Things to Do in Siena Tuscany: The Ultimate Guide

Siena transports visitors back to the Middle Ages better than almost any other Italian city. The historic centre, remarkably preserved since the 14th century, showcases stunning Gothic architecture, world-class art, and a vibrant local culture that celebrates centuries-old traditions like the famous Palio horse race.

Unlike Florence, Siena maintains an intimate, manageable scale whilst offering equally impressive cultural treasures. The city's three hilltop districts wind around spectacular views, medieval towers, and hidden piazzas where locals still gather for their evening passeggiata.

1. Marvel at Piazza del Campo

The beating heart of Siena, Piazza del Campo ranks amongst Italy's most beautiful squares. Its distinctive shell-shaped design, divided into nine sections representing the medieval Council of Nine, creates a natural amphitheatre that draws both visitors and locals throughout the day.

The square's unique sloping design was completed in 1349 and has served as Siena's social and civic centre ever since. Surrounded by elegant medieval palaces built according to strict 13th-century regulations, the burnt-orange brick paving creates a warm, welcoming atmosphere.

What to see:

• Palazzo Pubblico – The magnificent Gothic town hall, still functioning as Siena's municipal building
• Fonte Gaia – The ornate Renaissance fountain featuring intricate marble sculptures
• Loggia della Mercanzia – The 15th-century merchants' loggia marking the intersection of Siena's three main streets

Top tip: Visit early morning or late evening to avoid crowds and experience the square's magical acoustics as conversation echoes around its curved walls.

2. Climb Torre del Mangia

Rising 102 metres above Piazza del Campo, Torre del Mangia offers breathtaking panoramic views across Siena and the Tuscan countryside. As Italy's third-tallest historic tower, it was deliberately built to match the height of the Duomo's bell tower, symbolising the balance between civic and religious power in medieval Siena.

The tower takes its curious name from its first bell-ringer, Giovanni di Balduccio, nicknamed "Mangiaguadagni" (earnings eater) for his spendthrift habits.

Essential information:

• Height: 102 metres (over 400 steps)
• Entry fee: €10 standalone or included in combination tickets
• Hours: 10am-7pm (March-October), 10am-4pm (November-February)
• Tickets: Purchase in person only at Palazzo Pubblico ticket office

Important: Entry operates on timed slots with limited capacity. Arrive early to secure your preferred time, especially during peak season. The climb requires moderate fitness and isn't suitable for those with mobility issues or severe vertigo.

3. Explore the Magnificent Duomo di Siena

Siena Cathedral stands as an absolute masterpiece of Italian Gothic architecture. The striking façade features alternating bands of white and dark green serpentinite marble creating distinctive "zebra stripes," whilst intricate pink marble sculptures and golden mosaics adorn the upper sections.

Inside, prepare to be astounded by one of Italy's most extraordinary artistic achievements: the marble inlay floor featuring 56 panels depicting biblical scenes, ancient prophecies, and allegorical figures. Created between the 14th and 19th centuries using the graffito technique, these detailed marble mosaics create an unparalleled stone tapestry.

Must-see features:

• The spectacular marble floor (fully uncovered mid-August to mid-October)
• Piccolomini Library with vibrant Renaissance frescoes by Pinturicchio
• Sculptures by Donatello, Michelangelo, and Bernini
• The Chigi Chapel designed by Bernini

Visiting information:

• Hours: Monday-Saturday 10am-7pm (April-October), 10:30am-5:30pm (November-March)
• Entry fee: €5-8 depending on season
• Skip-the-line tickets: Highly recommended during summer months

Pro tip: The floor uncovering typically runs from mid-August through September, attracting significantly larger crowds. Visit at opening time for the best experience.

4. Discover Hidden Treasures at Santa Maria della Scala

Directly opposite the Duomo, this vast complex served as one of Europe's oldest hospitals for over 900 years until the 1980s. Today, Santa Maria della Scala operates as an extraordinary museum and cultural centre revealing layers of Sienese history through art, archaeology, and architecture.

The highlight is the Pellegrinaio Hall, adorned with stunning 15th-century frescoes depicting acts of charity and the hospital's role in caring for pilgrims, orphans, and the sick. Beneath the main complex, explore excavated tunnels, ancient foundations, and a remarkable crypt discovered during renovations.

What to explore:

• Renaissance frescoes by Vecchietta and Beccafumi
• Archaeological collections spanning Etruscan to medieval periods
• The evocative crypt with 13th-century frescoes
• Contemporary art exhibitions in restored hospital wards

Budget tip: Santa Maria della Scala offers excellent value, typically costing €9 and providing 2-3 hours of fascinating exploration away from the crowds.

5. Visit the Cathedral Complex: Baptistry, Crypt & Museum

The OPA SI Pass grants access to six sites within the Cathedral Complex, representing exceptional value for culture enthusiasts.

Baptistery of San Giovanni: Hidden down steep steps behind the Duomo, this beautifully frescoed space features a magnificent hexagonal marble font with gilded bronze panels by Renaissance masters including Donatello, Ghiberti, and Jacopo della Quercia.

The Crypt: Only discovered in 1999, these underground chambers contain remarkably preserved 13th-century frescoes depicting Old Testament scenes in vivid colours.

Museo dell'Opera: Houses the original sculptures from the Duomo's exterior, including works by Giovanni Pisano and Donatello. The crown jewel is Duccio's monumental Maestà altarpiece (1308-1311), displayed in a climate-controlled gallery.

Facciatone Viewpoint: Climb the ruins of the "New Cathedral" (an ambitious 14th-century expansion abandoned after the Black Death) for stunning eye-level views of the Duomo's striped bell tower and marble façade.

Pass details:

• OPA SI Pass: €13-15 (season dependent)
• Validity: 72 hours from first use
• Includes: Cathedral, Baptistry, Crypt, Museum, Facciatone, Oratory of San Bernardino

6. Experience the Museo Civico

Located inside Palazzo Pubblico, the Museo Civico showcases Siena's artistic heritage through magnificent frescoed halls. The highlight is Ambrogio Lorenzetti's breathtaking Allegory of Good and Bad Government (1338-1339), one of medieval Europe's most important secular frescoes.

Other treasures include Simone Martini's Maestà (1315) and works by Taddeo di Bartolo. Don't miss the panoramic terrace offering excellent views across Siena.

Combined ticket: Museo Civico admission includes Torre del Mangia access, making it excellent value at €20.

7. Wander Through the Contrade

Siena's 17 historic contrade (neighbourhoods) form the backbone of local identity. Each contrada has its own symbol (ranging from the Giraffe to the Porcupine), church, museum, and social club, with fierce rivalries coming to life during Palio preparations.

Stroll through different neighbourhoods spotting their distinctive emblems on fountains, flags, and street plaques. Several contrade open their museums and churches to visitors, offering insight into centuries-old traditions.

Top contrade to explore:

• Oca (Goose) – Beautiful fountain near the Duomo
• Drago (Dragon) – Charming streets near Porta Romana
• Torre (Tower) – Historic neighbourhood with medieval towers

8. Attend the Palio di Siena

The Palio represents one of Europe's most spectacular medieval traditions. Twice yearly (2nd July and 16th August), ten contrade compete in a breakneck bareback horse race around Piazza del Campo, with festivities spanning four days.

This isn't a tourist spectacle but a deeply meaningful event for Sienese residents. The winning contrada celebrates for months, whilst losers plot their revenge for the next race.

Attending the Palio:

• Free standing: Arrive very early (by 2pm for 7pm race) to secure a spot in the Campo's centre
• Paid seating: Expensive tickets (€200+) for balconies and stands, book months ahead
• Experience: Witness trial races in the days before the main event
• Alternative: Visit during Palio time to see the city decorated in contrada colours

9. Seek Out the Best Viewpoints

Siena's hilltop location provides numerous spectacular vantage points:

Facciatone Panorama: Eye-level views of the Duomo's bell tower (OPA SI Pass required)

Torre del Mangia: 360-degree panoramas across Siena and surrounding countryside

San Domenico Terrace: Free viewpoint behind the Basilica with beautiful sunset views

Monastery of St Augustine: Hidden gem with peaceful park and stunning vistas

Fortezza Medicea: Renaissance fortress with rampart walks and countryside views

Orto de' Pecci: Large park below the walls perfect for picnics and children

10. Indulge in Sienese Cuisine

Siena's culinary traditions centre on hearty, honest flavours:

Must-try dishes:

• Pici cacio e pepe – Thick hand-rolled pasta with pecorino cheese and black pepper
• Pappardelle al cinghiale – Wide pasta ribbons with wild boar ragù
• Ribollita – Thick Tuscan bread soup with vegetables and beans
• Bistecca alla Fiorentina – Grilled T-bone steak (when done properly)

Traditional sweets:

• Panforte – Dense spiced fruit and nut cake
• Ricciarelli – Soft almond biscuits
• Cavallucci – Anise-flavoured walnut biscuits
• Cantucci con Vin Santo – Almond biscuits dunked in sweet wine

Recommended restaurants:

• Osteria Le Logge – Refined Tuscan cuisine in elegant setting
• La Taverna di San Giuseppe – Traditional dishes in medieval cellar
• Ristorante All'Orto de' Pecci – Farm-to-table dining outside the walls
• Tre Cristi – Authentic neighbourhood restaurant with tasting menus

Budget-friendly options:

• Antica Pizzicheria – Legendary sandwich shop on Via di Città
• La Prosciutteria – Charcuterie boards and local wines

Chianti Wine Region (30-40 minutes)

The Chianti Classico wine region sprawls between Siena and Florence, offering quintessential Tuscan landscapes of rolling vineyards, cypress-lined roads, and medieval villages.

Top wineries to visit:

• Castello di Brolio – Historic castle with wine museum and tastings
• Castello di Ama – Contemporary art installations amongst vineyards
• Antinori nel Chianti Classico – Architectural masterpiece winery
• Castello di Verrazzano – Beautiful estate with tours and lunches

Charming villages:

• Greve in Chianti – Market town and wine centre
• Radda in Chianti – Perfectly preserved medieval village
• Castellina in Chianti – Fortress town with Etruscan heritage

Val d'Orcia (45-60 minutes)

The Val d'Orcia UNESCO World Heritage landscape epitomises the Tuscan idyll with its rolling hills, isolated farmhouses, and hilltop towns.

Must-see locations:

• Pienza – Renaissance "ideal city" with spectacular views and pecorino cheese
• Montalcino – Medieval fortress town producing Brunello wine
• Montepulciano – Elegant hilltown with Vino Nobile and magnificent churches
• Bagno Vignoni – Thermal village built around a Roman pool
• Cappella della Madonna di Vitaleta – Iconic chapel photographed at sunrise

Scenic drives: Follow the SP146 and SP88 through cypress-lined curves and golden wheat fields.

San Gimignano (45 minutes)

The "Medieval Manhattan" bristles with 14 surviving towers creating a distinctive skyline. This UNESCO World Heritage town offers:

• Piazza della Cisterna with ancient well
• Collegiate Church with stunning frescoes
• Torre Grossa (tallest tower open to climb)
• Vernaccia wine tasting
• World-class gelato from Gelateria Dondoli

Monteriggioni (20 minutes)

A perfectly preserved walled village perched on a hilltop, Monteriggioni can be explored in an hour but offers excellent restaurants for longer stops. Walk the medieval ramparts and enjoy views across the countryside.

Florence (1 hour)

While Florence deserves multiple days, a day trip from Siena allows you to experience the Uffizi Gallery, Duomo, Ponte Vecchio, and Accademia (home to Michelangelo's David).

Trains run hourly, taking 1.5 hours, whilst the rapido bus takes 1 hour 15 minutes.

Lucca (1.5 hours)

Completely encircled by intact Renaissance walls you can cycle atop, Lucca charms visitors with its amphitheatre piazza, stunning churches, and Puccini heritage.

Cooking Classes

Learn traditional Tuscan cuisine from locals:

• Small-group pasta classes – Make pici, ravioli, and tiramisu from scratch
• Farm visits with cooking – Tenuta Chiudendone offers full-day farm-to-table experiences
• Professional chef classes – Four-course menu preparation in Siena's centre

Wine Tours

Experience Tuscany's renowned wines:

• Brunello di Montalcino tours – Visit three wineries producing this prestigious DOCG wine
• Chianti Classico estates – Explore castle wineries with tastings and lunches
• Wine education courses – Learn tasting techniques from sommeliers
• Vespa wine tours – Explore countryside on vintage scooters with winery stops

Enotecas (Wine Bars)

Sample regional wines in atmospheric settings:

• Enoteca I Terzi – Extensive wine list with seasonal plates
• Enoteca Italiana – Inside the Fortezza Medicea with 1,000+ Italian wines
• Cantina del Brunello – Specialist in Montalcino wines

Practical Information

Getting to Siena

By train: Siena's station sits 2km below the historic centre. Frequent services from Florence (1.5 hours, €10-14). Take local bus, taxi, or walk uphill.

By bus: Tiemme rapido buses from Florence (1 hour 15 minutes) drop passengers in the centre near La Lizza or Piazza Gramsci.

By car: A1 motorway to Firenze-Certosa exit, then Siena-Firenze highway. Park outside the ZTL (limited traffic zone) in designated car parks:

• Parcheggio Il Campo (near Porta Tufi)
• Parcheggio Santa Caterina/Fontebranda (escalator to centre)
• Parcheggio Stadio (near Fortezza Medicea)

Getting Around Siena

The historic centre is entirely pedestrianised and compact. Expect cobblestones, hills, and stairs. Wear comfortable walking shoes.

Local buses: Connect car parks and train station to the centre (€1.50 per journey).

Best Time to Visit

Spring (April-May): Pleasant temperatures (15-22°C), blooming countryside, fewer crowds. Easter can be busy.

Summer (June-August): Hot (28-35°C), crowded, especially around Palio dates. Book accommodation well ahead. Cathedral floor partially uncovered.

Autumn (September-October): Ideal weather (18-25°C), harvest season, full cathedral floor display, wine festivals. Peak season for visitors.

Winter (November-March): Quieter, colder (5-12°C), some attractions have reduced hours. Fewer day-trippers make for authentic local atmosphere.

How Long to Stay

Day trip (6-8 hours): Duomo, Piazza del Campo, Torre del Mangia, Santa Maria della Scala, quick meal

Two days: Above plus Museum dell'Opera, Baptistry & Crypt, multiple restaurants, evening atmosphere, leisurely wandering

Three days: Add wine tour or Val d'Orcia day trip, cooking class, thorough exploration of contrade and museums

Four+ days: Perfect base for exploring wider Tuscany whilst enjoying Siena's relaxed pace

Essential Phrases

• Buongiorno (bwon-JOR-no) – Good morning
• Grazie (GRAT-zee-eh) – Thank you
• Per favore (pear fa-VOR-eh) – Please
• Quanto costa? (KWAN-toh KOS-ta) – How much does it cost?
• Il conto, per favore – The bill, please
• Dov'è...? – Where is...?