The paper explores the potential of the application of Space Syntax methodology to Landscape Architecture. Dealing with the landscape architectural design process of an Urban Park as a case study, intensive use of DepthSpace3D, a software for 3D Space Syntax analysis, led to: a) a better understanding of the relations between the urban space shapes (spatial configuration, visibility and accessibility) and functions (physical, social and psychic); b) the implementation of an iterative process of project improvement, optimizing the fulfilment of the desired (by the landscape architect) character of the Urban Park, through mastered changes in ground shaping and selection of the species and spatial distribution of trees and shrubs; c) the improvement and suiting of DepthSpace3D to the special requirements of Landscape Architecture to Space Syntax digital tools. A deep research was endeavoured regarding the digital modelling of the vegetation: form and dimension, growth speed and visual permeability (transparency/opacity) of the crown in winter and summer.