Issachar's territory was fertile, but also a constant battleground. The Jezreel Valley, aka Megiddo, was on the border of Issachar and Manasseh, but mostly in Issachar.
Joshua 19:17-23

Asher occupied extensive territory on the Mediterranean, including the city of Tyre. They didn't keep it, unfortunately.
v24-31

Naphtali's territory was at the extreme north of Canaan. Until Dan relocated to the north, they were the northernmost tribe.
v32-39

Dan's territory was initially on the coast between Judah and Ephraim, but they were unable to hold out against the Philistines and many of them moved north of Naphtali, essentially creating a smaller colony north of the Sea of Galilee.
v40-48