UPDATE: President Trump is on his way to Miami, where he's expected to announce a shift on his administration's Cuba policy. New rules will target the Cuban military but largely leave the tourism industry alone – at least, airlines and cruise ships.

But The Washington Post's Drew Harwell and Jonathan O'Connell report that Trump's policy moves could, in the long run, benefit his personal businesses:

... as a businessman whose properties include golf resorts and luxury hotels from Florida to Scotland to Dubai, Trump in the past has signaled his interest in the potential financial opportunities in Cuba.
He told CNN last year that he would like to open a hotel in Cuba “at the right time, when we’re allowed to do it.”
As part of an ethics pledge, Trump’s company has vowed to pursue no new foreign deals during his presidency, making a potential foray into Cuba off limits for now. Yet, according to one industry expert, a presidential directive restricting efforts there by Starwood or other hotel chains would, in effect, neutralize a chief rival’s ability to gain an early advantage.

In that context, we're re-posting a story from November 2016, just after Fidel Castro died. Below is my original post about a trip I took to Cuba as a high school student in 2004:

The first moment we really understood we were in a communist country was when we saw the men with Soviet-era machine guns and stars on their epaulets.

Not that we weren't supposed to be there. Our group of 18 students and two teachers had an educational visa to visit Havana and a few other cities in Cuba over the course of 10 days in the spring of 2004. We'd go on to taste rum, puff cigars, dance to jazz with locals and drink at Hemingway's bar. We'd also see the stark contrast between the tourist-filled avenues of downtown Havana, with its American-dollar mini-economy, and the poor rural farmers and villagers who live outside of Havana.

But first we had to get through Cuban customs and immigration.

It's a weird experience as an American. I remember the immigration officer asking me whether I wanted my American passport stamped with a Cuban entry marker — yes, it was an option. As I had a special visa from the U.S. government, I was good to go, but other Americans apparently made a habit in those days of flying in from Mexico, or somewhere in South or Central America, and slipping immigration officers a few bucks to get through without a passport stamp.

That was our introduction to the realities of the uneasy standoff between Cuba and the United States. The plane, which had flown from Miami, carried our group of students, Cuban exiles living in the States who were permitted to visit family members briefly and a group of clowns — Patch Adams, the physician and activist, was taking a group of clowns from his Gesundheit Institute to visit children in Cuban hospitals.

As we walked outside the small, hot airport terminal, we were met by the faces of hundreds of Cubans searching for the faces of their loved ones who'd come with us on the flight from Miami. Or perhaps a few hoped they could somehow make it to one of the planes themselves. We soon met our guides — one American, a woman from San Francisco, and Victor, our Cuban government minder.

Meeting Victor and hearing his story turned out to be the most powerful experience on the trip. His job was to keep us to the areas the government wanted us to see, I'm sure. But that doesn't mean his loyalty was entirely to the government that paid his salary. In fact, his story turned out to be a whole lot more complicated.

At the time, I wrote in a letter to family and friends:

We soon learn from our Cuban guide, Victor, that things like capitalism and civil rights are distant or even irrelevant for the Cuban people. Even though he is allowed regular contact with foreign tourists, Victor is allowed in the lobby of the hotel we stay in only to meet us in the morning. He isn't allowed in the restaurants. He cannot shop in the hard-currency stores we patronize. We take for granted that in the U.S. there is no rationing, but as we learn from Victor, Cubans are allowed only a certain amount of food per month. And while Victor lives this life of oppression and exclusion, he waits for the day when he will be able to join his wife and son, from whom he has been separated for years, in Miami. So close to getting a visa to study in the United States several years ago, Victor does not know when or how or even if he will ever see his family again.

I wasn't really able to stay in touch with Victor after our trip. But things were looking up for people like him, with families split between the U.S. and Cuba, under the Obama administration. Fidel Castro's death could pave the way for even more open relations between the two countries. But it's hard to say, under the incoming Republican administration, whether that will be the case.

I came back from Havana with a new perspective, and a glimpse of one of the few remaining communist countries in the world. But I also had something Victor may never have: A ticket back the United States. As our plane taxied away from the terminal, he was left behind — with the wonderful food, the amazing music, the culture that spills out of every doorway onto the Havana streets. And left behind without his family, without the right to protest or demonstrate for the things he believes in, but with the hope that someday, things just might get better.