An exemplar of the best of the Tuscan rural landscape, Montescudaio, is an incredibly beautiful village, and has in fact been awarded official recognition as such. There’s nothing quite like catching a stunning sunset from the historic castle walls, gazing out at the Tyrrhenian Sea and its islands. Wander down the cobbled, winding paths of the Medieval town, making sure to savour the scents of fresh bread baking in the wood ovens. Moving slightly outside to where the vineyards create their magic, you’ll find top-quality wines, with two that have been recognized as DOC (Controlled Denomination of Origin). The impressive castle, with its walls rising up to 15 meters, still features a watchtower, the Guardiola, dating back to the 12th century, that offers a breathtaking vista of the sweeping Cecina plain that reaches out to kiss the sea. You’ll also find the Scornabecchi Garden Park within close distance, and an archaeological area from the Middle Ages, that includes a historic convent. The district of Poggiarello is particularly intriguing, with houses leaning against each other and 17th-18th century buildings to be found in the historic center.