Itinerary Suggestions: Siena

Time-Based Overviews

These structured itineraries assist in making the most of your time in Siena, whether for a brief stop or a longer stay.

They outline attractions and experiences suitable for various durations.

Flexible Planning

24-hour Layover Highlights
Weekend Getaway (2-3 days)
One-Week Comprehensive Experience

Detailed Timelines

Breakdowns for short visits, providing a guided approach to Siena's marvels.

-Hour Layover

A quick immersion in Siena's essence.

Morning to Evening

Morning: Arrive, Piazza del Campo.
Late Morning: Palazzo Pubblico, Torre del Mangia.
Lunch: Authentic Pici pasta.
Afternoon: Siena Duomo complex.

Book tickets for Duomo in advance. Enjoy aperitivo and Sienese specialties for dinner.

Weekend Getaway 2-3 Days

A more relaxed pace with exploration.

Day 1-3 Focus

Day 1: Piazza del Campo, Palazzo Pubblico, Torre del Mangia.
Day 2: Siena Duomo, cooking class or Monteriggioni trip.
Day 3: Fortezza Medicea, San Domenico Basilica, final lunch.

One-Week Comprehensive

Extensive city and countryside exploration.

Week's Activities

Days 1-3: Siena city exploration.
Days 4-5: Tuscan countryside, Chianti, Val d'Orcia.
Day 6: Florence or San Gimignano excursion.
Day 7: Relax, last-minute shopping, departure.

Two-Week In-Depth

A slower pace with cultural immersion.

Extended Immersion

More extensive hiking or cycling.
Visit more thermal baths (Saturnia, Bagni Vignoni).
Overnight at an agriturismo.
Consider renting a vacation apartment or villa.

Long-Term Stays

For stays longer than two weeks, consider a rental for a local experience.

More Space

Vacation apartment or villa for comfort.

Kitchen Access

Self-catering options for culinary adventures.

Local Life

Settle into Siena's rhythm, take classes.

Itinerary Flexibility

These itineraries are starting points; adapt them to your pace and interests.

Tailored Experiences

Align your itinerary with your specific passions, from history to culinary arts.

Historical & Heritage

Focus on Siena's rich past.

Historical Sites

Duomo complex (Cathedral, Museo dell'Opera, Baptistery).
Santa Maria della Scala, Pinacoteca Nazionale.
Palazzo Pubblico/Museo Civico.
Guided historical walking tours for contrade.

Visit San Domenico Basilica and the Sanctuary of Santa Caterina.

Food & Culinary

Indulge in Tuscan flavors.

Gastronomic Journey

Mercato Coperto for fresh local produce.
Hands-on Sienese cooking class (pici pasta).
Wine tours in Chianti, Montalcino, Montepulciano.
Food tours exploring local delis.

Adventure & Outdoor

Explore Tuscany's natural beauty actively.

Active Pursuits

Hiking or cycling routes in Tuscan countryside.
Hot air balloon ride for aerial views.
Walking sections of the Via Francigena.
Rent bikes (or e-bikes) for Chianti hills.

Enjoy the fresh air and stunning vistas of the region.

Family-Friendly

Activities for all ages.

Family Fun

Plenty of time in Piazza del Campo for play.
Climb Torre del Mangia (age permitting).
Frequent gelato stops.
Consider an agriturismo stay with a pool.

Art & Architecture

Dive into Siena's artistic heritage.

Artistic Exploration

Intensive exploration of the Duomo complex.
Pinacoteca Nazionale and Santa Maria della Scala.
Study frescoes in Palazzo Pubblico.
Guided tour focusing on Gothic architecture.

Spiritual & Wellness

A journey of tranquility and rejuvenation.

Peaceful Retreat

Sanctuary of Santa Caterina and San Domenico Basilica.
Thermal baths in Rapolano Terme, Bagni Vignoni.
Seek quiet corners for meditation.
Explore tranquil Abbazia di Sant'Antimo.

Personalized Journeys

These suggestions guide your Siena visit, aligning with your travel style and preferences.

Budget & Seasons

Practical considerations for budget-conscious travelers and seasonal highlights.

Backpacker's Guide

Maximizing Siena on a minimal budget.

Thrifty Travel

Hostel dorm or a budget B&B just outside the city walls.
Walk everywhere; local buses for longer distances.
Pizza slices, paninis, and picnic with groceries.
Prioritize free attractions (Piazza del Campo).

Mid-range Traveler

Comfort and immersive experiences.

Balanced Budget

Well-located B&B or a comfortable 3-star hotel.
Meals at local trattorias, occasional aperitivo.
Combined tickets for attractions.
Group walking or wine tours.

Luxury Experience

Premium services and exclusive access.

High-End Travel

5-star hotel or luxury villa/agriturismo.
Fine dining, private wine tastings, chef-led classes.
Private transfers and guided tours.
Attend the Palio with premier seating.

Value-Focused

Smart choices for maximizing your experience.

Smart Savings

Travel during shoulder or low season.
Utilize cumulative tickets for attractions.
Properties slightly outside the main tourist area.
Balance restaurant meals with self-catering.

Seasonal Highlights

Summer June-Aug

Outdoor dining, Palio (July 2, Aug 16). Expect crowds and heat.

Autumn Sept-Oct

Wine harvest festivals, truffle hunting. Duomo mosaic floor uncovered.

Winter Nov-Mar

Fewer crowds, cozy trattorias, Christmas markets in Dec.

Embrace Spontaneity

Regardless of your itinerary, allow time for unstructured wandering. Siena's charm unfolds with spontaneous discoveries and relaxed enjoyment.

Itinerary Suggestions