Siena 5 Day Itinerary

Here’s a 5-day itinerary for traveling in Siena:

Day 1: Arrival and Exploring the City Centre

Places to Go:

  • Piazza del Campo: The heart of Siena is known as one of Europe’s greatest medieval squares. It hosts two palaces, the Torre del Mangia, and the Palazzo Pubblico.
  • Duomo di Siena (Siena Cathedral): A masterpiece of Romanesque architecture built on a hilltop offering panoramic views over the city.

Activities:

  • Explore the narrow streets around the square.
  • Visit the Pinacoteca Nazionale to see works by medieval artists.

Where to Eat:

  • La Taverna di San Giuseppe: For traditional Sienese dishes in a cozy, family-run atmosphere. Try their ribollita and pappardelle.

Where to Stay:

  • Hotel Reale or Hotel La Fonte, both are centrally located, offering comfortable rooms with a view of the city or the countryside.

Things to Know:

  • Siena is known for its strong medieval traditions; dress modestly when visiting churches.
  • Respect the local environment and traditions.

Transportation:

  • Walking: The best way to explore the city centre is on foot. Siena is relatively small, making walking not only efficient but also the best way to soak in the atmosphere.
  • Bus: For areas outside of the historic centre or for longer trips, buses are convenient and frequent.

Day 2: Countryside and Wine

Places to Go:

  • Chianti Wine Region: Visit a wine farm (enoteca) in the Chianti region. Enjoy wine tasting and learn about the production process.
  • Castello di Casigliano: For its castle, vineyards, and a winery that offers wine tastings.

Activities:

  • Take a bike tour of the countryside to enjoy the views of rolling hills covered with olive groves and vineyards.

Where to Eat:

  • La Taverna dei Caracci: In San Giuseppe a Terzere. Offers traditional dishes in an old tavern atmosphere, try their wild boar ragù.

Transportation:

  • Car or Taxi: For visiting wineries outside Siena, driving is the best option.
  • Bike Rentals: Available for those who prefer a more active approach to exploring the Chianti region.

Day 3: Art and History

Places to Go:

  • Pinacoteca Nazionale (National Gallery): Located in the Palazzo Brancacci. It houses an impressive collection of medieval paintings.
  • Museo Civico (Civic Museum): For a broader view of Siena’s history, from pre-Roman to modern times.

Activities:

  • Take a guided tour that focuses on art and historical periods to deepen your understanding of the city’s past.
  • Explore the narrow streets where you can find artists at work or selling their latest pieces.

Where to Eat:

  • La Taverna del Leone: For traditional Tuscan dishes in a cozy, intimate setting. Their pasta is homemade, making it a must-try.

Day 4: Castles and Countryside

Places to Go:

  • Castello di Perignano: A medieval castle that can be visited, offering views of the surrounding countryside.
  • San Gimignano (town): Known for its skyline of high towers, it’s a bit farther but worth visiting.

Activities:

  • Take a hike in the beautiful Tuscan countryside to enjoy nature and perhaps stumble upon some hidden gems like a small winery or a local farm.

Where to Eat:

  • La Taverna della Rocca: For traditional dishes made from local ingredients. It has an atmosphere that is both rustic and welcoming.

Day 5: Markets and Views

Places to Go:

  • Mercato Coppo (Market): A place where locals buy fresh produce, cheese, and wine. Try some of the local specialties.
  • Torre del Mangia: For panoramic views over Siena from its top.

Activities:

  • Explore the markets for local products to take back home.
  • Take a leisurely walk around the city centre to soak in the atmosphere before departing.

Where to Eat:

  • La Taverna di San Giuseppe: For another taste of traditional Sienese cuisine, try their ribollita and pappardelle one last time.

Tips:

  • Be prepared for crowds during peak tourist season.
  • Respect local traditions and environment.
  • Try to learn a few Italian phrases like ‘grazie’ (thank you) or ‘per favore’ (please).
  • Enjoy the local wines, especially the Chianti Classico.
  • Don’t miss out on the opportunity to taste some of the local cheeses.

Transportation:

  • Train: For those not driving, trains are a convenient option for longer trips outside Siena.
  • Walking: The best way to explore the city centre and its many hidden corners.
  • Bus: For shorter trips within Siena or to areas that are not easily reachable by walking.

This itinerary provides a good balance of historical sites, art, wine, and the local culture. It’s designed to give you a comprehensive experience of what Siena has to offer, from its beautiful medieval architecture to its rolling countryside and delicious food. Enjoy your visit!