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Most Famous Guest: Cosimo de’ Medici. Castello di Montegufoni near Monttagnana Val di Pesa, Chianti, is just 20 km southwest of Florence and boasts an extremely illustrious history going all the way back to the 12th century (though the present castle structure mainly dates to the mid-17th). It has connections to Dante’s Divine Comedy and the infamous Medici dynasty of Florence for example, and has been steeped in art and politics since its very beginnings. It is thus a very interesting place, with such a noble history granting it a special atmosphere. It is also quite a quirky place to stay, one which seems to deliberately avoid creating a hotel-like vibe. This may not be to the liking of some, as there is less in the way of services and facilities but others will revel in the feeling of living in a castle as opposed to staying in a (castle) hotel. Of note in historical and artistic trivia; the owner of Montegufoni, Sir George Sitwell, in 1922 reneged on an arrangement made with Picasso for him to come and paint the frescoes at Montegufoni. The Italian futurist painter Gino Severini was chosen instead, with some very fine results, though many people READ MORE