Cuba, the only one-party communist state in the Americas, began opening up its economy in 2008, but has not grown as much as hoped and could desperately use more Chinese investment.
Xi for his part has made a point during his tour of reaching out to countries often shunned by US and European investors, including Venezuela and Argentina as well as Cuba.
"This visit will realise the aims of boosting friendship, deepening mutual trust, expanding cooperation and driving development, opening a new phase in the mutually beneficial, friendly cooperation between China and Cuba," said Xi after touching down last night in Havana.
"Cuba is already fully promoting the updating of its economic model, which means new and important development opportunities for Chinese-Cuban ties," he said.
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China is already the Caribbean island's second-largest trading partner after Venezuela and its primary source of credit, filling the gap left by the US economic embargo on Cuba and its long-time exclusion from institutions such as the World Bank.
Coinciding with Xi's trip, about 50 Chinese entrepreneurs travelled to Havana to explore business opportunities, attracted by foreign investment incentives and the future Mariel free trade zone outside the capital.
Xi is due to meet with President Raul Castro, 83, at the Palace of the Revolution, for the signing of a range of bilateral deals.
The second day of his visit will take him to Santiago de Cuba, the country's second-largest city, hit hard by Hurricane Sandy in October 2012.
The storm killed 11 people, destroyed 17,000 homes and damaged thousands more. Xi is expected to announce Chinese cooperation in the city, perhaps in rebuilding housing.
The Chinese president may also pay a visit to retired revolutionary leader Fidel Castro, 87, who led Cuba for five decades until failing health prompted him to hand power to his brother eight years ago.