Sienna, Italy 2 Day Itinerary

Day 1: Exploring the Medieval Charm of Siena

Morning:

  • Check-in at your accommodation. Some good options include Hotel Atlantea, Palazzo Ravizza, or Residenza Dama Fortuna for a mix of luxury and historic charm.

  • Start your day with breakfast at Picnic Siena, a charming café offering a variety of sweet and savory pastries.

  • Visit the Duomo di Siena (Siena Cathedral), a masterpiece of Gothic architecture adorned with intricate marble decorations. Don’t miss the famous Piccolomini Library and the mosaic floor.

  • Head to the Piazza del Campo, the heart of Siena, and one of Europe’s greatest medieval squares. Climb the 500 steps to the top of the Torre del Mangia for a panoramic view of the city.

Afternoon:

  • Lunch at Trattoria La Lupa, a family-run trattoria serving traditional Tuscan cuisine in a cozy, rustic setting.

  • Explore the Palazzo Pubblico and its adjacent museum, Pinacoteca Nazionale, home to many significant artworks, including masterpieces by Simone Martini and Ambrogio Lorenzetti.

  • Visit the Bapistry of San Giovanni and the Opera Metallica, a 14th-century work of art displaying the history of Siena in metal relief.

Evening:

  • Dinner at Osteria Le Logge, located in the beautiful Piazza del Duomo, offering refined Tuscan cuisine with a contemporary twist.

  • Stroll around the illuminated Piazza del Campo and enjoy the romantic atmosphere of Siena’s medieval city center.

Day 2: Countryside & Wine

Morning:

  • Breakfast at your accommodation or grab a quick bite at a local bakery.

  • Take a Chianti wine tour to explore the beautiful Tuscan countryside, visit historic vineyards, and enjoy wine tastings. Companies like Wine Check Siena offer guided tours and transfers.

Afternoon:

  • Lunch at a local winery or head back to Siena for lunch at Trattoria La Buca, serving delicious homemade pasta dishes.

  • Visit the Museo dell’Opera del Duomo to see more works of art from the cathedral, including Duccio’s Maesta and Donatello’s St. George.

Evening:

  • Dinner at Ristorante La Taverna, a cozy restaurant offering a wide selection of traditional dishes with a modern twist.

  • End your evening with a leisurely walk around the city center, taking in the illuminated beauty of Siena under the stars.

Things to Know:

  • Many shops and restaurants close between 1:00 PM and 4:00 PM for the “riposo.” Plan accordingly.
  • The best way to explore Siena is on foot, but consider renting a bike if you’d like to see more of the countryside.
  • English may not be widely spoken in some establishments, so learning a few Italian phrases can be helpful.
  • Remember to tip about 10% in restaurants and cafes.

Transportation:

  • Siena has an excellent public bus system, ATAF, that covers the city and nearby areas. Tickets can be purchased at tabacchi (tobacconists) or kiosks.
  • If you’re traveling to nearby cities like Florence or Rome, consider using trains operated by Trenitalia.