Russian navy ships arrived in the Cuban port of Havana on Wednesday ahead of planned military exercises in the Caribbean.
The four-ship group included a frigate, a nuclear-powered submarine, and two support vessels – a fuel ship and a rescue tug.
The mission comes less than two weeks after President Joe Biden authorised Kyiv to use US-provided weapons to strike inside Russia.
The Russian defence ministry says the group of four vessels conducted missile drills in the Atlantic Ocean en route to Cuba.
These included the use of high-precision missiles on targets using a computer-based maritime simulation.
Washington says it will closely monitor the ships which are expected to remain in Havana until 17 June.
Cuba said last week that the visit was standard practice by naval vessels from countries friendly to Havana.
Russia's foreign minister, Sergey Lavrov, meanwhile hosted his Cuban counterpart for talks in Moscow on Wednesday, thanking Havana for its position calling for a diplomatic solution in Ukraine.