Background/Objectives: Spheno-orbital meningiomas (SOMs) are rare tumors described as benign despite their aggressive, osteodestructive behavior. Their invasive nature makes surgical management complex and often precludes complete excision. Reaching structures within the orbit remains challenging, particularly due to insufficient exposure or overly long surgical pathways. This study aimed to provide a qualitative anatomical description of two approaches—transcranial and endoscopic transorbital—and a preliminary quantitative analysis to assess the distances required to reach the anatomical areas most commonly involved in SOMs. Methods: Anatomical dissections were performed on five specimens (ten sides) at the Laboratory of Surgical Neuroanatomy (LSNA), University of Barcelona. Each specimen underwent pre- and post-dissection CT scans, and all data were organized using the BrainLab^® Workstation System. Results: Both approaches provided good exposure of structures deeply involved in SOMs. A description of the superior orbital fissure (SOF), inferior orbital fissure (IOF), and optic canal (OC) was achieved from both perspectives. The preliminary quantitative analysis showed significantly shorter distances to key anatomical targets using the endoscopic transorbital approach (ETOA) compared to the transcranial route. Conclusions: Currently, despite significant advances, the choice of the optimal surgical approach remains debated, reflecting the complexity of balancing tumor control with functional preservation. Both approaches allow for thorough evaluation of the orbital region, offering precise anatomical insights useful for SOM management.