In the central Piazza Garibaldi, you'll find the Collegiate Church of San Martino that dates back to 1588. Here you'll find the Madonna and Child and the Saints by Sodoma; the Church of the Madonna delle Nevi with the neo-Gothic style gate and the Church of Santa Croce which preserves the altar table depicting the Marriage of the Virgin, by the school of Luca Signorelli, considered one of the greatest interpreters of Renaissance painting.
Palazzo Pretorio in Piazza IV Novembre has watched over the village since the Middle Ages. Built between 1337 and 1346, on the main facade and on the eastern side it houses various coats of arms of the Podestà from the time of the Republic of Siena and those of the Medici era. In particular, on the right side of the main portal there's a pillory where criminals or alleged criminals were placed to be publically mocked.
In the historic center, you can also visit the museum space dedicated to the Etruscans: "Le Stanze di Larth". Here, there are Etruscan finds from the necropolis of San Giustino and from the nearby Etruscan Le Carceri settlement, both of which are in the municipal area.
At the entrance to the town of Sinalunga is the Fonte del Castagno: an inscription dates the monument to 1265. The nearby underground passages form the Sentiero dell'Acqua, which can be visited by booking at the municipal tourist office.
The Church of San Bernardino in Poggio Baldino, dating back to 1449, is also worth visiting. It's adjoined to a convent of the Frati Minori order, which houses the Madonna del Rifugio icon and the Cristo Benedicente, both attributed to the early Italian Renaissance painter and illuminator, Sano di Pietro. It's also home to L'Annunciazione di Benvenuto di Giovanni (1470), and the Baptism of Christ and the Coronation of the Virgin and Child between Saints Simon and Taddeo (1483) by Guiduccio Cozzarelli.