Morning: Arrive in Siena and settle into your hotel near the city walls. Take a leisurely walk to the iconic Piazza del Campo, where you can admire the medieval shell-shaped square and sip an espresso at a nearby café.
Afternoon: Explore the grand Siena Cathedral (Duomo di Siena), marveling at its striped façade and the intricate marble floor. Adjacent is the Piccolomini Library, housing stunning frescoes by Pinturicchio.
Evening: Climb the Torre del Mangia for panoramic sunset views over Tuscany. Enjoy a traditional Tuscan dinner in a trattoria overlooking the Piazza del Campo, sampling ribollita and local Chianti.
Find HotelsMorning: Visit the historic Palazzo Pubblico and its impressive Piccolomini Hall, home to the famous frescoes of the "Allegory of Good and Bad Government". Take a short stroll to the Santa Maria della Scala museum complex.
Afternoon: Wander through the winding streets of the Contrada neighborhoods, learning about Siena’s unique district traditions. Stop at the Church of San Domenico to see the relic of St. Catherine of Siena.
Evening: Join a local wine tasting tour in the nearby Chianti countryside, sampling renowned red wines and enjoying a light dinner of pecorino and cured meats under the stars.
Find HotelsMorning: Take a short bus ride to the medieval town of San Gimignano, famed for its towers and Vernaccia wine. Stroll the cobbled lanes and visit the Collegiata di Santa Maria Assunta to see its frescoed interior.
Afternoon: Return to Siena for a relaxing afternoon in the Orto de’ Pecci public garden, perfect for a picnic. Optionally, explore the National Museum of Siena for deeper insight into local art and history.
Evening: Conclude your trip with a farewell dinner at a rooftop restaurant overlooking the Piazza del Campo, enjoying live music and a final glass of Brunello di Montalcino.
Find HotelsIf you have an extra day, consider a full-day excursion to the rolling hills of Val d'Orcia, visiting Pienza and Montalcino for more cheese and wine experiences. To shorten the trip, skip the San Gimignano day trip and spend the afternoon exploring Siena’s artisan shops and local markets instead.