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The ships' arrival coincided with a Latin American tour by Russian President Dmitry Medvedev, who raised his country's profile in the region in several meetings with heads of state. He also met with former Cuban leader Fidel Castro.
"Russia is looking in the region for those who are ready to think and act independently in the world. And indirectly it is also a sign to the US that we have access and good debates in your back yard," said Ivan Safranchuk of the Centre for Defence Information.
The visit to Cuba is now just one of many highlights of this naval mission. The Russian ships in Latin America have already held joint exercises with the navy of Venezuela, whose President Hugo Chavez is a fierce critic of the US.
The Admiral Chabanenko became the first Russian warship to sail through the Panama Canal since World War II.
"This visit and the entire voyage could be seen as a sign of the increasing operability of Russian war ships on one hand, and on the other it's Russia claiming its interests in Latin America and demonstrating the flag to its friends in the region," said military expert Andrey Frolov.
It is expected the fleet's commanding officers will meet with the head of the Cuban Navy and Havana's mayor, and that local residents will be allowed to visit Russian ships.
The task force, which includes the support vessels Ivan Bubnov and SB-406, left Nicaragua on Monday along with a delivery $US 200 thousand worth of medicine, computers and other humanitarian aid.
The nuclear-powered cruiser Peter the Great, the submarine-hunting destroyer Admiral Chabanenko and support ships arrived in Venezuela in November for naval exercise dubbed `Venrus 2008' in the Caribbean.
The operation was widely seen as Moscow's response to Washington's decision to deliver aid to Georgia aboard warships following the country's conflict with Russia in August this year.
Soviet ships and planes regularly visited Cuba during the Cold War, but Russian troops have been absent in the region since the Soviet Union dissolved in 1991.
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