life. She later became a powerful voice in European politics, helping negotiate peace between warring Italian states and even persuading the Pope to return the papacy to Rome from Avignon. Not bad for a woman from medieval Siena Italy streets, right?

Inside the sanctuary, you’ll find:

• Original frescoes depicting scenes from her life
• The room where she cared for the sick during times of plague
• A small museum with personal items and relics

🕯️ Spritzience moment: Whether you’re religious or not, there’s a quiet power to this space. As someone who’s lived in Italy for ten years and visited many, many churches, this one struck a different chord—intimate, grounded, and filled with a sense of real humanity. Catherine wasn’t born into wealth or fame. She was a dyer’s daughter who used her voice—and pen—to change the course of history.

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Where to Stay in Siena (If You’re Staying—and You Should!)

Let’s be honest: Siena can technically be done as a day trip. But after chasing Mille Miglia cars through ancient alleyways, sipping Brunello on hidden terraces, and watching golden light wash over striped cathedral domes, I’d strongly argue that Siena deserves a night or two—especially if you want to enjoy the city once the day-trippers vanish and the streets settle into that peaceful Tuscan hush.

Here are two standout stays for different moods and budgets—both centrally located, both rich in character, and both ideal for adding that “this is my life now” feeling to your Italy trip planning.

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Grand Hotel Continental – For the Full Tuscan Nobility Fantasy

If you’re in the mood to feel like Italian royalty, this is your place. The Grand Hotel Continental is a 5-star stunner located just off Via Banchi di Sopra, one of the main pedestrian shopping streets in Siena Italy. Housed in a 17th-century palazzo, it’s filled with frescoed ceilings, marble floors, and sparkling chandeliers—but without the stiffness you sometimes get in ultra-fancy hotels.

Rooms are elegant and airy, with views over Siena’s rooftops and rolling hills. There’s an on-site wine cellar carved into the rock, and the staff genuinely go out of their way to make you feel pampered without being precious. It’s perfect for a romantic getaway, a milestone birthday, or just a “treat yourself because life is short” moment. This is affordable luxury at its best!

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Il Giardino di Pantaneto – For Boutique Charm & Garden Views

If you want something more intimate and local—but still stylish—Il Giardino di Pantaneto is a hidden gem. This boutique guesthouse is tucked into the southern edge of the historic center, close to Porta Romana and a scenic walk from the main sights. What makes it special is right there in the name: the garden.

It’s rare to find green space inside Siena’s walls, and this place delivers a lovely one—with tables, lounge chairs, lemon trees, and views across the countryside. Inside, the rooms are cozy and full of personality, with thoughtful design touches and a warm welcome. It feels more like staying at a (very cool) friend’s Tuscan villa than a hotel.

✨ Spritzience tip: If you can, spend at least one night in Siena, it lets you enjoy the things to do in Siena at a more relaxed pace. You’ll also experience a completely different feel of the city once the crowds disappear and the city belongs to the locals again. Walk the empty Campo under the stars, enjoy a late dinner, and start your next morning with a slow cappuccino while the bells ring out across the rooftops.

How to Get to Siena

Traveling to Siena Italy by train is straightforward and scenic—perfect for adding that Tuscany travel ambiance to your Italy trip planning. Here’s a breakdown of the best routes from Milan, Florence, and Rome, including durations, ticket tips, and starting points of interest. And for any of the high-speed freccia trains, it’s always a great idea to book in advance, as you can usually save money by doing so.

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🚆 From Milan to Siena

• Average travel time: ~4.5 to 5 hours, with at least one transfer, typically in Florence or Bologna
• Fastest routes (with high-speed Frecciarossa to Florence, then regional train to Siena): around 4 h 30 m
• Typical fare: from €60 when booked in advance .
• Departure: Milano Centrale; arrival at Siena station—about a 10–15 min mild uphill walk to the city center (or quick bus ride).

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🚄 From Florence to Siena

• Travel time: Typically 1.5 hours to 1.45 hours on regional trains
• Frequency: Around 15 trains daily, departing from Florence SMN, with most requiring a change in Empoli
• Fare: From €10
• Arrival: Siena station, then uphill walk or bus to the heart of the city.

Alternate option: Buses (FlixBus or AT Bus) drop you closer to the Campo—handy for day-trippers .

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🚅 From Rome to Siena

• Travel time: About 3.5 hours, usually with one change (via Florence or Chiusi)
• Frequency: Around 9–15 trains per day
• Fare: From €35 when booked in advance; allow extra time for changes.

Siena As Part of A Tuscan Itinerary

Siena is more than just a postcard-perfect hill town—it’s a living, breathing piece of Tuscan history, layered with beauty, tradition, and those little magical moments that stay with you long after you’ve left. Whether you’re here for one day in Siena or staying overnight to soak in the full Siena Italy aesthetic, the city delivers with an irresistible blend of culture, cuisine, and charisma.

And if you’re building out a full Tuscany itinerary, Siena fits in seamlessly alongside gems like Pienza and its amazing restaurants, the rolling landscapes of the Val d’Orcia, and the medieval towers of San Gimignano. It’s a perfect base—or highlight—for anyone chasing those dreamy Italy vibes across Toscana Italia.