Peter the Great heads the fleet travelling 15,000 miles to Venezuela
Russian warships have set off for Venezuela for joint exercises unprecedented since the Cold War.
The fleet of ships, headed by the nuclear-powered Peter the Great cruiser, set off from its base at Severomorsk in the Arctic.
The ships are due to take part in joint manoeuvres with Venezuela in November.
The move is seen as a rebuff to the United States, which is facing increasingly fraught relationships with the two nations.
Russian Navy spokesman Igor Dygalo said the ships set sail at 1000 local time (0600 GMT), and would travel 15,000 nautical miles to reach their destination.
"It's the nuclear-powered guided missile cruiser Peter the Great, the anti-submarine warship Admiral Chebanenko and other accompanying ships," he told the AFP news agency.
Two Russian bombers arrived in Venezuela last week for training flights.
On board Russia's Peter the Great warship
Moscow has intensified ties with Venezuela and other Latin American countries recently as its relationship with Washington has become strained.
Caracas and Moscow have signed arms contracts, and are looking to extend bilateral co-operation on energy.
Russian Deputy Prime Minister Igor Sechin, in Caracas last week, said five Russian oil firms were looking to begin operations in Venezuela.
Venezuelan President Hugo Chavez, who will visit Moscow this week, said on Sunday that Latin America needed a strong friendship with Russia to help reduce Washington's influence in the region.
A staunch critic of the US, he backed Russian intervention in Georgia last month and has accused Washington of being scared of Moscow's "new world potential".
Mr Sechin also warned the US not to view Latin America as its own backyard. "It would be wrong to talk about one nation having exclusive rights to this zone," he told the Associated Press.
During the Cold War, Latin America became an ideological battleground between the US and the then USSR.