Will the United States and Cuba ever find a way to patch up their differences and start to get along?

To judge by a recent flurry of activity on both sides of the Straits of Florida, you might easily be forgiven for thinking they might.

Of course, you might just as easily be wrong.

“I’m hopeful, but I’m skeptical, of much change in U.S.-Cuban relations,” says Jorge Dominguez, a professor of Latin American studies at Harvard University. “The record is so depressing. Who knows what’s going to happen?”

But consider the following:

After decades of intransigence, a reformist leader finally holds power in Cuba, never mind that his surname still happens to be Castro. At least, this Castro doesn’t wear a beard.

At the same time, an emboldened, second-term president occupies the White House in Washington, with a new, liberal-minded secretary of state at his side and likely a hankering to carve out a historical legacy for himself.

Meanwhile, in Florida, some 1.8 million Cuban Americans seem largely in favour of improving ties between their adopted country and their ancestral island home.

Still, old habits die hard, and it remains far from clear whether bitter tensions between the two sides will ease any time soon, despite a program of economic reforms being enacted by Cuban president Raul Castro, who formally took over from his ailing brother Fidel in 2008.

“Any one of these changes tends to be tiny,” says Dominguez, referring to the spate of Cuban reforms. “I mean really tiny. But if you look at the pattern, the pattern is really pretty impressive. The steps are all in the right direction.”

Cubans may now own, buy or sell large commodities, including houses and automobiles. They may launch various kinds of small businesses — barbershops, beauty salons, some forms of merchandising, as well as taxi services — and operate them with a mind to turning a profit. The government has also repealed a detested law that severely restricted the ability of Cubans to travel abroad.

This past Sunday, while announcing his intention to retire from office in five years, Raul even offered an unprecedented glimpse of what Cuba might look like without a man named Castro at the helm.

With Fidel himself gazing on, Raul introduced his own heir apparent — a 52-year-old former electrical engineer named Miguel Diaz-Canel Bermudez, a man who was not even born much less wielding a rifle when the Castro brothers and Ernesto “Che” Guevara seized power in 1959.

A long-time Communist Party insider, Diaz-Canel now becomes first vice-president, Cuba’s most powerful figure after Raul — the clearest signal yet of a generational shift in the island’s leadership.

Depending on how you look at it, this changing of the revolutionary guard is either an example of enlightened political vision or a simple case of biological realism.

After all, the “younger” Castro is already 81 years old and would be 86 at the time of his anticipated retirement, assuming he lives that long.

“Let’s be honest,” says Ariel Armony, head of the Latin American studies program at the University of Miami. “In five years, you won’t have many historicos left. It’s absolutely obvious you are going to have generational change.”

The term historicos refers to the once-youthful fighters who waged the Cuban revolution at Fidel Castro’s side. Like Fidel himself, they are old men now, stooped and grey — and dying. They may not want to surrender power, but they have to.

Similarly, the economic reforms being enacted under Raul seem driven more by sheer necessity than anything else.

“The reforms are important,” says Carmelo Mesa-Lago, author of a recently published book on the Cuban economy under Raul. “But, despite this, they are not fast enough or deep enough to accommodate all the problems in the Cuban economy.”

Political changes have been even slower to emerge, although a space for peaceful dissent does seem to be opening, a shift that is most apparent in the government’s willingness to tolerate the online activities of bloggers such as Yoani Sanchez, most prominent of a new breed of independent political activists in Cuba.

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Now travelling outside Cuba, Sanchez will be returning to the island before long, presenting something of a test case for the government. Will they let her back in?

John Kerry, the newly minted U.S. secretary of state, will undoubtedly be watching to find out.

Formerly chairman of the U.S. Senate Committee on Foreign Relations, Kerry openly favours improved ties with Havana and opposes U.S. efforts to destabilize the Cuban government.

An increase in diplomatic activity across the Straits of Florida is already underway.

Late last month, a seven-member U.S. congressional delegation led by Vermont Democrat Patrick Leahy traveled to the island and held wide-ranging talks with Castro and other top officials.

They were unable to resolve the case of American Alan Gross, whose imprisonment in Cuba remains a festering source of discord between the two governments.

Gross was jailed for 15 years in 2009, after the Cubans convicted him of bringing satellite communications gear into the country, part of an effort to provide the island’s miniscule Jewish community with secure access to the Internet.

Washington refuses to negotiate other bilateral disputes until Gross is freed and won’t consider Cuban suggestions of a prisoner swap — the American’s freedom in exchange for the release of several men known collectively as the Cuban Five, who were convicted of espionage in Florida in 2001 and sentenced to long prison terms.

In many ways, the dispute over Gross is just the latest in a series of entanglements that have long frustrated efforts to improve relations between the two sides. This pattern of failure dates back to the early 1960s, when Washington imposed an embargo on trade with the island, a measure that has caused little but trouble since.

“The Cubans box themselves in,” says Harvard’s Dominguez, “and the U.S. administration boxes itself in.”

Still, many observers remain hopeful of better times ahead.

“By the end of four years, we may not have lifted the embargo, but I would expect normal relations,” says Wayne Smith, formerly the top U.S. diplomat in Havana. “Let’s hope I’m right.”