Volterra (Central Italy) is a town of great historical interest, due to its vast and well-preserved cultural heritage, including a 2.6 km long Etruscan-medieval wall enclosure representing one of the most important elements. Volterra is located on a clayey hilltop prone to landsliding, soil erosion, therefore the town is subject to structural deterioration. During 2014, two impressive collapses occurred on the wall enclosure in the southwestern urban sector. Following these events, a monitoring campaign was carried out by means of remote sensing techniques, such as space-borne (PS-InSAR) and ground-based (GB-InSAR) radar interferometry, in order to analyze the displacements occurring both in the urban area and the surrounding slopes, and therefore to detect possible critical sectors with respect to instability phenomena. Infrared thermography (IRT) was also applied with the aim of detecting possible criticalities on the wall-enclosure, with special regards to moisture and seepage areas. PS-InSAR data allowed a stability back-monitoring on the area, revealing 19 active clusters displaying ground velocity higher than 10 mm/year in the period 2011-2015. The GB-InSAR system detected an acceleration up to 1.7 mm/h in near-real time as the March 2014 failure precursor. The IRT technique, employed on a double survey campaign, in both dry and rainy conditions, permitted to acquire 65 thermograms covering 23 sectors of the town wall, highlighting four thermal anomalies. The outcomes of this work demonstrate the usefulness of different remote sensing technologies for deriving information in risk prevention and management, and the importance of choosing the appropriate technology depending on the target, time sampling and investigation scale. In this paper, the use of a multi-platform remote sensing system permitted technical support of the local authorities and conservators, providing a comprehensive overview of the Volterra site, its cultural heritage and landscape, both in near-real time and back-analysis and at different scales of investigation.