The Intended Route of Xanderian and Company

From Rivendell across the High Pass, south along the Anduin past the Gladden fields, then threading the needle between Lothlorien and Dol Guldur. Across the bridge at Parth Celebrant into the Wold, then south to Cliving, then Faldham. Into the Westfold, then back past Edoras, across the paths of the dead into Gondor.

Simple. What could possible go wrong?