Day Trip To Monticchiello

The month of November is one of the most tranquil, yet pleasant times to explore Tuscany. While the sun sets a little too soon, exploring towns not infiltrated by summer tourists is a good reason as any to visit during this time. Since we believe in highlighting lesser-known destinations, our day-trip suggestion for the month is a tiny town, called the ‘terrace of Val d’Orcia’ that many have never heard of. Nestled in the stunning and UNESCO-recognized Val d’Orcia which seems to burst with colors during the autumn months. While Pienza and Montepulciano are quite famous, Monticchiello is the humble little sister around 2 hours and 20 minutes from Villa Campestri. It’s no less pretty, but certainly less crowded.


The origins are said to be from the Roman times – with traces of the town existing from a document dating back to 973 where Lamberto Aldobrandeschi hands it to the Badia Amiatina. From the majestic countryside, the town itself is perched on a Sienese hill, with remains of an old castle and city walls of the ex-castle used to protect nearby Siena. During the mid-1200’s the city flourished but then later declined in the 1500’s. There were once over 17 towers, but like San Gimignano, only a few remain – the tallest is the privately owned Torre del Cassero.

Nowawadys, things are quiet and decidedly picturesque to the extreme. Entering from Porta Sant’Agata flanked by two defensive towers (one cut off), it is like entering another world. Houses in stone are lovingly kept up by their inhabitants, with plenty of flowers and adornments that almost feel like a Tuscan postcard, but in person. In the summer time, residents take part of the “Teatro Povero” a community theater that expresses their daily life and social situations, a comedic entry into Italian everyday life from July to August.

Attractions to visit are few, besides the town itself. They include 13th century The Church of Santi Leonardo e Cristoforo, home to a Madonna by artist Pietro Lorenzetti and beautiful frescoes. We recommend planning lunch or dinner, and having a walk along the quiet streets. Locals are friendly and don’t be shy to say ‘Buongiorno’ when passing by.

There are two restaurants in the town center, one is the excellent “Osteria La Porta”, which offers a nice view during the summer months (ask for a table on the terrace) otherwise you can go for a more low-key dinner at the rustic “La Taverna di Moranda”. This is the territory of wild boar, so go for a freshly made pasta of ‘cinghiale’ or rabbit, starting with a meat and cheese platter with cinta senese salami. Nearby notable places include Terre di Nano and La Guardiola.

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