Mapping forest disturbances is an essential component of forest monitoring systems both to support local decisions and for international reporting. Between the 28 and 29 October 2018, the VAIA storm hit the Northeast regions of Italy with wind gusts exceeding 200 km h−1. The forests in these regions have been seriously damaged. Over 490 Municipalities in six administrative Regions in Northern Italy registered forest damages caused by VAIA, that destroyed or intensely damaged forest stands spread over an area of 67,000 km2. The present work tested the use of two continuous change detection algorithms, i.e., the Bayesian estimator of abrupt change, seasonal change, and trend (BEAST) and the continuous change detection and classification (CCDC) to map and estimate forest windstorm damage area using a normalized burned ration (NBR) time series calculated on three years Sentinel-2 (S2) images collection (i.e., January 2017–October 2019). We analyzed the accuracy of the maps and the damaged forest area using a probability-based stratified estimation within 12 months after the storm with an independent validation dataset. The results showed that close to the storm (i.e., 1 to 6 months November 2018–March 2019) it is not possible to obtain accurate results independently of the algorithm used, while accurate results were observed between 7 and 12 months from the storm (i.e., May 2019–October 2019) in terms of Standard Error (SE), percentage SE (SE%), overall accuracy (OA), producer accuracy (PA), user accuracy (UA), and gmean for both BEAST and CCDC (SE < 3725.3 ha, SE% < 9.69, OA > 89.7, PA and UA > 0.87, gmean > 0.83).