PITTSBURGH (KDKA) — Cuba, with relaxed relations with the U.S., has become an exciting destination for Americans, now including Pittsburgh School Superintendent Anthony Hamlet and four of his top administrators.

KDKA Investigates has learned that over spring break, the group of Pittsburgh educators flew to Miami at district expense and from there were flown down to Havana and parts beyond. The two-day tour of the island is described as an “expedition,” an out-of-country trip without the required approval of the school board.

“I can’t believe that they actually went on a trip, left the country and thought that that was going to be OK. It’s hard to believe that they would do that,” City Controller Michael Lamb said.

After arriving in Florida, the group became the guests of the Flying Classroom, an educational organization headed by pilot Barrington Irving, who flew them to Cuba.

Video from his website shows Irving hosting a group of educators from Virginia on a similar Cuban trip and sources say, like the group from Virginia, Hamlet and the others enjoyed beach visits, snorkeling and cave-diving there.

In October, Irving gave superintendent Hamlet a helicopter ride around the school district, kicking off a $73,000 contract to provide science curriculum to Langley and Brashear high schools, and sources say Flying Classroom is looking to expand its role here next year.

Thursday, through the district spokesperson, Hamlet declined to be interviewed on camera about the spring-break trip and would not respond to specific questions. He issued a statement, which fails to mention the side trip to Cuba.

The statement says, “As part of our partnership, Flying Classroom holds Leadership Expeditions to ensure the executive team fully understands the learning happening in the classroom. One of these Leadership Expeditions for PPS was scheduled during Spring Break in Miami.”

Lamb says by appearances, this trip to Florida and Cuba is a promotional junket that violates the district policy of not accepting gifts or anything of value “from any party doing business with the district or interested in doing business with the district.”

“If a vendor is paying the way, there’s an obvious kind of quid pro quo question there. Why is he doing that? Why is he fronting all that money? He’s clearly trying to get a contract, another contract, with the school district, and it just raises a lot of problems,” Lamb said.

In forms obtained by KDKA, school board president Lynda Wrenn signed off on Hamlet’s trip and Hamlet in turn authorized the travel for administrators Minika Jenkins, Jamie Griffin, Kendra Wester and Vince Scotto. The district paid a total of $3,595 for their airfare.

But according to another board policy, any out-of-the-country trip must be approved by the full board of education at a regular meeting. This did not happened. The board also requires a full written report on trips to be submitted within 15 days, and yet, no report has been filed.

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Last year, KDKA Investigates questioned Hamlet about more than $300,000 spent on district travel. Of that $300,000, $16,000 was spent by Hamlet himself.

“When we say travel, we’re talking about professional development, conferences and workshops that we go to. This is not something that we’re going to and sitting on the beach and having a good time. This is work,” Hamlet said at the time.

Wrenn told KDKA’s Andy Sheehan she signed off on the trip but was not aware that the group would be leaving the country, which would have required the approval of the full board. Wrenn says she will conduct her own investigation.