Siena-4-day-itinerary

Day 1: Arrival and Exploration

Morning

  • Arrive in Siena and check-in at Hotel Palazzo Tolomei or similar
  • Start your day at Piazza del Campo, the heart of Siena’s historic center
    • Admire the stunning architecture and soak up the lively atmosphere
    • Visit the Palazzo Pubblico and climb the Torre del Mangia for breathtaking views

Afternoon

  • Explore the charming streets and alleys of Siena’s old town
    • Visit the Basilica di Santa Maria Assunta (Duomo) and admire its stunning Gothic architecture
    • Stop by the Museo dell’Opera Metropolitana to see works of art from the 12th to 19th centuries

Evening

  • Enjoy dinner at La Taverna di San Giuseppe, a cozy restaurant serving traditional Tuscan cuisine
    • Try their famous Pici all’Aglione (hand-rolled pasta with garlic and olive oil)
    • Don’t forget to order a glass of Chianti wine!

Things to Know

  • Siena is a pedestrian-friendly city, so be prepared to walk on cobblestone streets and climb stairs
  • The city has a rich history, so consider purchasing a guided tour or audio guide to get the most out of your visit

Transportation

  • From Florence: Take the bus (around 3 hours) or train (around 4 hours with changes) from Florence’s main stations
  • From Rome: Take the train (around 3.5 hours with changes) from Rome’s Termini station
  • Within Siena: Walk or take a taxi/ride-hailing service

Day 2: Wine and Countryside

Morning

  • Visit Castello di Brolio winery for a wine tasting and tour (book in advance)
    • Learn about the history of Chianti wine and enjoy the stunning views of the Tuscan countryside

Afternoon

  • Explore the picturesque village of San Gimignano (around 30 minutes by car or bus)
    • Admire the medieval towers and fortifications, and enjoy lunch at a local trattoria
    • Visit the nearby Villa La Pietra, a beautiful Renaissance villa with stunning gardens

Evening

  • Enjoy dinner at La Porta in Siena, known for its creative take on traditional Tuscan cuisine
    • Try their famous Pappardelle al Cinghiale (wild boar ragù) and finish with a Tiramisù dessert

Tips

  • Book your wine tasting and tours in advance to avoid long wait times
  • Consider renting a car or hiring a driver for the day to explore the countryside more easily

Transportation

  • From Siena: Take a bus (around 30 minutes) or drive (around 20-30 minutes) to San Gimignano
  • Within Siena: Walk, take a taxi/ride-hailing service, or use public transportation

Day 3: Art and Culture

Morning

  • Visit the Pinacoteca Nazionale di Siena to see an impressive collection of Tuscan art
    • Admire works by artists such as Duccio, Lorenzetti, and Sassetta

Afternoon

Evening

  • Enjoy dinner at Le Logge in Siena, offering creative takes on traditional Tuscan dishes
    • Try their famous Tagliatelle al Tartufo (truffle pasta) and finish with a Panna Cotta dessert

Things to Know

  • Many museums and attractions offer free admission on certain days of the week or month, so be sure to check before planning your itinerary
  • Siena is known for its contrade, 17 neighborhoods that compete in the Palio horse race; consider visiting one of the contrada museums to learn more

Transportation

  • Within Siena: Walk, take a taxi/ride-hailing service, or use public transportation

Day 4: Departure

Morning

  • Spend the morning shopping for souvenirs or exploring any last-minute sights

Afternoon

  • Depart for Florence, Rome, or other destinations in Tuscany

Tips

  • Be sure to try some of Siena’s famous sweets, such as Ricciarelli (almond biscuits) and Cantucci con Vin Santo (almond cookies with dessert wine)
  • Consider purchasing a Siena Tourist Card for discounts and free admission to various attractions