Cuba Trip Marks New Diplomatic Territory for N.Y. Gov. Andrew Cuomo

Cuomo plans a two-day trade mission to Cuba, but gay-rights advocates press him to use his influence.

When New York Gov. Andrew Cuomo lands in Cuba on Monday morning, he will become the first sitting governor to enter the communist nation since the U.S. announced it would restore diplomatic relations with the country—and he will find himself in far more delicate diplomatic territory than he has ever encountered.

Mr. Cuomo, a Democrat, is set to lead a two-day trip to the country, ostensibly to encourage trade between New York state and Cuba. He will bring a delegation of 20 business executives, representing five sectors: travel, financial services, health care, agriculture and education, according to a senior administration official.

His travel has taken him to the center of foreign-policy debates several times in the past year, particularly during an Israel trip last summer when he met with Prime Minister Benjamin Netanyahu during a low point in U.S.-Israel relations. In September, Mr. Cuomo visited Afghanistan as part of a U.S. military-sponsored excursion.

But Cuba represents the freshest and most fluid foreign-relations circumstance Mr. Cuomo has broached. He decided on it in the days following President Barack Obama’s announcement of eased travel restrictions to the country, and it comes at a sensitive political moment for the two nations.

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