President Obama’s Trip to Jamaica and Panama: 5 Things to Watch

The president could meet with Cuban President Raul Castro in Panama.

The president will first travel to Kingston, Jamaica, where he will meet with Caribbean leaders to discuss everything from security efforts in the region to energy, as well as speak to students in Jamaica. It will mark the first presidential trip to Jamaica since 1982.

He then will fly to Panama City for events with CEOs, Central American leaders and others before attending the Seventh Summit of the Americas, which, for the first time, will be attended by all 35 countries in the Western Hemisphere -- including Cuba.

Here are five things to watch on President Obama's trip to Jamaica and Panama.

1. Will Obama and Castro Meet?

2. Cuba Could Be Removed From the State Sponsors of Terrorism List

3. Changing Expectations

Expect this Summit of the Americas to be much different than the last one. At the VI Summit of the Americas held three years ago, President Obama left the meeting arguing against inviting Cuba. This year, Cuba will be in attendance for the first time following the restoration of diplomatic ties between the two countries. The embargo with Cuba was one of several issues of contention between the U.S and Latin American countries at a previous summit held in Columbia. Anti-drug/counternarcotic and monetary policy also left Obama on the defensive. This time, President Obama has not only moved forward with Cuba. Add in the $1 billion request for foreign aid to assist Central American countries with security and economic investments, and you can expect Obama to be received with open arms. "This is our third summit, and we've been building a more positive environment in the Americas for several years now," Rhodes said. "What we're building is a very significant series of initiatives within the hemisphere, and the president is very focused on ensuring that we are ambitious and having a concrete agenda here."

4. But How Will Venezuela React?

5. President Obama, the Tourist

As with every presidential trip, there is always the opportunity for the president to play tourist. Will Jamaica roll out the red carpet to welcome the president in full Jamaican flair in Kingston? Could the president swing by the Panama Canal, which is currently undergoing an expansion that would double its capacity? Will he pick up any gifts in Jamaica and Panama for first lady Michelle Obama and their daughters, Malia and Sasha?