WASHINGTON — On his history-making trip to Cuba, President Barack Obama plans to chop down another set of barriers that for generations kept Americans and their money out of the island they once dominated. Getting Cuba to reopen to America is proving harder.

Hungry for dollars but wary of U.S. influence, Cuban President Raul Castro's government has taken only a few cautious steps to allow U.S. commerce and tourism to return.

Even as Obama's administration prepares to let more Americans travel and businesses operate in ways unimaginable just two years ago, it's unclear how far Cuba will bend.

In a bid to show growing momentum, the Obama administration is preparing to further ease restrictions and green-light projects by U.S. companies in connection with Obama's trip to Cuba starting Sunday, according to individuals familiar with the administration's plans.

Starwood, the hotel chain whose brands include Sheraton and Westin, is expected to get formal U.S. approval in the coming days. It has applied for a license from the Treasury Department's Office of Foreign Assets Control, which would allow it to operate in Cuba despite congressional sanctions.

Yet Cuba's resistance to letting foreign companies build or own property makes it more likely Starwood would manage existing hotels, not build them.

Another hurdle: Foreign business can't hire workers directly. Employees work for a Cuban hiring agency that keeps much of their salaries. The U.S. hasn't yet managed to get Cuba to announce it will ease that policy.

For Cuba, any American footprint carries uncomfortable echoes of the decades before its 1959 revolution, when American business and organized crime worked hand in hand with U.S.-backed strongmen to dominate the island's economy and politics.

“In Congress, there's a lot of criticism from my Republican colleagues about getting this or that before going down there,” said Rep. Peter Welch, D-Vt., one of dozens of lawmakers joining Obama's trip. “But the big decision is, do you want to be engaged or not?”

A Marriott spokesman said that chain was also hoping for approval soon, and its CEO, Arne Sorenson, was traveling in Obama's delegation. Carnival Cruise Line, which already has U.S. approval, said it expects Cuban approval soon after months after waiting and plans to sail starting May 1.

The Obama administration is also poised to remove another roadblock for travelers, allowing Americans to travel independently for educational purposes rather than in organized group trips.