As you wander through the cobbled streets of San Gimignano, there’s one spot you can’t miss: the Torre Grossa. Rising 54 meters, it’s the tallest tower in the city and has stood as a symbol of power and wealth since the 14th century. The climb—218 steps, no elevator—may be challenging, but the reward is a stunning 360-degree view of Tuscany’s rolling vineyards and the sea of terracotta rooftops below.

The Collegiata di Santa Maria Assunta or Duomo di San Gimignano is a Roman Catholic collegiate church and minor basilica in San Gimignano, in Tuscany in central Italy. It contains important cycles of Renaissance frescoes by artists including Domenico Ghirlandaio, Benozzo Gozzoli, Taddeo di Bartolo, Lippo Memmi and Bartolo di Fredi. It falls within the UNESCO World Heritage Site of the Historic Centre of San Gimignano, with its frescoes being described by UNESCO as works of outstanding beauty.

The chiesa di Sant'Agostino is the second largest church in San Gimignano, Italy, after the Collegiata. It is owned by the Order of Saint Augustine. Sant'Agostino is an imposing 13th century building. The interior is a large hall dominated by the seventeen-panel fresco cycle on The Life of St Augustine around the high altar, painted by Benozzo Gozzoli between 1463 and 1467. The altarpiece is the Coronation of the Virgin by Piero del Pollaiuolo. There are a number of other frescoes in the church. The Cappella di San Bartolo houses the remains of the eponymous saint, a lay Franciscan who died of leprosy. The magnificent altar in the chapel is by Benedetto da Maiano.

The Palazzo Comunale, also known as the Palazzo del Popolo of San Gimignano has been the seat of the civic authority in the comune since the 13th century. It is located on the Piazza del Duomo close to the Collegiate Church of the Assumption of the Blessed Virgin Mary. The building and Collegiate Church are at the heart of the medieval town, and are part of the UNESCO World Heritage Site of the Historic Centre of San Gimignano. The building contains important fresco decorations by Memmo di Filippuccio, Lippo Memmi and others, a museum and a gallery with works of the Florentine and Sienese schools of art - including paintings by Coppo di Marcovaldo, Lippo Memmi, Benozzo Gozzoli, Filippino Lippi, Il Sodoma and Pinturicchio.

Piazza della Cisterna is a piazza in San Gimignano, Italy. It has a triangular shape with a slight natural slope and is connected to the nearby Piazza del Duomo by an open passage. The pavement is brick and the piazza is surrounded by houses and medieval towers. There are presently 5 towers onto the square or very near it and the bases of other five are visible on the facade of the various palaces, plus one, the Ridolfi tower, which is no longer in existence having collapsed in 1646 onto the family palace, which divided the square in two alongside the short axis, thus making this relatively small area a concentrate of medieval architecture. In the south-west corner, the piazza meets the Arc of Becci,, an ancient city gate. The arc is flanked by the massive rectangular towers of Becci on the left and Cugnanesi on the right. Past the access to via di Castello on the east side, which led down to the original Bishop’s castle, the northern side of the square is occupied by the renaissance Cortesi Palace, which extended up to the torre del Diavolo, and extends along the north side of the square including the old houses of the Cattani family. The remains of two pre-existing towers of the Cattani palace are clearly visible onto the facade of the Cortesi Palace. The west side is adorned with various towers, like the twin towers of Ardinghelli and the tower of palazzo Pellari visible over the roofs.

The Saint Fina Chapel is an Early Renaissance chapel in the right aisle of the Collegiate church of Santa Maria Assunta, located in San Gimignano, Tuscany, Italy. It was designed by Giuliano and Benedetto da Maiano in 1468 to enshrine the relics of Saint Fina. The side walls of the chapel are painted in fresco by Domenico Ghirlandaio with two scenes from her life, executed between 1477 and 1478.

Piazza del Duomo is a city square in San Gimignano, Italy.

SanGimignano1300 is an artistic and historical museum located in the old city of San Gimignano. The museum was inaugurated in February 2010.