Decades of punitive US sanctions on Cuba will be rolled back as early as Friday, in a move to swiftly normalise relations between the long-estranged countries.

From reversing the ban on foreign ships entering American waters to allowing travellers to return with $100 worth of cigars, the new guidelines published by the US Treasury go as far as possible to uphold Barack Obama’s pledge in December.

Though still constrained by legislation prohibiting fully liberalised tourism and free trade, several newly announced measures suggest a deliberate attempt to flood the communist economy with American technology and money in a bid to weaken its government’s grip on power and political dissent.

The steps include raising the limit on remittances from Cubans living abroad to up to $10,000, allowing internet and mobile phone companies to export equipment and relaxing almost all banking restrictions between the two countries.

Personal travel is still restricted to 12 designated categories, ranging from professional meetings through to educational activities, but removing the need to seek a licence for these suggests determined US tourists will find it much easier to make visits.

The new rules, which come into effect on Friday, follow Cuba’s recent decision to release political prisoners as part of the historic deal brokered with help from the Vatican in December.

The scope of the Treasury and Commerce regulations, however, is likely to rekindle opposition among critics in Congress who say that encouraging trade and travel will only bolster the Cuban regime’s grip on power with little political reform promised in return.

The White House argues the reverse is true.

“These changes will immediately enable the American people to provide more resources to empower the Cuban population to become less dependent upon the state-driven economy, and help facilitate our growing relationship with the Cuban people,” said Obama press secretary Josh Earnest.

“The policy of the past has not worked for over 50 years, and we believe that the best way to support our interests and our values is through openness rather than isolation.”

“Cuba has real potential for economic growth and by increasing travel, commerce, communications and private business development between the United States and Cuba, the United States can help the Cuban people determine their own future,” added Treasury secretary Jack Lew.

US officials also hinted at the imminent possibility of direct scheduled flights between American airports and Cuba once further regulatory reviews are carried out by the Federal Aviation Administration and the Department of Homeland Security.

“I think you can expect further clarification from those agencies about the next step,” one senior administration official said during a background call for reporters when asked about regularly scheduled flights.

“This does change the travel restrictions dramatically,” the official added. “Over time, as the Department of Transportation and the Department of Homeland Security are able to implement their required steps, it is possible under these changes that we could have regularly scheduled air travel and that could mean that you as a traveller could go online to buy a ticket. You would still need to certify that you fall within one of the existing categories, but this could simplify things.”

Officials warned however it would be still be against the law for US citizens to travel directly or indirectly without proving they fall within the recently expanded categories, and they would be required to keep documents showing how they fit within them for five years or face penalties.

In a notice released later on Thursday, the Department of Transportation announced that the US government would engage with the government of Cuba “to assess our aviation relations and establish a bilateral basis for further expansion of air services”.

The notice also said that “any carrier holding long-dormant US-Cuba authority would enjoy no advantage”. According to Conde Nast Traveler, this is a blow for United Airlines, which inherited Pan Am’s flying rights.

Before regular airlines can begin flying between the US and Cuba, the Cuban government must negotiate a bilateral Air Service Agreement with the US Department of Transportation.

One-off charter flights – which are currently the only options for travellers looking to get to Cuba from the US – do not require this agreement, but for regular flights to commence, the two governments will have to agree to give an airline approval to operate a specific route.

Amedeo Odoni, a professor of aeronautics at MIT who specialises in air transportation system infrastructure, told the Guardian that these agreements come in many shapes and forms, “from very restrictive to very ‘liberalized’”.

“The US, as a policy, pursues liberalized agreements,” Odoni said. “But it is possible the Cubans may wish to impose certain restrictions on which US airlines can fly to Cuba, from/to where, how often, etc.”

Additional reporting by Nicky Woolf and Alan Yuhas