A man wearing a shirt and head scarf with a Stars and Stripes motif flashes a thumbs up at a weekly rumba dance gathering in Havana, Cuba (AP Photo/Desmond Boylan)

It's a historic milestone for U.S.-Cuban relations as President Barack Obama leaves today for the first presidential visit to the island nation in nearly 90 years.

Joined by his family, Obama will stroll the streets of Old Havana and meet with Raul Castro in his presidential offices. He will sit in the stands with baseball-crazed Cubans for a historic game between their beloved national team and Major League Baseball's Tampa Bay Rays.

Obama also will meet with political dissidents. Some Cuban-Americans see Obama's outreach as a disgraceful embrace of a government whose practices and values betray much of what America stands for.

His statements alongside Castro and dissidents will be closely watched for signs of how aggressively he is pushing for reform.

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