Wildfires constitute the most important natural disturbance of Mediterranean forests, driving vegetation dynamics. Although Mediterranean species have developed ecological post-fire recovery strategies, the impacts of climate change and changes in fire regimes may endanger their resilience capacity. This study aims at assessing post-fire recovery dynamics at different stages in two large fires that occurred in Mediterranean pine forests (Spain) using temporal segmentation of the Landsat time series (1994–2018). Landsat-based detection of Trends in Disturbance and Recovery (LandTrendr) was used to derive trajectory metrics from Tasseled Cap Wetness (TCW), sensitive to canopy moisture and structure, and Tasseled Cap Angle (TCA), related to vegetation cover gradients. Different groups of post-fire trajectories were identified through K-means clustering of the Recovery Ratios (RR) from fitted trajectories: continuous recovery, continuous recovery with slope changes, continuous recovery stabilized and non-continuous recovery. The influence of pre-fire conditions, fire severity, topographic variables and post-fire climate on recovery rates for each recovery category at successional stages was analyzed through Geographically Weighted Regression (GWR). The modeling results indicated that pine forest recovery rates were highly sensitive to post-fire climate in the mid and long-term and to fire severity in the short-term, but less influenced by topographic conditions (adjusted R-squared ranged from 0.58 to 0.88 and from 0.54 to 0.93 for TCA and TCW, respectively). Recovery estimation was assessed through orthophotos, showing a high accuracy (Dice Coefficient ranged from 0.81 to 0.97 and from 0.74 to 0.96 for TCA and TCW, respectively). This study provides new insights into the post-fire recovery dynamics at successional stages and driving factors. The proposed method could be an approach to model the recovery for the Mediterranean areas and help managers in determining which areas may not be able to recover naturally.