President Barack Obama will use his historic trip to Cuba to chip away at key remaining U.S. obstacles to travel and commerce with the communist island, working to push his diplomatic relaunch past the point of no return before he leaves office.

The three-day trip to Havana beginning next weekend marks the first time a sitting president will set foot in Cuba in nearly nine decades. It also is one of Obama's final opportunities to lock in the sharp reversal in policy toward Cuba that his administration launched. In a bid to show growing momentum, the Obama administration is preparing to further ease restrictions and greenlight projects by U.S. companies in connection with the trip, according to a half-dozen individuals familiar with the administration's plans.

Starwood, the hotel chain whose brands include Sheraton and Westin, is expected to receive a license from the Treasury Department in the coming days to operate hotels in Cuba, following extensive conversations with both Cuban and U.S. officials. If successful, Starwood would become the first and only U.S. hotel company with operations in Cuba.

The Connecticut-based chain, which is being purchased by Marriott, is exploring numerous possibilities for Cuba that include managing the famed Hotel Saratoga in central Havana, said the individuals, who weren't authorized to discuss the plans publicly and requested anonymity. Starwood is one of a number of major U.S. hotel chains actively working on plans to expand to Cuba.

Starwood declined to offer specifics but confirmed it has applied for a license from Treasury's Office of Foreign Assets Control, which would allow it to do business in Cuba despite congressional sanctions. A Marriott spokesman said that chain was also hoping to "get a green light soon" from the U.S. to operate Marriott-branded hotels in Cuba, adding that CEO Arne Sorenson planned to travel there for Obama's trip.

The White House declined to comment on any potential announcements related to Cuba policy or Obama's trip.

The Obama administration is also poised to remove yet another roadblock for those who wish to visit Cuba by allowing Americans to travel independently, rather than in organized, group trips. Already, Obama has eased travel restrictions by allowing Americans traveling for one of 12 approved purposes to go without obtaining a specific license, but the forthcoming regulatory tweaks will remove the requirement that Americans go through structured trips with set itineraries, the individuals said.

Getting to Cuba remains tricky; chartered flights are currently the only option. Last month the U.S. and Cuba signed a deal restoring commercial flights for the first time in five decades, triggering a flood of applications from U.S. airlines. Though the coveted slots to fly to and from Havana are contested among multiple airlines, there was less competition for flights to other airports like Varadero and Holguin. The public comment period ends March 21 -- while Obama is in Havana -- but it could be a few more months before the Transportation Department formally awards new routes.

At the heart of Obama's strategy of expanding travel and commerce in Cuba is a belief that economic ties can eventually improve life for Cubans, said Ben Rhodes, Obama's deputy national security adviser and a key architect of his Cuba policy. He said the more Cubans interact with Americans, enjoy business opportunities and have access to information about the outside world, the more pressure there will be on Cuba's government to loosen its grip on society and improve human rights.

"I don't think we're there yet," Rhodes said in an interview. "But if we can use the remaining time to create opportunities for U.S. businesses to operate in Cuba, with direct flights and more Americans traveling, and to demonstrate this is improving the lives of ordinary Cubans, all those factors will make this irreversible."

Aside from travel tweaks, Obama is expected to come with a series of announcements from U.S. companies that plan to launch operations in Cuba, particularly related to Internet and telecommunications, people familiar with the planning said.

Yet while Obama can punch wide holes in the U.S. embargo, he can't lift it unless Congress repeals the sanctions. The White House also said it wasn't considering changing the "wet foot, dry foot" policy allowing those who reach U.S. soil to stay here.

Ahead of the trip, Obama has faced criticism from opponents of the policy for rewarding Cuba with a visit before its government has taken substantial steps to improve human rights.

"There has not been a single democratic opening; not a single change on the island in human rights," Florida Sen. Marco Rubio, a Cuban-American presidential candidate, said in Thursday's GOP debate. "In fact, things are worse."

The White House has stressed that Obama plans to meet while in Havana with Cuban dissidents that the White House -- not the Castro government -- will pick.