We use new structural and apatite fission-track data together with apatite fission-track and (U-Th)/He data from literature to examine the tectonic evolution of the continental Upper Valdarno Basin, in the hinterland sector of the Northern Apennines fold-and-thrust belt. This basin is located in-between two structural ridges, the Chianti Mountains to the southwest and the Pratomagno to the northeast. In our interpretation, the Upper Valdarno Basin developed at ca. 3.4-3.3 Ma as pop-down synformal-shaped depression bounded and controlled by oppositely-verging thrust-related structures, namely the thrust system lifting the Chianti Mountains and the southwest-facing backfolds at the base of the Pratomagno. This evolution is compatible with the accelerated exhumation rates at 4-5 Ma documented through apatite fission-track data along both the Pratomagno and Chianti ridges. Shortening suffered by basin deposits is clearly manifested by the outcrop-scale reverse faults and thrust-related folds affecting the Late Pliocene sediments (Castelnuovo dei Sabbioni Synthem), which are well exposed in the Santa Barbara mine. These strongly folded deposits are overlain unconformable by Early Pleistocene sediments (Montevarchi Synthem), which display evidence for syn-depositional normal faulting. This suggests that the Upper Valdarno Basin experienced a phase of normal faulting that started at the base of Pleistocene (ca. 2.6-2.5 Ma) and likely produced the large southwest-dipping “Trappola Fault”, which affects the southwestern margin of the Pratomagno displacing the earlier backthrusts and backfolds. Basin evolution can be thus basically framed into a two-phase history, with extensional tectonics superposed onto compressional structures that were deactivated by ca. 2.7 Ma. Being the Chianti Mountains part of the 250 km-long regional line of thrusts and thrust-related folds (the so-called “Tuscan Nappe front”), the results of this study may also involve regional implications, as they would also hint for the tectonic history of other sectors and basins settled along-strike this regional element.