At least 30 students from Pierson High School in Sag Harbor, along with Spanish teachers and an art teacher, will be taking a trip to Cuba in February.
Tensions between the United States and Cuba have lessened in recent months since President Barack Obama eased travel and trade restrictions to the country.
Teachers say they hope this trip will give students a new perspective on Cuba's history and culture.
"I'm very curious to see what they take away from this whole experience," said teacher Peter Solow.
Over the past 15 years, Pierson students have traveled to Italy, France, Hawaii and Spain.