Siena 2 Day Itinerary

Day 1: Exploring the Heart of Siena

Morning:

  • Arrival in Siena. If you’re arriving by train, the main station is Stazione di Siena. From here, you can easily reach the city center by bus (ARPAs line number 5 or 6) or a short taxi ride.

  • Start your day with a hearty Italian breakfast at La Casa del Brusciamele, Via Banchi 13r - a cozy café known for its homemade pastries and local honey.

  • Visit the Piazza del Campo - the iconic shell-shaped square and the heart of Siena. The Palazzo Pubblico, Torre del Mangia, and the Fonte Gaia are must-sees here.

  • Take a guided tour of the Palazzo Pubblico to admire the stunning frescoes by Simone Martini and Ambrogio Lorenzetti in the Salone dei Nove and Salone della Priora.

Afternoon:

  • Explore the Cattedrale di Santa Maria Assunta and its adjacent Baptistery, admiring the unique black-and-white striped marble facade.

  • Wander through the narrow, medieval streets of the city, such as Via di Città or Borgo Malvegiana, where you can find many artisan shops and small boutiques.

  • For lunch, head to Trattoria La Taverna dei Lupi, Via di Città 23r - a popular spot for locals serving traditional Tuscan dishes like pappardelle al cinghiale or ribollita.

Evening:

  • Relax at the Piazza San Domenico, home to the Basilica di San Domenico and the National Museum of the Opera Metzler, which houses some important artworks from the Sienese School.

  • Have dinner at Osteria Le Logge, Piazza del Duomo 9r - a high-end restaurant with an elegant terrace overlooking the cathedral.

Day 2: Countryside and Wine Tasting

Morning:

  • After breakfast, take a short train ride to Monteriggioni, a well-preserved medieval walled town just 20 minutes away from Siena. Explore the town’s circular layout and its four main gates.

  • Head to the Chianti region for a wine tasting experience. You can reach some wineries by bus (e.g., Castello di Brolio, Castellare di Castagnoli), or book a guided tour that includes transportation and tastings (e.g., Chianti Classico Wine Tours).

Afternoon:

  • For lunch, enjoy traditional Tuscan cuisine at a local winery restaurant or pack a picnic to enjoy amidst the vineyards.

  • In the afternoon, you can opt for more wine tastings, visit some of the beautiful hilltop towns like Radda in Chianti or Gaiole in Chianti, or simply relax and soak up the stunning Tuscan countryside views.

Evening:

  • Return to Siena and have dinner at Enoteca La Sant’Anna, Via di Sant’Antonio 28r - a charming wine bar offering an extensive selection of wines, cheeses, and charcuterie.

  • End your day with a stroll through the illuminated Piazza del Campo, taking in the magical atmosphere as the city comes alive at night.

Things to Know:

  • Siena can get very crowded during the Palio horse race (usually held twice a year in July and August), so it’s best to avoid these dates if possible.

  • Most shops and restaurants close on Sundays, so plan accordingly.

  • Taxis are relatively expensive in Siena, so consider using public transportation or walking whenever possible.

  • Purchase the Siena Card for discounted admission to museums and attractions.