The exploration of the land marks a critical turning point in history, transforming a simple geographic mission into a fateful spiritual failure. The physical progression of the men masks a deeper internal dynamic and a severe moral shift.
The journey begins with the men turning and heading up the mountain. On a practical level, this physical movement directly follows Moses' command to ascend the mountain in the southern region [ספורנו, שפתי כהן]. However, this turning represents more than just a change in physical direction; it signifies a profound spiritual deviation. Before departing, the men were considered righteous, but the moment they turned to leave, they deviated from reason and began their descent into wickedness [אור החיים]. Alternatively, this turning describes the later stage of their journey as they prepared to return. Initially, fearing detection, the men toured the land as individuals. Only when they turned to head back did they finally regroup [מלבי״ם].
Their path eventually brought them to the Valley of Eshcol, located in the southern part of the land near the Israelite camp in Kadesh Barnea [ספורנו]. The primary approach among commentators is that the valley did not originally bear this name. Instead, it was named retroactively for the cluster of grapes the men would later cut from there on their return journey. This valley served as a central gathering point. While Caleb had traveled alone to Hebron [העמק דבר] and the others had surveyed different areas separately, they all reunited at Eshcol [מלבי״ם]. Gathering the fruit at this location signaled the conclusion of their espionage mission, as it would have been illogical to carry heavy fruit throughout their entire journey [ברכת אשר].
The nature of their task was fundamentally different from ordinary travel. The spying targeted the Land of Israel as a whole, rather than just the valley itself [ביאור שטיינזלץ, ברכת אשר]. While a typical traveler simply looks forward to reaching a destination, a spy meticulously examines every step to deeply understand the environment and its inhabitants [אור החיים, רש״ר הירש]. It was specifically at this reunion in the Valley of Eshcol that the men made a collective decision to act as spies intent on slandering the land. Instead of merely observing the land's goodness as originally intended, they actively sought out the weaknesses of the local nations [מלבי״ם].
Regarding their method of surveying, a prominent interpretive tradition suggests the men walked in a crisscross grid pattern, much like workers moving between rows in a vineyard [רש״י, מזרחי, חזקוני]. This thorough approach is hinted at by the sequence of their actions [ברכת אשר]. To explain how they managed this pattern while also inspecting the borders, commentators propose that they divided the roughly square land into four distinct quadrants, touring each one [גור אריה]. Another perspective suggests they walked along the outer borders on their way in, but chose more internal, intersecting paths for their return. This allowed them to thoroughly inspect the interior without arousing suspicion, naturally creating a crisscross route [משכיל לדוד, לבוש האורה].
Ultimately, their choice to walk the land physically carried lasting historical and spiritual consequences. Because the men abandoned the miraculous guidance of the Clouds of Glory and chose instead to inspect the land on their own feet, they established a permanent reality for future generations. From then on, the pilgrimage to the Temple during the three major festivals would always be performed by walking on foot [שפתי כהן].