Fifty years ago this month, the United States began the embargo on Cuba which continues to this day. But the country against which it was aimed is rapidly becoming a very different one to the alleged communist menace just 90 miles off the coast of Florida. Under Fidel Castro's brother, Raul, it is in the throes of a second Cuban revolution.

For a sign of the change which is turning life on their island on its head, the people of Havana have only to peer into the night at the northern horizon. This month, Repsol, the Spanish energy company started drilling the first oil well from a massive and brightly lit rig, the lumbering Scarabeo 9, built in China for ENI of Italy. This morning it will still be grinding away seeking the billions of barrels of oil and the trillions of cubic feet of gas that the US government, among others, says lie under Cuba's offshore waters.

The Spanish oilmen working on the structure, which has been towed halfway around the world amid US efforts to delay its progress, will be followed aboard by a succession of Norwegians, Russians, Indians and Malaysians.

Optimistic geologists reckon that within a few years the island – long cursed by a lack of oil supplies, half of which it has had to import – will actually be exporting the stuff. And it will be able to do so without the aid of President Hugo Chavez of Venezuela who has kept the island's motors, power and air-conditioning going with his subsidised crude.

Also, at the fine harbour in Mariel, a few miles to the west of the Cuban capital, is another pointer to the future, the big island-changing harbour that Odebrecht, the Brazilian construction giant, is building with a large wodge of money provided by the booming South American nation.

The end of the first national conference of the Cuban Communist Party set the seal last month on changes that President Raul Castro had been building up to. Since he took over from his ailing elder brother, Fidel, in 2006, the new president, himself an octogenarian, has pushed ahead with measures which are turning the traditional Cuban lifestyle upside down by decreeing that the party will henceforward cease micro-managing daily life and confine itself to strategic matters.

Landscapers are working hard on matters of equally urgent national strategy. Fifteen more golf courses and new marinas are being laid out in Cuba and they can't be finished quickly enough: golfers from abroad will even be able to lease chalets and timeshares. The island's hotels are packed. European visitors are pouring in. After decades of US-imposed isolation from high-speed internet, Cubans and their visitors are finally beginning to receive it via a new cable laid from Venezuela.

Yet Raul's strategies are not confined to big infrastructure projects; they reach down deeper into an effort to keep Cuban society together. Senior Cuban figures make no secret of the fact that even more important work has to be done to improve Cubans' ideological outlook and the economic conditions.

"Whole generations have long since grown up with no personal knowledge of the heroic days before and after what we call 'the Triumph of the Revolution'," says one. New Year's Day 1959 was when General Fulgencio Batista, a dictator armed and honoured by the West, fled with suitcases of banknotes and valuables as Castro's forces got their hands on Havana. Few remember the abortive 1961 Bay of Pigs operation, the tragi-comic fiasco of Presidents Dwight Eisenhower and John Kennedy to conquer the country.

The US embargo, introduced on 7 February 1962, is a constant talking point for island authorities, who blame it for shortages of everything from medical equipment to the concrete needed to complete an eight-lane highway running the length of the island. Cuba frequently fulminates against the "blockade" at the United Nations and demands the US end its "genocidal" policy. Every autumn, like clockwork, the vast majority of nations agree, and overwhelmingly back a resolution condemning the embargo. Last November, 186 countries supported the measure, with only Israel joining the US.

Wayne Smith was a young US diplomat in Havana in 1961 when relations were severed. He returned as the chief American diplomat after they were partially re-established under President Jimmy Carter. "We talk to the Russians, we talk to the Chinese, we have normal relations even with Vietnam. We trade with all of them," Smith said. "So why not with Cuba?"

The United States actually does have significant trade with Cuba under a clause allowing the sale of food products and some pharmaceuticals. According to the most recent information available from Cuba's National Statistics Office, the US was the island's seventh-largest trading partner in 2010, selling $410m (£260m) in mostly food products. However, that was down from nearly $1bn in 2008, as the island increasingly turned to other countries that don't force it to pay cash up front.

As Raul gave his closing speech at the party's first national congress, it was announced that new laws would allow people to sell their crumbling houses and wheezing cars. With the lonely support of only one ally, Israel, Washington has insisted on continuing six decades of crippling boycott on trade with Cuba despite overwhelming condemnation of it in the UN for the past 19 years.

But no longer will Cubans be obliged to leave their homes or their vehicles to their children, or do dodgy swaps with strangers. More than one million of the 4.3 million state employees will be encouraged to form co-operatives or start private businesses in a mass of trades and professions up to now reserved to the state.

"China is an example. No other country has lifted so many people out of poverty. This is something of which the Chinese people and government should be proud, and which the rest of the world admires," official daily Granma said in October 2009, echoing Fidel's words. Like China, or more likely Vietnam, the island will remain a one-party state.

"To renounce the principle of only one party would simply mean legalising the party or parties of imperialism on Cuban soil and sacrifice the strategic weapon of one party," Raul declared last Sunday. The president added that he would be merciless in punishing corruption, especially if the culprits were party members.

Next month the Pope, Benedict XVI, arrives on the island at the end of an unprecedented religious act. In 2010 Raul allowed the public veneration of a statue of the Virgin of Charity, the island's patroness, which was driven for 425 days from one end of Cuba to the other on top of a van.

Oil, mass tourism, private enterprise, broadband internet, organised religion – the brakes are coming off a society which today looks less towards Marx and Lenin and more toward its native-born 19th century hero, José Martí, who died in the battle for Cuban independence from Spain in 1895. God alone knows what's coming next.