Sienna Italy 5 Day Itinerary

Day 1: Arrival & Exploring the Historic Center

  • Accommodation: Consider staying in a historic palazzo or a charming agriturismo near Siena. Some popular options include Palazzo Ravizzieri, Residenza d’Epoca La Cittadella, and Agriturismo Pieve di Mercatale.

  • Activities: Begin your day with a visit to the Piazza del Campo, the heart of Siena. Don’t miss the Palazzo Pubblico and its tower Torre del Mangia for panoramic views of the city.

  • Lunch: Head to Trattoria La Taverna dei Gamberi Rossi or Da Carmelo in the historic center for traditional Tuscan dishes.

  • Afternoon: Visit the Duomo di Siena, a masterpiece of Gothic architecture, and the Baptistery of San Giovanni. If you’re interested in art, the Museo dell’Opera Metropolitana is worth a visit.

  • Dinner: Dine at Trattoria La Chiostrina, located inside the Augustinian Monastery of Santa Chiara, or Osteria Le Logge, housed in the beautiful Logge del Papa.

  • Things to Know: Siena is famous for its white truffles. If you’re visiting between October and December, consider trying a white truffle meal. Also, remember that Siena has pedestrian-only zones, so double-check your route before driving.

Day 2: Day Trip to San Gimignano

  • Transportation: Take a train from Siena to San Gimignano (approximately 30 minutes). Alternatively, you can rent a car or join a guided tour.

  • Activities: Explore the medieval hill town of San Gimignano, known for its towers and Vernaccia wine. Visit the Collegiate Church of Santa Maria Assunta and the Rocca di San Gimignano.

  • Lunch: Enjoy a meal at Trattoria Vecchia Arbia or La Cantina de’ Nobili, both offering authentic Tuscan cuisine.

  • Afternoon: Continue exploring San Gimignano, browse the local shops for souvenirs, or visit the Museum of the Torture if you’re interested in a darker side of history.

  • Return to Siena: Spend the evening at leisure in Siena. Consider revisiting the Piazza del Campo during sunset for a stunning view.

Day 3: Day Trip to Montepulciano & Pienza

  • Transportation: Rent a car or join a guided tour to visit these charming hill towns.

  • Activities: Start in Montepulciano, known for its Vino Nobile di Montepulciano wine. Visit the Piazza Grande, the Palazzo Comunale, and the Church of San Biagio.

  • Lunch: Savor a meal at La Buca delle Fate or Locanda della Corte.

  • Afternoon: Continue to Pienza, the “ideal city” designed by Pope Pius II. Visit the Duomo di Pienza and the Palazzo Piccolomini. Don’t forget to try some Pecorino cheese, a local specialty.

  • Return to Siena: Spend the evening at leisure in Siena.

Day 4: Day Trip to Chianti Classico

  • Transportation: Rent a car or join a guided tour to explore the Chianti Classico region.

  • Activities: Visit some of the famous wine estates, such as Castello di Ama, Castello di Brolio, and Castello di Gabbiano. Enjoy wine tastings and learn about the region’s winemaking history.

  • Lunch: Have lunch at a local enoteca or trattoria, like Osteria Le Piazze in Radda in Chianti.

  • Afternoon: Continue exploring the beautiful landscapes of Chianti Classico, stopping at picturesque villages like Greve in Chianti and Castellina in Chianti.

  • Return to Siena: Spend the evening at leisure in Siena.

Day 5: Departure

  • Breakfast: Enjoy your final Tuscan breakfast at your accommodation before checking out.

  • Transportation: If you’re heading to the airport, consider taking a train from Siena to Florence (approximately 1 hour) and then a flight from Florence Airport (FLR). Alternatively, you can arrange for a private transfer or rent a car for your journey.