In Palestinian-controlled Bethlehem, the dwindling numbers of Arab Christians -- some call it an exodus -- will be on the pope's agenda as, of course, will be the Israeli-Palestinian conflict.
It is an unavoidable subject and Benedict has already said he is coming with messages of peace and justice, but every word he utters about the need for the two-state solution will be minutely scrutinized by Palestinians and the new right-wing Israeli government.
He will also visit a Palestinian refugee camp in the shadow of Israel's much-hated security barrier. It is a high concrete wall here and the symbolism will be too obvious to ignore.
There's no plan to go to Gaza, with memories of the fighting earlier this year and the loss of civilian life still fresh in the mind. Gaza's several thousand strong Christian community is the region's smallest and most vulnerable, occasionally under attack from Islamic extremists. Israel may give out 250 travel permits for Gaza's Christians to attend mass with the pope, but it hasn't happened yet.
There are many challenges facing the 82-year-old pope; this is his first trip to the Holy Land as pope, and almost certainly his last. He doesn't have the rock star qualities of his predecessor John Paul, who was a big hit here in 2000.
This is a minefield of sensitivities and for a pope with a habit of saying the wrong thing, leaving without causing a controversy may be enough of an achievement.