17 Incredible Things to Do in Siena, Italy + Helpful Tips
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If you’re traveling through Tuscany and skip Siena, you’re seriously missing out. From visiting the magnificent Duomo di Siena to wandering the Piazza del Campo, there are so many incredible things to do in Siena.
I’ve visited Siena many times, and each trip makes me love it more. It’s a little moodier and more grounded than Florence – with its warm brick buildings, colorful neighborhood flags, curved cobblestone streets, and stubborn sense of pride.
Historically, Siena was Florence’s great rival – a powerful medieval banking city with its own wealth, cultural identity, and fiercely loyal neighborhoods shaped by the Palio. Even though only 60 minutes separate these Tuscan cities, that rivalry is as real as ever. Just ask any local.
If you’re short on time, you can see Siena’s highlights in a few hours – and that’s why it’s one of the most popular day trips from Florence. (I’ve day-tripped to Siena a few times, by rental car and on this epic Tuscany in One Day trip.) Just know that mid-day in Siena is crowd-o’clock.
Mornings and evenings are a different story, though. Once the day-trippers clear out, Siena exhales. Cafés slow down. Locals linger. And the streets feel lived-in again, in a way Florence’s Centro Storico doesn’t anymore. So if you plan to explore more of Tuscany, Siena is an excellent home base.
Whether you’re planning a day trip to Siena from Florence or staying for a few days (good idea!), this guide covers all the best things to do in Siena – including what to eat, where to drink, and the can’t-miss experiences worth booking ahead.
Quick Picks: Plan Your Siena Trip
Best Things to Do in Siena:
- Go on a guided walking tour of Siena with skip-the-line Duomo access
- Visit the Piazza del Campo (and learn about the Palio)
- Tour the Duomo di Siena and the Duomo complex
- Climb the Torre del Mangia for panoramic views
- Walk along the Medici Fortress for a scenic break
Best Food & Wine Experiences in Siena:
- Take a Tuscan cooking class in Siena’s historic center
- Join a walking food tour to try authentic Sienese specialties
- Go wine tasting at an organic vineyard just outside Siena
Best Day Trips from Siena:
- Explore Val d'Orcia wineries, farms, and medieval villages (Montepulciano, Pienza, Montalcino)
- Visit Chianti wineries and San Gimignano
- Hike the ancient Via Francigena trail to Monteriggioni
1. Take a Guided Walking Tour of Siena
If it’s your first time visiting Siena, taking a historical walking tour of Siena is essential.
As you walk through Siena’s charming streets, you’ll notice centuries-old brick buildings, brightly colored shutters, marble statues tucked into corners, and colorful neighborhood flags marked with quirky symbols like dolphins, caterpillars, unicorns, she-wolves, and dragons.
But without a local guide (who will ooze passionate Sienese pride, no doubt), you won’t know why any of it matters.
The traditions and history of Siena are what make the city so special – from the Palio di Siena (the biannual horse race) and the contrade (neighborhood) system, to Siena’s powerful banking past, its famous panforte (fruitcake), and the long-standing rivalry with Florence.
A guided walking tour will connect all of these threads in a way that wandering on your own can’t.
Best Guided Walking Tours of Siena
- Visiting Siena on your own? I recommend this Siena City and Duomo Guided Walking Tour. I booked it on my most recent visit and loved it. We visited the Duomo, the Piazza del Campo, and lesser-visited gems (like the Basilica Cateriniana San Domenico), explored quiet neighborhoods, learned about Siena’s culture – from horse-blessing ceremonies to the meanings behind the contrade symbols. Book your Siena City and Duomo Guided Walking Tour here.
- Taking a guided day trip to Siena? Choose one that already includes a guided walking tour of the historic center and the Duomo, plus free time to explore on your own. (I highly recommend this Tuscany Highlights Day Trip from Florence – I’ve done twice!)
2. Wander the Piazza del Campo
The Piazza del Campo is the city’s sloped, clam-shaped main “square.” As the heart of Siena’s historic center, and the locals’ collective living room, it’s a place you can’t miss.
The piazza is framed by the Gothic-style Palazzo Pubblico and the soaring Torre del Mangia, along with the marble Fonte Gaia, historic brick buildings, and a ring of cafés and wine bars. Some call it one of Italy’s most beautiful piazzas, and I tend to agree!
But Piazza del Campo isn’t just scenic. Twice a year, it transforms into the racecourse for the Palio di Siena.
About the Palio di Siena (in Piazza del Campo)
You can’t really understand Siena without understanding the Palio, the contrade (neighborhoods), and the rivalries between them. Palio isn’t just a quirky historic tradition – it’s part of daily life for the Sienese.
Every year, on July 2 and August 16, Piazza del Campo hosts the Palio di Siena, a bareback horse race that dates back to the 13th century.
In racing season, the entire city shifts into Palio mode. Homes are decorated, communal dinners are held, and horses are blessed inside each contrada’s church. Processions and music fill the streets, while packed sand covers the cobblestones to form a racecourse.
And on race days, tens of thousands of spectators pack into Piazza del Campo to watch colorfully costumed jockeys race around the square.
If you want to attend the Palio, plan far in advance. You can purchase balcony tickets to watch the race (very pricey), or join the festive chaos in the center of the piazza for free.
3. Eat Your Way Through Siena
Discovering Sienese cuisine is one of the best things to do in Siena! The food here is deeply traditional, proudly regional, and closely tied to the surrounding countryside. And most importantly, it’s so, so delicious.
You won’t find many trendy menus here. Instead, rustic nonna-style food (like handmade pasta and slow-simmered sauces) and a few iconic local specialities are the stars of the show…
The most famous is panforte di Siena, a dense, spiced fruit-and-nut cake that dates back to the 13th century. You’ll see it everywhere as you wander the streets of Siena. Try it with your morning espresso or a glass of dessert wine!
Other Sienese and Tuscan classics to seek out include hand-rolled pici pasta (basically, fat spaghetti – my absolute favorite!), ribollita (bread soup), wild boar ragù, slow-simmered fagioli (white beans), pappardelle pasta (flat, wide noodles), and seasonal truffle-covered dishes.
You’ll also find ciaccino bread sandwiches filled with local meats (made from wild boar or the prized native Cinta Senese pork) and pecorino cheeses.
Best Siena Foodie Experiences
If you want to go beyond ordering from a menu, these two foodie experiences are worth booking:
- Tuscan Cooking Class in Central Siena: In this hands-on cooking class, you’ll learn how to make five traditional Tuscan recipes from scratch. With local wine within arm’s reach, you’ll make authentic dishes like pappa al pomodoro (tomato and bread soup), hand-rolled pici pasta with aglione sauce. This class starts at 4 PM, so it’s easy to fit into a day trip and doubles as dinner! Book your Tuscan cooking class in Siena here.
- Siena’s Ultimate Food Tour: This guided foodie walk will take you to a variety of artisan food shops, market stalls, and local eateries in Siena’s historic center. You’ll try local meats, cheeses, handmade pasta, sweets, and so much more – all while learning about Siena’s food culture and history. Book your Siena walking food tour here.
Where to Eat in Siena
Here are some of my favorite places to try traditional Sienese and Tuscan food in the Centro Storico.
- Il Bocconcino: My favorite sandwich shop near the Piazza del Campo! Friendly service and delicious panini with high-quality local meats and cheeses. Perfect for a quick, delicious lunch if you’re short on time!
- Bakery Il Magnifico: A great spot for authentic Sienese sweets, including the iconic panforte di Siena (fruitcake) and fragrant cavallucci cookies (made with nuts, honey, citrus, and spices)
- Osteria Il Carroccio: If you only have time for one osteria, make it this one! And make a reservation. It’s popular for Sienese and Tuscan classics like lampredotto, pici al ragù senese, and fresh-truffle-topped steak. For dessert, order the ricciarelli (chewy almond cookies).
- Osteria Permalico: A cozy spot for an afternoon aperitivo or traditional Tuscan dishes and wine. I love sitting outside on the sloping street and people-watching.
- La Taverna di San Giuseppe: A standout for classic and modern Tuscan dishes like homemade pappardelle with beef ragù and risotto with Chianti wine and local sausage, served in a beautiful brick space. There’s even an ancient Etruscan wine cellar!
- Osteria Nonna Gina: A family-feeling restaurant in a quieter part of town known for their pasta dishes. Order the gnocchi alla Lella.
- Pizzeria Alle Scalette: Pizza isn’t from Siena… but if you’re in the mood for it, this is a solid Neapolitan-style option.
MADDY’S TIP: Interested in regional Italian food culture? I know I am! Siena pairs beautifully with three days in Florence (think: wine windows, trattorias, gelaterias, and Florentine steaks), and a trip to discover the best foodie things to do in Bologna – including visiting Bologna’s food factories.
4. Drink Local Wine in Siena
Some of Italy’s most celebrated wines come from the province of Siena, so drinking well here is easy! And of course, it’s one of the best things to do in Siena.
Think DOCG reds like Brunello di Montalcino and Vino Nobile di Montepulciano, and Vernaccia di San Gimignano (Italy’s first DOCG white). Plus, there are lots of smaller local producers you can’t find outside of Tuscany.
For casual sipping, Trefilari Wine Bar is my top pick.
Though, for something more structured, this classic Tuscan wine-tasting class in the heart of Siena is a great option. You’ll taste several regional wines and actually learn what makes them special – without having to drive anywhere! Book your Siena wine-tasting class here.
Want to drink local Sienese wine where it’s made? This 3-hour tasting at a local organic vineyard just outside Siena’s city walls includes a tasting of four different wines, a traditional lunch, and a tour through the vineyards. Transportation isn’t included, but the vineyard is super close – about a 15-minute taxi ride, or a scenic one-hour walk if you’re up for it! Book your Siena vineyard tour and wine tasting here.
5. Visit Siena Cathedral (Duomo di Siena)
Every corner of Siena is beautiful, but the Duomo di Siena (Siena Cathedral) dazzles.
Construction began in the 13th century, and inside and out, the cathedral is a masterpiece of medieval ambition and craftsmanship. Every surface is deliberate and unapologetically extravagant – from the black-and-white marble façade to the richly layered interior.
Major Renaissance and Baroque artists left their marks here, including Pisano, Michelangelo, Bernini, and Donatello. Inside, you’ll find intricately carved marble floors, museum-worthy sculptures, and frescoes that are remarkably well-preserved.
My favorite part of the cathedral, though, is the Piccolomini Library. It’s small but unexpectedly colorful, with floor-to-ceiling frescoes that tell detailed stories, plus ancient manuscripts displayed in pristine condition.
Visiting the Duomo di Siena tops my personal list of the best things to do in Siena. To me, it’s just as impressive as visiting the Vatican or the Basilica of St. Francis in Assisi, Italy.
Maddy’s Tips for Visiting the Siena Cathedral
- Book a guided tour if you can. If you book the Tuscany Highlights Day Trip from Florence or the Siena City and Duomo Guided Walking Tour I recommended earlier, skip-the-line Duomo tickets and a guided visit are already included. This makes a huge difference inside!
- Visiting independently? Get the Opa Si Pass. You can purchase it in person. It includes entry to the Siena Cathedral, plus the rest of the monumental complex. Prices vary by date (typically €14 to €16).
- Dress code is strictly enforced. Shoulders and knees must be covered to enter the cathedral. Ladies, in the summer, I recommend a long, flowy dress or skirt and a lightweight linen shirt or scarf to throw over your shoulders. Don’t assume they’ll let it slide – because they won’t.
6. Explore the Duomo Complex
If you have time after visiting the Duomo itself, exploring the wider Duomo complex will add a bit more depth to your visit. This is where you’ll start to understand just how ambitious Siena’s plans for the cathedral once were…
With the Opa Si Pass, you’ll also have access to the:
- Facciatone: A panoramic viewpoint offering sweeping views over Siena’s rooftops and countryside. It’s part of the unfinished “New Cathedral” project.
- Battistero di San Giovanni Battista: A smaller church with an ornate façade and an impressive interior.
- Museo dell’Opera (Opera della Metropolitana): A small but worthwhile museum housing sculptures, frescoes, and Renaissance art originally created for the cathedral.
- The Crypt (Cripta del Duomo): Rediscovered in 1999, the crypt features vividly preserved frescoes that were hidden for centuries.
7. Climb the Torre del Mangia
Siena’s iconic medieval bell tower, the Torre del Mangia, rises 102 meters (about 335 feet) above Piazza del Campo and dates back to the 14th century.
From the top, the views sweep over Piazza del Campo and Siena’s terracotta rooftops, past the backside of the Duomo, and out toward the old city walls and rolling hills beyond.
There’s only one way up: a very narrow staircase of 400 steps. (No elevator!) Luckily, entry is timed, so visitors can only travel in one direction at a time.
Tickets cost €10 for the tower, or €15 for a combo ticket that includes the Civic Museum inside Palazzo Pubblico.
Open daily. Hours vary by season.
MADDY'S TIP: You have to reserve your 30-minute time slot for the tower, so I recommend stopping by in the morning to snag your tickets – particularly in the busy summer season. I bought the combo ticket and found it worth it for a quick, back-to-back visit.
8. Visit Palazzo Pubblico & the Civic Museum
After you summit the Torre del Mangia, head straight into the Civic Museum, housed in the Gothic 13th-century Palazzo Pubblico (A.K.A. Siena’s town hall).
Inside, you’ll find Siena’s most famous fresco cycle depicting good and bad governance – a surprisingly blunt, almost modern take on how medieval Siena understood power, justice, and civic responsibility. Beyond the frescoes, the museum includes ornate council chambers, grand staircases, ceremonial halls, and period furnishings that bring Siena’s political past to life.
I spent about 30 minutes at the museum. It was interesting, and a worthy and welcome escape from the midday heat.
Open daily. Hours vary by season.
9. Step Inside the Basilica of San Domenico
I first visited the Basilica of San Domenico (also known as the Basilica Cateriniana, after St. Catherine of Siena) during this Siena City and Duomo Guided Walking Tour. And what a hidden gem it is!
Compared to the Duomo, this 13th-century basilica’s architecture and decor are pretty simple. But culturally, it carries enormous weight.
St. Catherine is central to Siena’s identity, and while you’ll hear her full story on your guided walking tour, I’ll spoil one unforgettable detail: inside the basilica, her relics (specifically, her mummified head and a finger) are on display.
MADDY’S TIP: Want to know where I snapped the photo above of Basilica of San Domenico? You’ll find this viewpoint on Via Diacceto. It’s easy to miss but worth seeking out!
10. Take a Break at the Medici Fortress (Fortezza Medicea)
Shoutout to my husband for finding this hidden gem!
Even though the Sienese historically hated the Medici, they love the Medici Fortress (even if it still bears the Medici coat of arms). When museums and cobblestone streets start to feel like too much, this is your chance to slow things down.
Today, the fortress is a calm, leafy park and walking loop just outside the historic center. It’s quiet, off the typical tourist trail, and especially pleasant in the late afternoon or early evening. And since it’s elevated, it offers beautiful views over Siena’s medieval center.
11. Go Truffle-Hunting in the Countryside
One of my all-time favorite experiences near Siena is truffle hunting. My husband and I did this together, and it was such a fun change of pace from churches and museums!
On this Truffle Hunting Experience from Siena, you’ll head into the countryside with a local truffle hunter and his expertly trained (and super cute) dogs and walk through quiet woods. You’ll learn how truffles are found, what makes them valuable, and how the dogs are trained to sniff them out. And when the dogs strike fungi gold, you even get to help dig.
Afterward, you’ll head back to Siena to taste local truffle products at a gourmet shop.
If you want something hands-on, outdoorsy, and truly local, this is one of the most unique things to do in Siena! Click here to book your truffle-hunting adventure from Siena!
12. Take a Day Trip to San Gimignano
I love San Gimignano – and I’ve visited many times on day trips from Florence and as a base for exploring Tuscany by car. It’s nicknamed the “Manhattan of Tuscany” for its medieval towers – and it’s just about the most charming village ever (especially once the midday crowds clear out).
If you love gelato, award-winning Gelateria Dondoli in Piazza della Cisterna will be your favorite part. (It’s mine too.)
After gelato, the key is to wander beyond the busy main street. Duck into the quiet alleys, pop into quiet wine bars, and take in the breathtaking views over the surrounding vineyards. The cathedral is worth a quick visit for its 14th-century frescoes, and climbing a tower rewards you with more beautiful views.
If you don’t have a rental car, book this small-group Chianti & San Gimignano sunset tour from Siena. It’s relaxed, scenic, and perfectly timed for seeing the town once the crowds start to thin!
13. Take a Day Trip to the Val d’Orcia
If you have an extra day in Siena, I’d send you to the Val d’Orcia – without question!
The Val d’Orcia is my favorite part of the Siena province, home to beautiful medieval villages like Pienza, Montepulciano, and Montalcino. This valley is the Tuscany you picture while planning your trip. Rolling hills, cypress-lined roads, medieval hill towns, world-class wine, and the best cheese ever.
If you’re confident driving in Italy, you can day trip to the Val d’Orcia by rental car. But if you’d rather relax, taste freely (no designated driver required!), and let someone else handle the logistics, these two guided day trips are great options.
You just have to decide whether you want a wine-forward day or a mix of wine, villages, and cheese!
- Brunello di Montalcino Wine Day Trip: This wine-forward day trip through the Tuscan hills will take you to three different wineries around Montalcino, with guided tastings of Rosso and Brunello di Montalcino. One stop includes a traditional Tuscan lunch at a family-run winery, plus a visit to the beautiful Abbey of Sant’Antimo. Book your Brunello di Montalcino wine day trip from Siena here.
- Montepulciano & Pienza Day Trip: This perfectly balanced Val d’Orcia day trip combines stunning scenery, food, and wine. You’ll explore the foodie village of Pienza, enjoy lunch and a pecorino cheese tasting at an organic dairy farm, then finish in Montepulciano with a winery visit and a cellar tasting of Vino Nobile di Montepulciano. (The photo above was taken inside an ancient wine cellar in Montepulciano – just to give you a sense of the atmosphere.) Book your Montepulciano and Pienza day trip from Siena here.
14. Explore Santa Maria della Scala
Have time for one more museum? Santa Maria della Scala sits directly across from the Duomo and was one of Europe’s oldest hospitals. For centuries, it cared for Via Francigena pilgrims, orphans, and the poor. Today, it’s a sprawling museum and cultural complex that offers a fascinating look at Siena beyond its churches and piazzas.
Inside, you’ll find beautifully preserved frescoes, Etruscan artifacts (including clay urns and pottery), Renaissance art, and exhibitions that explore Siena’s social history and civic life.
Entry is free every first Sunday of the month. Otherwise, tickets cost €8. Closed on Tuesdays.
15. Hike Along the Historic Via Francigena
For a different way to experience the Tuscan countryside from Siena, consider hiking a portion of the historic Via Francigena. This ancient pilgrimage route connected northern Europe to Rome and dates back to the 13th century. I haven’t done this hike yet, but it’s on my list for my upcoming trip to Siena!
One popular section runs from Siena to Monteriggioni. It’s a scenic rural path through vineyards, olive groves, and rolling hills. This route is nearly 13 miles long and takes most hikers about six hours to complete.
If you prefer organization and insight, this Tuscany hiking tour from Siena includes an expert guide, gentle trekking through the countryside (for roughly three hours, not six!), and a wine tasting in the medieval village of Monteriggioni at the end. If you ask me, it’s the perfect way to combine nature, history, and wine in one experience – and you return to Siena by train after the hike.
Click here to book your guided hike of the Via Francigena from Siena.
16. See a Performance at Teatro dei Rinnovati
And last but not least, if you’re staying overnight in Siena, check what’s on at Teatro dei Rinnovati.
This small, historic theater sits inside the Palazzo Pubblico on Piazza del Campo and dates back to the 14th century. It’s intimate, atmospheric, and very local. There are about ten concerts and performances per month, and some shows are free or very affordable.
This isn’t an essential thing to do in Siena, but it’s a fun evening option if you want something distinctly Sienese.
17. Go Hot Air Ballooning over Tuscany
Feeling adventurous? Go on a hot air balloon ride to see Tuscany’s lush countryside, hilltop towns, medieval castles, and vineyards from 2,000 feet above!
When you land, sparkling wine and a light Tuscan breakfast await. Make sure to dress warmly! It’s cold up there!
Click here to book your hot air balloon flight over Tuscany from Siena!
Planning Your Siena Visit
From the Duomo di Siena to the Piazza del Campo to local wineries, now you know all the best things to do in Siena – and why I think you can’t miss this beautiful city when you visit Tuscany next! Now, let’s quickly go over some must-know tips to help you plan your trip.
Best Time to Visit Siena
The best months to visit Siena are April, May, September, and October, when the weather is comfortably warm (roughly 60 to 80°F, or 16 to 27°C) and crowds are manageable.
My most recent visit was in May, and it was ideal. The Duomo had no line, museums were nearly empty, and even popular activities that usually require advance booking were available same-day.
Peak season (June through August) brings higher prices, heavier crowds, and hotter days, often climbing into the mid-to-high 80s °F (or 30 to 32°C) – especially busy around Palio dates.
November and December are lovely for a low-key city break. Winter in Siena means cold temps, fewer tourists, cozy trattorias, festive lights, and Christmas markets.
How to Take a Day Trip to Siena from Florence
If you’re spending three days in Florence (or more), Siena is one of the best day trips from Florence.
You can visit Siena independently by train and explore on foot. Since it’s a short journey, you’ll have plenty of free time in Siena. See my guide on how to day trip to Siena from Florence!
If you want to see more in one day, without dealing with logistics, book a guided tour. I’ve done this Siena, San Gimignano, Pisa, and Chianti winery day trip from Florence twice, and highly recommend it! You won’t have time to do all the best things to do in Siena (obviously!), but you will stroll the historic center, tour the Duomo, and have free time to try some panforte!
How Many Days to Spend in Siena
You can see most of Siena‘s highlights in a day, but if you stay for three days, you’ll be able to get through most of this list of the best things to do in Siena.
- One day in Siena: Enough time to see the highlights and understand why Siena matters. At the very least, you’ll go on this walking tour of the Centro Storico and the Duomo, and summit the Torre del Mangia.
- Two days in Siena: A slower pace, time for traditional meals, visiting museums without rushing, and drinking local wine.
- Three or more days in Siena: Extra time to see the surrounding countryside and even take a day trip to the Val d’Orcia.
Where to Stay in Siena (Quick Picks)
If you decide to stay overnight, here are my top picks for where to stay in Siena!
- Hotel Athena: Sweeping countryside views just outside the historic center
- Hotel Palazzo di Valli: Near the old town – and my personal favorite!
- Podere La Strega: A beautiful agriturismo near Siena – ideal if you rent a car
Siena, Italy: Travel FAQs
Midday can be busy due to day-trippers. Mornings and evenings are calm, quieter, and feel far more local.
Yes. Siena is an excellent base to explore the Val d’Orcia and nearby towns and cities like San Gimignano, Monteriggioni, Volterra, and even Florence by train.
Siena is known for Tuscan-style dishes like pici pasta, wild boar ragù, ribollita, local pecorino cheeses, cold cuts, and white beans. The most famous Sienese specialty is panforte di Siena (spiced fruitcake!).
Siena is very walkable, but it’s hilly in some places. Comfortable shoes are non-negotiable! These are my personal favorite tennis shoes for exploring Italian cities!
