The Best Things to Do in Siena, Italy: A First-Timer’s Guide

When it comes to the best things to do in Siena, Italy, this Tuscan city rivals Florence in its art and beauty. I spent four days here in the fall with my family, and Siena turned out to be the highlight of our two weeks in Tuscany. In this guide, I’m sharing the best of our time there, from sights and restaurants to where to stay and tips for visiting the cathedral complex.

If you’re planning a Tuscany itinerary, I can’t stress enough the importance of making time for Siena. I completely skipped it the first time I went to Tuscany, so this time I made sure to carve out the time. I’m so glad I did, because this masterpiece of a city absolutely wowed me.

The sense of civic pride here is everywhere; you see it in the architecture, the scale of sights like the Duomo and the Piazza del Campo, and the traditions. Siena is a city that, while small, is grand. You’ll find frescoed walls in chapels and museums, and sculptures tucked into public squares. And what better place to step into the Tuscan food scene than a city like Siena, chock-full of osterias and ristorantes.

I’ve also included helpful tips, like how to book the OPA SI Pass and the dates when the Duomo’s famous marble floor is fully uncovered. Both are worth knowing before you go.

Short on Time? Here Are My Top Picks for the Best Hotels and Things to Do in Siena:

Hotels

1. Grand Hotel Continental ($$$), for the best historic luxury in the heart of Siena
2. Hotel Athena ($$), for the best views
3. Hotel Certosa Di Maggiano ($$), for the best countryside-style historic retreat
4. La Terrazza Sul Campo ($$), for the best budget stay with piazza views

Airbnbs

1. 1 Bedroom Historic Apartment with Incredible View (Where We Stayed), for the best classic Siena stay with an unforgettable basilica view
2. 2 Bedroom Apartment near Piazza del Campo, for the best spacious setup for couples or friends who want to stay steps from it all
3. 2 Bedroom Apartment on Piazza del Campo with Terrace Views, for the best front-row seat to Siena’s most iconic square
4. 2 Bedroom Top-Floor Apartment with Rooftop Terrace, for the best morning coffee spot above the rooftops

Things to Do

1. Go Wine Tasting in Chianti or Montalcino
   • Castle and Chianti Wine Experience (5 hours)
   • Brunello di Montalcino Wine Tasting & Lunch in a Tuscan Castle (2 hours)
   • Small-Group Brunello di Montalcino Wine-Tasting Trip (Full day)
2. Skip the Line: Siena Duomo and City Walking Tour
3. Take a Small-Group Tuscan Cooking Class
4. Go Truffle Hunting in the Tuscan Countryside

Travel Tips

1. Rent a Car to Explore Tuscany — The best way to experience Tuscany is by driving yourself. We book our rental cars in Europe through Discover Cars, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt. Driving in Tuscany is straightforward, and having a car makes day trips from Siena much easier. Book your car with Discover Cars here.
2. Get Cell Data Before You Arrive — The easiest way to navigate Tuscany is with reliable cell data. We use Holafly unlimited data eSIMs for all international travel and recommend installing your eSIM before arrival so maps, ride-sharing, and directions work the moment you land. Pre-Purchase your Holafly eSIM here.

Helpful Guides to Plan Your Trip

If Siena is part of a broader Tuscany route, start with my Tuscany itinerary for the overall trip structure, then use my guide on where to stay in Tuscany to choose the right base. From there, my guides to San Gimignano, Montepulciano, and the Val d’Orcia (including Pienza and Montalcino) will help you plan countryside day trips, with route ideas, pacing, and where to stop for lunch or a winery visit.

For Florence, I have a 3-day Florence itinerary, a full Florence city guide covering the best things to do, and a guide on where to stay in Florence. And if Tuscany is part of a longer first trip to Italy, my 12-night first-timers Italy itinerary shows how it all fits into a broader Rome–Florence–countryside route. For more on where to go in Italy, start with my list of the best cities in Italy.

The Ultimate Guide to Siena, Italy: The Best Things to Do

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A Quick Look at Siena History

Siena’s history is rooted in its Etruscan origins and its rise as a powerful medieval city-state, shaped by trade, banking, and rivalry with Florence. In the 12th and 13th centuries, the city became one of Tuscany’s great civic powers. You can still see that legacy in its Gothic architecture, public squares, and carefully planned streets. Siena’s neighborhood life is organized through the 17 contrade and peaks during the Palio, the city’s famed race in Piazza del Campo. That commitment to art, ritual, and civic order is what gives Siena its distinctive character today. The city’s historic center is UNESCO-listed, and it remains one of the most rewarding places to visit in Italy.

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Siena Planning Tips Before You Arrive

Best Time to Visit Siena

My recommendation for popular destinations in Italy is to visit during late fall or early spring. Think months like October or November, or April and May.

How Much Time is Needed for Siena

While many people visit Siena as a half-day trip, I recommend spending one to two days there. You can see the main sights in a full day, but I think it’s really nice to break it up over two days if you have the time in your itinerary.

Getting to Siena

My recommendation is to rent a car to get to Siena, especially if it’s part of a larger Tuscany itinerary. Having a car makes it much easier to continue onward and take day trips. The most common public transport route is via Florence. You can take a direct train from Florence’s Santa Maria Novella Station to Siena Station. The journey typically takes about 1.5 hours and offers scenic views of the Tuscan countryside along the way.

If you’re driving, Siena can be reached via the Siena–Florence motorway and also takes about 1.5 hours. Just note that Siena’s historic center is a restricted traffic zone (ZTL), so you’ll want to park outside the walls and walk in.

Travel Tip: The city of Siena is HIGH up on the hill, requiring a steep walk (not recommended with luggage, during heat, or physical limitations). Parcheggio Santa Caterina is my preferred parking garage because it’s a short walk to this escalator, which takes you up the hill into the historic center.

Getting Around Siena

The historic center of Siena is completely accessible on foot (there are really no taxis at all here in the center). Staying centrally makes it very convenient to walk to the main sights.

Purchase the OPA SI Pass for Skip-the-Line Access & Ease

The best way to access the Siena Cathedral Complex is to pre-purchase the official OPA SI Pass (I did mine about a week in advance). The two main reasons are skip-the-line access and ease. It is valid for 3 days and includes one visit per site. You’ll redeem it at the Piazza del Duomo office ticket office. It includes access to:

• Siena Cathedral (Duomo)
• Piccolomini Library
• Museo dell’Opera (Cathedral Museum)
• Crypt and Baptistery of San Giovanni
• Facciatone (Panoramic viewpoint / only accessible with an OPA SI Pass)

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Where to Stay in Siena

My recommendation is to stay in the city center and park outside in the main parking garage, Parcheggio Santa Caterina, which is a short walk to this escalator. It means you can walk out of your accommodations and be within 10 minutes walk to the main sights. We stayed in this incredible Airbnb with beautiful views. Here are my top picks for where to stay in Siena:

Hotels

1. Grand Hotel Continental ($$$), for the top luxury boutique stay just steps from Piazza del Campo and the Duomo
2. Hotel Athena ($$), for the best value mid-range stay with panoramic terrace views near the Duomo
3. Hotel Certosa Di Maggiano ($$), for the best serene luxury stay outside the walls with gardens, pool, and historic monastery character
4. La Terrazza Sul Campo ($$), for the best budget-friendly stay right on Piazza del Campo with terrace views

Airbnbs

1. 1 Bedroom Historic Apartment with Incredible View (Where We Stayed), for the best classic Siena stay with an unforgettable basilica view
2. 2 Bedroom Apartment near Piazza del Campo, for the best spacious setup for couples or friends who want to stay steps from it all
3. 2 Bedroom Apartment on Piazza del Campo with Terrace Views, for the best front-row seat to Siena’s most iconic square
4. 2 Bedroom Top-Floor Apartment with Rooftop Terrace, for the best morning coffee spot above the rooftops

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The Best Things to Do in Siena, Italy

Siena is best experienced at an unhurried pace. Start with the essentials like Piazza del Campo and the Duomo, then weave in museums, viewpoints, and long meals as you go. Below are the very best things to do in Siena, along with a few small tips to help you plan your days well.

Stroll Through Piazza del Campo

The heart of Siena is Piazza del Campo. I felt instantly transported to ancient times the first time I stepped through the arches into the grand piazza. The piazza is one of the most immaculate squares in Italy, and it still functions exactly as it should: a place to gather, linger, and people-watch. Restaurants ring the edge, all facing Palazzo Pubblico and the medieval Torre del Mangia above.

You’ll find people sitting on the steps with a sandwich, soaking in the scene. It’s busiest midday, so I recommend coming early in the morning to experience it before the crowds. While you’re here, look for Fonte Gaia, the sculpted fountain at the top of the square, where you can drink the water.

From Piazza del Campo, you can visit Palazzo Pubblico and climb the Torre del Mangia. Tickets are sold day-of only (no advance reservations), with timed entry in small groups. So it’s worth doing this early if it’s on your list. The climb is over 400 steps, and the views are meant to be some of the best in Siena (it was closed when I visited).

Additional Information on Climbing Torre del Mangia

• Tickets: €10 (adults)
• Entry: Timed slots in small groups
• Hours:
  • Mar 1–Oct 31: 10:00 am–7:00 pm (daily)
  • Nov 1–Feb 28: 10:00 am–1:00 pm, 1:45 pm–3:15 pm (daily)

Visit the Duomo di Siena

The grand star of Siena is no doubt the Duomo. With its two-toned marble facade and Romanesque-Gothic architecture, the Duomo is one of the most outstanding churches in all of Italy.

While the facade feels incredibly intricate, the real star of the show is inside. As you step into the impressive church, draw your attention to the floors. Created over the 14th to 19th centuries, artists etched into the marble to create 56 inlay panels of detailed scenes. From biblical scenes to wars, to prophecies and heroes, the floor feels like a storybook etched into stone forever. The sections are covered for protection most of the year. But during the annual uncovering, you can see the full mosaic floor in all its detail. I happened to visit during the uncovering, and it was incredible to see.

Travel Tip: If seeing Siena’s famous marble mosaic floor uncovered is on your list, plan your visit around the official “pavimento scoperto” windows: June 27–July 31, 2026 and August 18–October 15, 2026 (hours also extend during this period). Confirm the current dates here.

As you admire the marble floor mosaics, don’t miss the colorful and intricate Piccolomini Library, which was my favorite stop in the cathedral complex. Entry is included with both a standard cathedral ticket and the OPA SI Pass. Built in the early 16th century to house Pope Pius II’s book collection, the library is best known for its cycle of frescoes by Pinturicchio, which narrate the pope’s life as a sequence of political, religious, and diplomatic episodes. Rather than functioning as a working library, the space was conceived as a monument to learning, lineage, and patronage.

There are two primary options for accessing the Cathedral Complex. You can buy a standard cathedral ticket, or go with the official OPA SI Pass, which covers the full Cathedral Complex with skip-the-line access (more on this below).

Travel Tip: I did the Porta del Cielo experience at the Duomo, a guided small-group tour that takes you up into the upper levels of the cathedral. You’ll get close-up views of the dome and murals and see the interior from above, with a short stretch along a narrow exterior passageway. Personally, I don’t think it’s worth the extra time. I’d prioritize climbing the Facciatone instead for better views. If you do want to do Porta del Cielo (Gates of Heaven), you can add it to your OPA SI Pass or buy a separate ticket at the Crypt ticket office.

Important Duomo Visiting Information

• Hours
  • Mon–Sat:
    • Apr 1–Oct 31: 10:00 am–7:00 pm
    • Nov 1–Mar 31: 10:30 am–5:30 pm
  • Sun: 1:30 pm–6:00 pm
  • Note: Hours can shift for religious services and special events.
• Tickets
  • Duomo-only entry (cathedral interior)
    • €5 (Jan 1–Jun 26, Aug 1–17, Oct 16–Dec 31)
    • €8 (During the marble floor uncovering period)
  • OPA SI Pass: Duomo entry included
• Dress code: Dress appropriately for a religious site; no hats inside.

Explore and Shop Your Way Through the Centro Storico of Siena

If there’s one way to experience Siena’s historic heartbeat, it’s to wander the Centro Storico. Go once in the morning to miss the crowds, and a second later to go explore the shops. The lanes twist and climb, archways cut overhead, and every turn seems to reveal another small piazza or stone staircase. Use Piazza del Campo as your anchor point, then let yourself get a little lost.

Along the way, there are a few standout stops if you’re shopping for gifts. Antica Drogheria Manganelli 1879 is an old-world Italian grocery store that I could have filled my entire suitcase with. Think Sienese food, dried goods, panforte, and cured products. Just down the street, Manufactus is a leather shop that does customized leather goods like notebooks, journals, and more. They can personalize items, which make great gifts for friends and family.

Across the street, you’ll find Cappelleria Bertacchi, a one-of-a-kind hat shop. I thoroughly enjoyed the rainbow of colors at Ceramiche Antica Siena by Martini Marisa, the spot for all things ceramics. And for those who have a sweet tooth, keep an eye out for Pasticceria Nannini Conca D’Oro, for all things pastry.

Climb the Facciatone Viewpoint for Incredible Views

If I had to pick one standout experience in Siena, it would be climbing the Facciatone viewpoint. And while Siena is chock full of viewpoints, this one in particular gives an unobstructed view of the Duomo and straight into the city center.

I happened to time it with sunset, so I was extra lucky to soak in the purple and pink hues as the city lights began to turn on. What you may not know is that the Facciatone is the roof of Siena’s unfinished “new cathedral” project. The Facciatone is in the same building as the Museo dell’Opera. Head up a few floors to access. As part of the OPA SI Pass, you can access it in a small group setting.

Important Facciatone Visiting Information

• Tickets: OPA SI Pass only
• Hours:
  • Apr 1–Oct 31: 10:00 am–7:00 pm
  • Nov 1–Mar 31: 10:30 am–5:30 pm
• Crowds: Most popular late afternoon. Entry is in small groups (about 20), with one group going up as another comes down. For the calmest experience, go at the earliest time slot.

Make Your Way Through the Museums of Siena

With a few days in Siena, you can really dive into the city’s art and history through its museums. When I think about which ones I would prioritize, I’ve stack-ranked them in terms of the most inviting, grand, and worth the time investment.

Santa Maria Della Scala

If I had to pick one, it would be Santa Maria della Scala, housed in a former hospital just opposite the Duomo. With its frescoes and grand halls, it’s one of the best museum visits in Siena. Founded in the Middle Ages, it functioned for centuries as a place of care for pilgrims, the poor, and the sick, reflecting the city’s long tradition of public welfare. Today it operates as a museum and cultural center, with frescoed halls, chapels, and underground spaces that document the city’s social, religious, and artistic life.

Museo dell’Opera

The Museo dell’Opera del Duomo houses many of the cathedral’s original artworks and architectural elements, preserving the artistic program that shaped the Duomo over centuries. It’s best known for Duccio di Buoninsegna’s Maestà, one of the foundational works of Italian painting, along with sculptures by Giovanni Pisano and fragments from the cathedral facade.

Museo Civico

Located inside the Palazzo Pubblico in Piazza del Campo, the Museo Civico preserves the visual record of Siena’s republican government. Its core works include Ambrogio Lorenzetti’s Allegory of Good and Bad Government, a rare medieval fresco cycle that links political authority to civic responsibility and daily life. The museum’s rooms, once used for official assemblies, are decorated with frescoes that reflect Siena’s independence and civic ideals at the height of its power.

Pinacoteca Nazionale

The Pinacoteca Nazionale of Siena presents the development of Sienese painting from the 13th to the 15th centuries, highlighting a distinct tradition shaped by devotion, line, and color. Housed in the former palaces of the Brigidi and Buonsignori families, the collection includes works by Duccio, Simone Martini, and the Lorenzetti brothers.

Walk to Basilica Cateriniana San Domenico

For a nice stroll, head to Basilica Cateriniana San Domenico. The focal point across the city from the Duomo is this red-brick Dominican church. Built in the 13th century, it houses relics and artworks associated with Saint Catherine, including frescoes and altarpieces depicting scenes from her life and visions. The architecture is intentionally austere, reflecting the Dominican order’s emphasis on preaching and contemplation.

Step into the Crypt and Baptistery of San Giovanni

As part of the Siena Cathedral Complex, don’t miss the Crypt and the Baptistery of San Giovanni. You’ll only need about 15 minutes to visit the baptistery, but it is well worth the time to see the grandeur there. Built in the 14th century, the baptistery has an octagonal plan and Gothic architecture designed to elevate the ritual of baptism. The interior is renowned for its marble mosaic floor and sculpted baptismal font, featuring panels by artists such as Donatello, Jacopo della Quercia, and Lorenzo Ghiberti.

Access: Included with the OPA SI Pass.
Hours: April 1–October 31, 10 am–7 pm. November 1–March 31, 10:30 am–5:30 pm.

Visit Santuario Casa di Santa Caterina

The Santuario Casa di Santa Caterina is one of Siena’s most revered religious sites. It was built around the birthplace of Saint Catherine of Siena, the city’s beloved mystic and Doctor of the Church. Today, it’s a layered complex of chapels and devotional spaces, with frescoes and relics tied to her life and spiritual beginnings. Pilgrims and visitors alike are drawn to the sanctuary not only for its spiritual importance but also for its serene atmosphere, which invites reflection and pause.

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Where to Eat in Siena

I feel that the best way to experience Siena and its rich culture is by eating your way through the city. There are a handful of standout restaurants, and all of them require reservations year-round. Walk-ins are practically nonexistent at the good restaurants, so absolutely book ahead.

La Taverna di San Giuseppe

Set in an ancient Etruscan cellar, La Taverna di San Giuseppe is one of my favorite lunches in the city. The lines of people hoping for a table without a reservation tell you how popular it is! Their house-made pastas, like the pici carbonara and the pici with truffle, were absolutely amazing.

Osteria Permalico

For traditional Tuscan cuisine, the brick-laden Osteria Permalico was our favorite. The beef tartar was one of the best of the trip, followed by hearty hand-cut pici pasta in a simple tomato sauce.

Torrefazione Fiorella

When it comes to coffee, the best one in the city is Torrefazione Fiorella. It’s open daily except Sundays, and the espresso here is really great.

Osteria degli Svitati

One of those laidback restaurants in town for classic comfort food. Go for pastas with ragus and simple sauces, to classic meatballs and charcuterie plates.

Du’ Cose da Berna

I got a sandwich at Du’ Cose da Berna twice it was so good. It’s a classic spot that stays open late into the night (our apartment was above it). Expect fun combinations like ricotta with honey and Tuscan salami, plus fresh Negronis for only 5 euros.

Ristorante/Pizzeria All’Orto de’ Pecci

Come here for a lovely out-of-the-city meal. Set on a farm, All’Orto de’ Pecci feels like a transportive meal with fresh foods and good pizza.

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Where to Take a Day Trip From Siena

Go an hour in any direction, and you’ll find somewhere amazing to visit. Siena makes such a great two- to four-night base for exploring Tuscany. Below are a few of my favorite ideas, plus a couple of standout tours to consider.

Wine Experiences: Chianti or Brunello di Montalcino

For all things wine, look no further than Chianti or Montalcino. Both are under an hour from Siena, and each drops you into one of Italy’s most celebrated wine regions. You’ll be tasting in DOCG territory, with Chianti Classico to the north and Brunello di Montalcino to the south.

You can absolutely self-explore by car and hop between wineries (Antinori nel Chianti Classico, Castello di Verrazzano, and Castello di Volpaia are all great options). If you’d rather not think through logistics, a small group tour can be an easy way to visit a few estates, enjoy a long lunch, and leave the driving to someone else. Here are a few of the best tours from Siena that dive deep into wine country:

• Castle and Chianti Wine Experience (5 hours)
• Brunello Wine Tasting & Lunch in a Tuscan Castle (2 hours)
• Small-Group Brunello di Montalcino Wine-Tasting Trip (Full day)

Val d’Orcia

One region in particular that’s only about an hour from Siena is the Val d’Orcia. This is where you’ll find famous villages like Pienza, Montalcino, Montepulciano, and Bagno Vignoni. You can see a good portion of it in a day, even though it easily deserves longer (we based ourselves here for two weeks during our last trip and loved it).

If you’re choosing just a couple of stops, I’d focus on Pienza and Montalcino. Both are charming in different ways, and they make a great pairing for a day of scenic drives, long agriturismo lunches, and a winery stop or two. See my full Val d’Orcia guide to plan your time.

San Gimignano

Only 45 minutes away, San Gimignano is an easy and popular day trip from Siena. Known as Tuscany’s “village of towers,” it’s one of the most established towns in Tuscany and a lovely stop for an afternoon. Stroll the medieval center, try world-famous gelato, and settle in for a meal at one of the many osterias or trattorias in town.

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