Forest mechanisation plays an important role in increasing labour productivity and reducing production costs. This work aims at evaluating various logging scenarios in Calabrian pine high forests, considering technical, economic and environmental aspects. The cut-to-length system was adopted and structured as follows: felling and processing operations were carried out using a medium-sized chainsaw while extraction of the processed material was carried out using three different vehicles for timber extraction: (i) by cable skidder, (ii) by grapple skidder and (iii) by a forwarder. The methodology was based on productivity analysis and production cost analysis, while for environmental performance, the life cycle assessment (LCA) approach was adopted. The selected functional unit (FU) was referred to as 1 h of logging operations. However, to assess the resulting usefulness, further analyses were performed using an alternative FU consisting of 1 m3 of round wood. The study’s outcomes show the complexity in achieving an optimal balance between productivity, economic aspects and sustainable management in forest operations.