I think this video of Holy Land topography very helpful. It keys off a book, Satellite Bible Atlas.
Here are other excellent map-based teaching videos:
01 Introduction. Land of the Bible: Location and Land Bridge (5 min)
02 Land of the Bible: Basic Regions and Regional Variety (10 min)
03 Major Routes in the Land of the Bible (6 min)
04 Approaches to Jerusalem and the Benjamin Region, Maps 1-8 and 1-9 (12 min)
05 Southern Approaches to Jerusalem, Map 1-8 (10 min)
06 Jezreel Valley and Lower Galilee, Map 1-4 (14 min)
07 Shephelah of Judah, Maps 1-10, 1-11 (12 min)
08 Samaria, Map 1-7 (15 min)
09 Jerusalem Highway (Modern) in Judean Hill Country (6 min)