Ithilien and the Vale of Morgul
The trees growing along the slopes and bluffs of North Ithilien were mostly resinous: fir, cedar and cypress. (Of Herbs and Stewed Rabbit; Bk 2). The travellers were now some 500 miles south of Hobbiton, and the climate was distinctly warmer. The Vale of Anduin here was apparently more or less on two levels: the higher, which was heavily wooded and along which the road ran, and the lower fields by the river, which were less heavily wooded and very fertile, until devastated by Sauron. (The Council of Elrond; Bk 1; Of Herbs and Stewed Rabbit; Bk 2).
It was about 100 miles from Morannon to the Crossroads. On their second day going south, after passing through a deep cutting, they turned right, off the road, and came to a small lake. Henneth Annun, to which Faramir led them, was about 10 miles away and some 30 miles from the east bank of Anduin. It was also some 75 miles from Minas Tirith. (Of Herbs and Stewed Rabbit; The Window on the West: Bk 2; The Siege of Gondor; Bk 3).
After leaving Henneth Annun the Hobbits followed the sheer edge of the bluff south until the forest thinned out and they looked down into the Vale of Morgulduin. (Journey to the Crossroads; Bk 2). Thence they turned back into the forest, then east to hogsback and finally south to the Crossroads itself.
Going east up the Morgul valley they turned left just opposite the bridge to Minas Morgul, and climbed first the Straight Stair and then the Winding Stair up to the tunnel and Cirith Ungol. (The Stairs of Cirith Ungol; Bk 2).