Charles Ellicott Commentary Deuteronomy 1:7

"turn you, and take your journey, and go to the hill-country of the Amorites, and unto all [the places] nigh thereunto, in the Arabah, in the hill-country, and in the lowland, and in the South, and by the sea-shore, the land of the Canaanites, and Lebanon, as far as the great river, the river Euphrates." — Deuteronomy 1:7 (ASV)

Enter the mount of the Amorites — that is, the southern part of Judah, from which the five kings of the Amorites, the southern confederacy of Joshua 10 (see this chapter), arose to attack Gibeon. Israel would have marched into the heart of this territory had they entered from Kadesh, “by the way of the spies.”

And unto all the places near to it. —The rest of the promised land is thus described: In the plain —of Jordan. In the mountain —the hill-country of Judah in the south, Mount Ephraim in the centre, and the mountainous district further north. In the Shephêlah —Philistia. In the Negeb —the land afterwards assigned to Simeon, in the far south of Judah. And by the sea side to the north of Carmel (Judges 5:17), the coasts of the Great Sea over against Lebanon, and in the territory of Asher and Zebulun, as far as Phoenicia (Genesis 49:13).

The land of the Canaanites, and unto Lebanon. —The Canaanites held the plain of Esdraelon and the fortresses in the north. From Lebanon, the conquest would extend ultimately to the north-east, even to the great river, the river Euphrates.