Siena Itinerary: 3 Days

ancient architecture basilica of san domenico building

Things to Do in Siena

Here’s a suggested Siena itinerary for spending 3 days in this beautiful town, including a wine tour in the nearby region:

Day 1

  • Morning: Start your day by exploring the historic center of Siena. Visit the stunning Siena Cathedral (Duomo di Siena) and marvel at its impressive architecture. Climb the Torre del Mangia for panoramic views of the city.
  • Afternoon: Take a leisurely stroll through Piazza del Campo, the main square of Siena, known for its unique shell-shaped design. Visit the Palazzo Pubblico and the Civic Museum, which houses important artworks, including the famous frescoes by Ambrogio Lorenzetti.
  • Evening: Enjoy a traditional Tuscan dinner at one of the local trattorias in Siena, savoring delicious regional specialties like pici pasta and bistecca alla fiorentina.

Day 2

  • Morning: Embark on a day trip to the Chianti wine region, located just outside Siena. Explore the picturesque countryside, characterized by rolling hills, vineyards, and charming villages. Visit a local winery and indulge in wine tasting sessions, learning about the winemaking process and the different varieties produced in the region.
  • Afternoon: Continue your exploration of the Chianti region by visiting the town of Greve in Chianti. Wander through its quaint streets, browse local shops, and perhaps sample some more wines at one of the enotecas (wine bars) in the area.
  • Evening: Return to Siena and enjoy a relaxed evening in the city. You can explore the local enotecas and wine bars, sampling different Tuscan wines or opt for a cozy dinner at a trattoria.

Day 3

  • Morning: Discover the artistic treasures of Siena by visiting the Pinacoteca Nazionale, a renowned art museum featuring an impressive collection of Sienese paintings from the 13th to the 18th centuries. Don’t miss the works of famous artists like Duccio di Buoninsegna and Simone Martini.
  • Afternoon: Immerse yourself in the medieval history of Siena by visiting the Museo Civico and the Torre del Mangia. Explore the narrow streets of the city, shop for souvenirs, or relax at a cafĂ©.
  • Evening: Indulge in a farewell dinner at a traditional Sienese restaurant, enjoying the local cuisine and perhaps pairing your meal with more Tuscan wines.

For the wine tour, the Chianti region is a great choice, known for its exceptional wines. There are several wineries in the area that offer tours and tastings. Some notable wineries include Castello di Ama, Castello di Brolio, and Badia a Coltibuono. Make sure to book your wine tour in advance to secure your spot and check for any specific requirements or recommendations from the wineries.

For an overview of all the Tuscany Winery Regions check out our blog HERE

Check out some Tours in Siena

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