By Daniel Burke, CNN Belief Blog Editor

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(CNN) - So, a rabbi, a sheikh and a pope travel to the Holy Land…

It might sound like the start of a trite joke, but it’s actually the entourage for one of the most highly anticipated papal trips in recent history.

As Pope Francis heads to Jordan, Bethlehem and Jerusalem this weekend, he’s bringing along two old friends from Argentina: Rabbi Abraham Skorka, who co-wrote a book with the Pope, and Sheikh Omar Abboud, who leads Argentina’s Muslim community.

The Vatican says it’s the first time that a pope’s official entourage has included interfaith leaders.

In a region roiled by competing religious and political visions, Francis’ chosen companions communicate an unmistakable message, church officials said.

“It’s highly symbolic, of course,” said the Rev. Thomas Rosica, a consultant to the Vatican press office.

“But it also sends a pragmatic message to Muslims, Christians and Jews that it’s possible to work together - not as a system of checks and balances but as friends.”

The visit to the Holy Land is the first for Francis as leader of the Roman Catholic Church, and just the fourth for any pontiff in the modern era.

With so much at stake - the stalled negotiations between Israelis and Palestinians, the plight of Christian refugees - the Pope’s every word, gesture and photo-op will be microscopically examined.

Already, some conservative Israelis are advocating against the Pope’s visit, scrawling anti-Christian graffiti on Catholic buildings in Jerusalem and planning  protests outside papal events in Jerusalem.

While the protesters form a fringe minority, they underscore the tensions that simmer around the Pope’s short but substantial trip.

With those challenges in mind, here are five key things to pay particular attention to.

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