Starwood signed a deal on Saturday to renovate and run three Cuban hotels, returning U.S. chains to the island more than 50 years after American hotels were taken over by Fidel Castro’s socialist revolution.

All Cuban hotels are state-owned so the deal puts a major U.S. corporation directly in business with the Communist government under a special U.S. license that pushes Washington’s legal dismantling of the Cuban trade embargo further than ever before. In a once-unimaginable arrangement, a hotel owned by the tourism arm of the Cuban military will become a Sheraton Four Points.