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

— -- President Obama will depart Wednesday evening for a three-and-a-half-day trip to Jamaica and Panama for a series of meetings at which the U.S. relationship with Cuba is expected to take center stage.

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?

All eyes will be on whether an historic meeting occurs between President Obama and Cuban President Raul Castro on the sidelines of the Summit of the Americas in Panama on Friday and Saturday. The White House has hinted an encounter between the two leaders will likely occur, though a formal meeting has not been scheduled. "I'm sure that President Obama will be interacting with President Castro at the summit events and as the leaders gather on the margins of those events," Ben Rhodes, deputy national security adviser, said on a conference call Tuesday. If Obama and Castro do have any substantive talks in Panama, this would be the first meeting between a U.S. president and Cuban president in nearly 60 years -- the latest development in President Obama's efforts to normalize relations between the two countries. Over the past year and a half, Obama and Castro have engaged in limited -- but history-making -- interactions. In December, the two leaders conducted a 45-minute phone conversation ahead of an announcement that the U.S. and Cuba would try to restore diplomatic ties. Obama and Castro also shook hands at a memorial service for Nelson Mandela in 2013. But many are hoping a more substantive conversation could occur on the sidelines of the summit.

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

It could happen at any moment. The State Department started its review of whether Cuba should remain on the state sponsors of terrorism list in December and is nearing the conclusion of its assessment. Once President Obama receives the official State Department review, he will make his recommendation, which could occur during his trip to Jamaica and Panama. Removing Cuba from the state sponsors of terrorism list would be the latest major step in efforts to normalize relations between the U.S. and Cuba. Currently, Cuba, Iran, Sudan and Syria all are on the list. Cuba was added in 1982 based upon accusations it provided weapons and training to rebels in Latin America.

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?

While President Obama has earned some good will from Latin American countries in recent years, there are some who aren't too happy with the president's actions. Case in point: Venezuela. Last month, President Obama imposed sanctions on seven Venezuelans over alleged human rights abuses and corruption in the country. The decision angered Venezuelan President Nicolas Maduro and some of his allies in the region. Maduro is also scheduled to attend the Summit of the Americas, and while there is no meeting between the two leaders on the schedule, expect Maduro to express his displeasure towards the United States at some point over the weekend. The White House tried to downplay some of the tension ahead of the trip. "We certainly would expect the Venezuelan government to express its opposition to certain U.S. policies," Rhodes said. "What we'll be making clear here is that we stand up for a set of universal values everywhere. And with respect to Venezuela, frankly, we believe that a process of dialogue within the country and within the region is the best way to address the issues that have raised so many challenges within Venezuela and the region in recent years."

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?