Tags: travel

Siena, a city in Tuscany, central Italy, is the capital of the province of Siena. Traditionally spelled Sienna in English, it is the twelfth most populated city in the region, with a population of 52,991 as of 2025.

5-Day Itinerary: Siena + Hill Towns (July 6–10)

Sunday, July 6 – Siena & Cathedral Mass

Morning:

• Breakfast in Siena.
  
• 11:00 AM Mass at Siena Cathedral (Duomo) — Be there by 10:45 AM

Afternoon:

• Visit Duomo complex: Piccolomini Library, Crypt, and Baptistery.
  
• Stroll through Piazza del Campo & climb Torre del Mangia (400 steps).

Evening:

• Dinner at Osteria Permalico, Antica Osteria da Divo, Via Pantaneto, or Contrada dell’Oca.

Monday, July 7 – Monteriggioni & Castellina in Chianti

• 8:30 AM: Bus 130 to Monteriggioni (~30 min).
  
• 9:00–11:00 AM: Explore fortress walls, museum, coffee in Piazza Roma.
  
• 11:15 AM: Bus 125 to Castellina in Chianti (~1 hr).
  
• 12:15–4:30 PM:
  • Wine tastings at Taverna Squarcialupi, Tenuta Casanova, and stroll Via delle Volte.
    
• 4:30–6:00 PM: Return to Siena by bus.

Tuesday, July 8 – San Gimignano & Extended Volterra Visit

• 7:10 AM: Depart Siena (Bus 130) → San Gimignano (~1 hr).
  
• 8:10–12:00 PM: Explore towers, gelato, and artisan shops.
  
• 12:30 PM: Bus 31 to Volterra (~45 min).
  
• 1:15–5:15 PM:
  • Explore Volterra: Roman Theatre, Palazzo dei Priori, Etruscan Museum, late lunch.
    
• 5:15 PM: Bus 31 back to San Gimignano.
  
• 6:00–6:30 PM: Bus 130 to Siena (~1 hr).
  
• 7:30 PM: Return to Siena.

Wednesday, July 9 – Siena Market & Leisure

Morning:

• Visit Siena’s weekly market at Fortezza Medicea (open 7:00 AM–2:00 PM).

Afternoon:

• Relax at Orto de’ Pecci or visit Pinacoteca Nazionale.

Evening:

• Optional: Contrade museum visit or wine tasting in town.

Thursday, July 10 – Final Morning & Train to Bologna

Morning:

• Final coffee in Piazza del Campo or souvenir shopping.

Midday:

• Take the train Siena → Florence SMN → Bologna Centrale (~2.5–3 hrs).
  
• Suggested departure: 11:00 AM or 1:00 PM.