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A Medieval Masterpiece: Three Days in Siena

Gothic Splendor, Renaissance Art, and Tuscan Traditions

Trip Overview

Immerse yourself in one of Italy's most perfectly preserved medieval cities with this three-day journey through Siena's artistic and architectural treasures. This itinerary balances the city's world-famous landmarks—including the shell-shaped Piazza del Campo and the magnificent Siena Cathedral—with quieter corners where local life unfolds. You'll explore Gothic palaces, climb ancient towers for panoramic views, discover masterpiece-filled museums, and savor authentic Tuscan cuisine in atmospheric trattorias. The compact historic center makes walking a pleasure, while the leisurely pace allows time to absorb the city's unique atmosphere. Beyond sightseeing, you'll experience the proud Sienese culture, from traditional crafts to the legendary Palio horse race traditions that define this captivating Tuscan gem.

Pace
Moderate
Daily Budget
$120-180 per day
Best Seasons
April-June and September-October for pleasant weather; avoid mid-August heat
Ideal For
First-time visitors to Tuscany, Art and architecture enthusiasts, History buffs, Couples seeking romantic getaways, Food and wine lovers

Day-by-Day Itinerary

1

The Heart of Medieval Siena

Historic Center
Begin your Sienese adventure in the iconic Piazza del Campo before exploring the magnificent cathedral complex and climbing for unforgettable city views.
Morning
Piazza del Campo and Palazzo Pubblico
Start at the breathtaking shell-shaped Piazza del Campo, one of Europe's greatest medieval squares. Admire the elegant Palazzo Pubblico with its soaring Torre del Mangia tower. Visit the civic museum inside the palazzo to see extraordinary frescoes including Ambrogio Lorenzetti's Allegory of Good and Bad Government. If you're feeling energetic, climb the 400 steps of the tower for spectacular panoramic views across Siena's terracotta rooftops to the Tuscan countryside beyond.
3-4 hours $15-25
Arrive early to avoid crowds at the tower; combined tickets available for multiple sites
Lunch
A traditional trattoria near the Campo serving pici pasta and local specialties
Tuscan Mid-range
Afternoon
Siena Cathedral and Opera della Metropolitana
Marvel at the stunning Siena Cathedral, a Gothic masterpiece with its striking black-and-white marble facade and ornate interior featuring works by Michelangelo, Donatello, and Bernini. Don't miss the intricate marble floor panels (uncovered seasonally). Visit the Opera della Metropolitana museum to see Duccio's magnificent Maestà altarpiece and climb the Facciatone for another perspective on the city. The Piccolomini Library inside the cathedral showcases brilliant Renaissance frescoes in jewel-like colors.
3 hours $20-30
Purchase the Opa Si Pass for access to cathedral complex sites; book online to skip ticket lines
Evening
Sunset aperitivo and dinner in the historic center
Enjoy aperitivo at a wine bar in the medieval streets, followed by dinner at a family-run osteria featuring Florentine steak and Chianti Classico

Where to Stay Tonight

Historic Center near Piazza del Campo (A charming three-star hotel or B&B in a converted medieval building)

Central location puts you within walking distance of all major attractions and lets you experience the atmospheric historic streets after day-trippers leave

The cathedral floor's elaborate marble panels are only fully uncovered from late June to late October—plan accordingly if this is a priority for you
Day 1 Budget: $140-200
2

Art Treasures and Sacred Spaces

Historic Center and Northern Quarter
Dive deeper into Siena's artistic heritage at world-class museums and visit the city's most important religious sites beyond the cathedral.
Morning
Pinacoteca Nazionale di Siena
Explore this exceptional art gallery housed in the Gothic Palazzo Brigidi and Palazzo Buonsignori. The collection showcases the golden age of Sienese painting from the 13th to 16th centuries, featuring works by Duccio, Simone Martini, and the Lorenzetti brothers. The chronologically arranged galleries reveal how Siena's artists developed their distinctive style, characterized by elegant lines, rich colors, and spiritual intensity. The intimate scale allows you to appreciate these masterpieces up close in a less crowded setting than many Italian museums.
2-3 hours $10-15
Lunch
A casual enoteca with outdoor seating serving Tuscan antipasti platters and local wines
Tuscan wine bar fare Mid-range
Afternoon
Basilica Cateriniana San Domenico and surrounding area
Visit this imposing brick basilica dedicated to St. Catherine of Siena, Italy's patron saint. The austere interior contains precious relics and beautiful frescoes depicting the saint's life. From the basilica's position on a hill, enjoy wonderful views back toward the cathedral. Afterward, stroll through the surrounding neighborhood to Palazzo Salimbeni, the elegant Renaissance headquarters of the world's oldest bank, and explore the quieter streets where local Sienese life unfolds away from the main tourist routes.
2-3 hours $5-10
Evening
Explore the Terzo di Camollia neighborhood and dinner
Walk through the northern district past Porta Camollia, the historic city gate, then dine at a neighborhood restaurant frequented by locals serving seasonal Tuscan dishes

Where to Stay Tonight

Historic Center near Piazza del Campo (Same accommodation as Day 1)

Staying in the same location eliminates check-in/check-out time and lets you settle in and discover favorite local spots

Many churches close from 12:30-3:30 PM for riposo—plan your visits accordingly and use midday for lunch and museum visits
Day 2 Budget: $120-170
3

Hidden Corners and Panoramic Views

Historic Center and City Walls
Discover Siena's lesser-known treasures, walk the ancient city walls, and experience local traditions before departing.
Morning
Fortezza Medicea and city walls walk
Begin at the Fortezza Medicea, a 16th-century Medici fortress that now houses a wine center and public gardens. The ramparts offer peaceful walking paths with excellent views over the city and surrounding hills. Continue along sections of the medieval city walls, passing through ancient gates like Porta Pispini and Porta Tufi. This walk reveals Siena's impressive defensive architecture and provides a different perspective on the city's topography, showing how it sits atop three hills with valleys between.
2-3 hours $5-10
Lunch
A simple lunch at a bakery or market vendor featuring panforte, ricciarelli cookies, and porchetta sandwiches
Sienese street food and pastries Budget
Afternoon
San Clemente in Santa Maria dei Servi and Palazzo Piccolomini
Visit the Church of Santa Maria dei Servi, perched on a hill in the southern part of the city with a lovely terrace offering views toward the countryside. Inside, admire important artworks in a peaceful setting often overlooked by tourists. Then explore Palazzo Piccolomini, a Renaissance palace housing the State Archives with fascinating historical documents. If time permits, visit the unique Siena Synagogue to learn about the city's Jewish heritage, or explore the Musei dell'Accademia dei Fisiocritici for its quirky natural history collections.
2-3 hours $10-15
Evening
Final evening stroll and farewell dinner
Return to Piazza del Campo for a final sunset view from the square, then enjoy a celebratory dinner at an upscale restaurant featuring contemporary takes on Tuscan classics paired with Brunello di Montalcino

Where to Stay Tonight

Historic Center near Piazza del Campo (Same accommodation as previous nights)

Final night in your established base before departure

Stop at a specialty shop to buy authentic panforte and cantucci to take home—these traditional Sienese sweets make excellent gifts and travel well
Day 3 Budget: $130-180

Practical Information

Getting Around

Siena's historic center is compact and entirely walkable—comfortable shoes are essential for the hilly cobblestone streets. The city is car-free in the center, with parking available at designated lots outside the walls (Santa Caterina, Il Campo, and Stadio are convenient). If arriving by train, take a local bus or taxi from the station to the center (uphill, 20-minute walk). For day trips to nearby towns, regional buses depart from Piazza Gramsci. Within the city, everything is within 15-20 minutes on foot.

Book Ahead

Book accommodation well ahead for summer and during the Palio races (July 2 and August 16). Reserve Palazzo Pubblico tower climbs and cathedral complex tickets online to avoid queues. Restaurant reservations recommended for dinner, especially on weekends.

Packing Essentials

Comfortable walking shoes with good support, layers for variable weather, sunscreen and hat, modest clothing for churches (covered shoulders and knees), refillable water bottle for public fountains, small daypack

Total Budget

$390-550 for three days (excluding accommodation and transportation to/from Siena)

Customize Your Trip

Budget Version

Stay in a hostel or agriturismo outside the walls with bus access. Focus on free attractions like churches and the Piazza del Campo. Skip tower climbs and paid museums, or visit on free entry days. Eat picnic lunches from markets and bakeries. Enjoy aperitivo hour when snacks come free with drinks. Shop at local supermarkets for breakfast supplies. Many city views are free from public spaces along the walls.

Luxury Upgrade

Book a five-star hotel in a restored palazzo with spa facilities. Arrange private guided tours of the cathedral and museums with art historians. Take a chauffeured day trip to nearby Chianti wineries or Montalcino for wine tastings. Dine at Michelin-starred restaurants. Enjoy cooking classes with local chefs. Book a private Palio museum tour to learn about the legendary horse race traditions. Consider helicopter tours of the Tuscan countryside.

Family-Friendly

Stay in a spacious apartment rental with kitchen facilities. Break up museum visits with gelato stops and playground time in park areas. The Musei dell'Accademia dei Fisiocritici natural history museum appeals to kids. Let children climb the tower at Palazzo Pubblico for adventure. Pack snacks and plan shorter morning sessions. Many restaurants welcome families early in the evening. Consider a countryside agriturismo where kids can see farm animals.

Book Activities for Your Trip

Tours, tickets, and experiences in Siena

Continue Planning Your Trip

Things to Do

Top attractions and activities for Siena

Budget Guide

Trip costs and money tips for Siena

Getting Around

Transport options and tips for Siena

Where to Stay

Accommodation guide for Siena

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