I think we should go with Erinhue's suggestion to head up river until we reach the juncture at the Field of Celebrant, and then take to land the rest of the way. Djaleh and the Eagle can scout ahead for us, but I don't think we need to mess with Mordor. At this time in the Third Age, its closeness to Gondor would have kept it a barren wasteland---nothing would be stupid enough to return quite yet. I'd say the real problem areas would probably be South (Harad), Far North (The Waste) and the East around Rhun, where any minions left from the war would have fled.
The nice thing about the East is that Tolkien wrote so little about it, that we really can use our imagination.
The only thing I ask is that no one finds Pallando or Tempest for awhile. I have thought out some of the plot strands related to them (don't worry, CR, we'll get Pallando eventually
) and I've figured out what happened to them both. I'll leave enough breadcrumbs so that your characters won't be totally frustrated in their search.....