Microwave (MW) drying of wood has gained popularity in the field of wood modification. The rise in temperature during MW drying leads to increased steam pressure, enhancing wood permeability but potentially decreasing mechanical properties. Understanding temperature and moisture behaviors during MW drying is crucial for its industrial application in wood drying. Therefore, this study aimed to characterize the temperature and moisture behaviors during MW drying of small Portuguese maritime pine (Pinus pinaster Aiton.) wood samples to support a wider use of this technology. The effects on water uptake and the compressive strength parallel to the grain were also investigated. The results indicated three distinct phases in the MW drying rates, with an average of 0.085% of water removed per second. Moreover, the temperature underwent three distinct stages: an initial rapid increase, a period of constant temperature, and a slight decrease until drying was complete. At the beginning of MW drying, the temperatures were below 100 °C, with average temperatures ranging from 126 to 145 °C. Specimens with lower initial moisture content had higher temperatures, and a positive correlation was found between initial moisture content and drying time. In contrast, negative correlations were found between the initial moisture content and average temperature, as well as average temperature and MW drying time. Additionally, the operating condition parameters used in MW drying of pine samples enhanced water impregnability by 65%, generating a slight reduction of 11% in compressive strength. It was also noticed that the initial moisture content did not impact MW-dried samples’ water uptake or compressive strength. Finally, although small clear wood samples of maritime pine were utilized, the temperature and moisture patterns observed closely matched real-scale specimens. Thus, the findings corroborate a wide utilization of MW technology for wood drying, mainly demonstrating positive possibilities for structural-sized wood specimens.