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Pontassieve contains the remains of the medieval fortification and the three main gateways to the city: particularly significant is the Porta Aretina (Aretina Gateway Clock Tower), beyond which the old town developed that, flanking the Sieve river, meets the Medicean Bridge, constructed in 1555 by request of Cosimo I de' Medici. Of notable interest are the Palazzo Sansoni- Trombetta and the Filicaia Tower which belonged to the noblemen from Quona.
Recommended points of interest in Pontassieve: the romanesque Parish Church of St. Giovanni Battista a Remole placed in the centre of the inhabited area of Sieci, Trebbiano Castle, Torre a Decima Castle in Molin del Piano and the Sanctuary of Madonna delle Grazie del Sasso, in the vicinity of Santa Brigida.
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