Certaldo: Medieval Castello and Tuscan Landscape

Certaldo combines a walled historic centre with a landscape of vineyards, olive groves and hills. In the Castello, you’ll find medieval streets, art and the history of Boccaccio; outside the centre, cultivated land and woodland shape the scenery. When planning your trip, you can therefore weigh whether cultural history or the rural surroundings should be the main focus.

The Castello and its history

Certaldo’s historic centre, also known as the Castello, is surrounded by walls. Three ancient gates provide tangible historical landmarks: Porta Alberti, Porta al Sole and Porta al Rivellino. The centre can be reached by funicular from Piazza Boccaccio. Palazzo Pretorio stands at the highest and oldest part of the hill in Certaldo Alto, at the intersection of the medieval streets Via Boccaccio and Via del Rivellino.

Frescoes and stone and glazed terracotta coats of arms have been preserved on the façade and inside Palazzo Pretorio. They represent the families of the vicars who governed Certaldo from the late Middle Ages until the Grand Duchy of Tuscany was established. The furnishings thus connect the history of governance with a specific building in the old town centre, offering a different perspective on the Castello from its gates and walls.

Boccaccio, art and sacred sites

Casa del Boccaccio is a house museum dedicated to the work and life of Giovanni Boccaccio. Chiesa dei Santi Jacopo e Filippo is also associated with the writer: his tomb is inside the church. The two sites offer different ways to connect with Boccaccio: one through his work and life, the other through his burial place.

The Museo di Arte Sacra was originally a 15th-century Augustinian monastery. It displays paintings dating from the 12th to the 16th century, including works by Cenni di Francesco di Ser Cenni, Ugolino di Nerio and Meliore. The wide span of dates and the named artists make the museum a distinct point of interest for travellers interested in sacred art.

Next to Palazzo Pretorio is an old, now deconsecrated church, where 15th- and 16th-century frescoes and sinopie have been preserved. The Tabernacolo dei Giustiziati dates to around 1464–65 and is attributed to Benozzo Gozzoli. Together with the palace and the Museo di Arte Sacra, these sites show that Certaldo’s art history is not confined to a single building.

Landscape and regional produce

Around Certaldo, vineyards and olive groves alternate with clay hills, rows of cypress trees, cultivated land and woodland. This mix gives the surroundings a different character from the compact historic centre. If you’d like to take in the Tuscan landscape as well as art and architecture during your trip, this contrast can help you decide what you’d like to focus on during your stay.

One agricultural product associated with the region is Cipolla di Certaldo: a local variety of red onion with a sweet, distinctive flavour. Its designated growing area includes the municipality of Certaldo and some neighbouring municipalities. This product adds a specific regional feature to the town’s architectural and artistic history, without implying that any particular tasting experience is available.

Events and planning your stay

Boccaccesca is a traditional food and wine event in Certaldo. Mercantia returns to Certaldo Alto; the 2026 edition is titled “Un’incessante Sinfonia”. If an event is important to your travel plans, check the dates in advance. This lets you choose your travel dates to suit your interests without assuming that the event titles amount to a complete programme.

When choosing accommodation, you can first consider which side of Certaldo you’d most like to experience: the Castello, with its historic sites and artworks, or the surrounding area, shaped by vineyards, olive groves and other landscapes. Literature, sacred art, architecture and regional produce offer different points of interest for travel groups with diverse interests. You don’t have to give every aspect equal weight; what matters is which themes you’d like to shape your stay.

Discover more destinations

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