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Two days through the southern Marche with a guide who lives here: from Macerata, between the Sferisterio and the Loggia dei Mercanti, you head down into the Roman Cisterns of Fermo and stroll across the travertine square of Ascoli Piceno. Along the way, stops at Fiastra Abbey and the Roman ruins of Urbs Salvia, plus dinner at a farmhouse with a Piceno wine tasting. A slow route through history, hill towns and honest local flavours.