The arrival extends a tour that included stops in Venezuela and Panama and shows Moscow's desire to flex some muscle in America's backyard. It comes even as President Raul Castro reaches out to the U.S., offering to negotiate directly with President-elect Barack Obama and proposing an unprecedented swap of political prisoners.
"That is Cuba's diplomatic specialty, playing both sides, or all sides, on every issue," said Daniel Erikson, director of Caribbean programs at the Inter-American Dialogue, a Washington think tank.
Russian sailors in white and tan dress uniforms stood at attention on the deck of the Admiral Chabanenko destroyer, which chugged into Havana Bay amid a cloud of gray smoke. The ships will be moored here until Tuesday, and the crew planned a tour of Havana that includes a trip to a Cuban naval school.
"Cubans knew it was coming in and they were out there," said CBS News producer Portia Siegelbaum. "It caused great excitement here in the capital. The entire waterfront drive was lined with hundreds of people, and all the cars were driving along at the same speed as the destroyer as it sailed into the Bay of Havana."
A Cuban cannon fired a 21-blast salute that rattled the windows of nearby buildings, and a naval band waiting on a cruise ship dock played the Russian and Cuban national anthems. A hulking barge that frequently ferries U.S. food to the island happened to be waiting in the area but had to move to make room for the Russian warships. It was unclear whether it had any American cargo aboard.
Washington's nearly 50-year-old trade embargo prohibits American tourists from visiting Cuba, but the U.S. has allowed cash-only sales of its agricultural products to the island since 2000 and has long since become the country's largest source of food.
Erikson, author of a new book called "The Cuba Wars: Fidel Castro, the United States, and the Next Revolution," said he was not surprised to see Russian ships come to Cuba at the same time the communist government is promoting a thawing in its relations with Washington.
"Cuba has always been a country that wants to have its cake and eat it too," he said. "They want to keep the United States as the No. 1 enemy and at the same time benefit from U.S. travel and trade."
The Soviet Union provided billions of dollars in trade and annual subsidies to Cuba before its 1991 collapse. Relations soured after that, but the Cold War allies have become close again, with Russian President Dmitry Medvedev visiting Havana in November.
Friday marked the first time Russian military ships have visited Cuba since the end of the Soviet era. About 100 Cubans - as well as tourists from Russia and other foreign destinations - watched the arrival from a nearby sidewalk. The crowd grew so large that police blocked off the right lane of a crowded boulevard adjacent the bay.
"This shows relations with Russia never deteriorated," said Eric Hernandez, a naval administrative employee who left his office across the street for a closer view. "Russia is a brother nation to Cuba, and Cuba has brother nations all over the world, despite what the United States wants."
But another onlooker, retired airport employee Jorge Fernandez, said he hoped the Russian visit wouldn't send Washington the wrong signal.
"The new president of the United States wants peace and tranquility with Cuba," he said. "This is positive for Cuba and Russia. But they might not agree in the United States."
The Russian ships arrived as Castro was set to return from his first state visit to Brazil, where he said Thursday he would consider releasing some jailed political dissidents as a gesture to opening talks with the Obama administration. Castro's trip also included a stop in Venezuela, where he met with U.S. critic Hugo Chavez.
Erikson noted that "the U.S. is important for Cuba, but it's not the only international relationship they're trying to manage."
"To some degree, the Cuban government says 'There's no way of knowing what the U.S. will do ultimately so we better have relationships with Russia, Brazil and China in our back pocket,"' he said. "It's hard to imagine Cuba saying 'We don't want Russian warships to come,' because they don't know what the U.S. will do."
The Russian ships' trip to Cuba has largely failed to register in Washington, but State Department spokeswoman Heidi Bronke rejected Castro's offer of a prisoner swap, saying the more than 200 jailed dissidents should be released immediately without conditions. Castro said the U.S. would need to release the so-called "Cuban Five," who were convicted in 2001 on U.S. espionage charges.
Cuban human rights activists also have panned the notion of a prisoner exchange, saying the jailed activists, independent journalists and political dissidents should not be used as bargaining chips.
In a statement Friday, the country's best-known political opposition leader, Oswlado Paya, called on Castro to free political prisoners without asking for anything in return, saying doing so "would be an act of justice for the people of Cuba, and is a moral and political obligation for the government."