Facing severe economic distress, with shortages of such critical commodities as gasoline and some foods, Cuba is relying on a ready source of revenue: tourism, and specifically urban tourism, of a higher caliber than the low-budget, all-inclusive beach resort holidays that have long attracted bargain-hunting Europeans and Canadians.

The recent splendid renovation and adaptive- reuse projects in Havana have included the resurrection of long-shuttered historic hotels and the refurbishment of grand and gaudy gangster hotels from the 1950s. The Manzana de Gómez, an early 20th-century commercial block on the Parque Central, with a Parisian-style arcade, was gutted and reborn as a five-star Kempinski hotel. The Havana skyline bristles with construction cranes at the sites of new ground-up hotel projects as well, but the quality of the architecture is mixed at best.

Two projects on prominent sites have stirred particular controversy. On the elegant Paseo del Prado, the new Iberostar Grand Packard was built within, beside, and over the shell of the historic 1920s Hotel Packard. When plans for the hotel by Rafael Moneo were unveiled, Havana's architectural community rejoiced that the city might get a world-class modern design. But after the original development team departed, the Moneo design was shelved for one decidedly less graceful. Still, with five floors of concrete and glass hovering over the historic stone facade, the building is an appropriately bold juxtaposition of old and new. Nearby, where the paseo meets the Malecón, Havana's iconic oceanfront boulevard, the huge Hotel Paseo del Prado is slated to open for the big anniversary. An ungainly mass clad in a flashy mix of precast concrete, metal, and glass, the building squanders an extraordinary site that deserves much better. Cuban architects recognize that foreign capital is essential for these large projects but lament that their government doesn't set higher design standards, or sponsor competitions open to Cuban architects, who have been largely left out of the reshaping of their city. These newest examples of real-estate development are a discouraging preview of what could happen when Cuba opens to wider foreign investment in a post-embargo world.

The hundreds of new hotel rooms are coming online at a moment when planners aren’t sure that Havana's decrepit water and sewer systems can handle the added load. And with dwindling supplies of Venezuelan oil to fire power plants, Cubans fear the return of the rolling blackouts that plagued the country in the 1990s. Cuba has laudable goals for sustainable energy sourcing—mostly wind and solar—but is a long way from attaining them.

The tourist facilities now opening were initiated in the glow of the Obama rapprochement. But this past June, the Trump administration rescinded the popular “People to People” travel license, under which most American tours operated, and blocked U.S. cruise ships from docking on the island—and Trump has refused to nominate an ambassador to Cuba, even though diplomatic relations were restored in July 2015. (Ironically, before Trump’s run for president, the Trump Organization was scouting for resort sites in Cuba, in anticipation of Obama’s lifting the embargo.) Now nobody knows if there will be enough tourists to fill all the new hotels.

As usual, it is the ordinary people who suffer from such geopolitical maneuvers. When Raúl Castro became president in 2011, he introduced a number of economic reforms, including, most significantly, granting licenses to Cuban citizens to open certain private businesses. People were quick to start restaurants, guesthouses, and other enterprises catering to tourists. The pace of such autopropismo only accelerated with Obama’s Cuba policies, such as lifting the cap on remittances that Cuban- Americans could send to family on the island to finance these businesses.

The rise of a new entrepreneurial class in Cuba has been one of the most profound changes to Cuban society and, one would think, a development to be heralded by any U.S. government that seeks to steer Cuba away from hard-line socialism. But with the current American clampdown on travel, these budding capitalists are hurting, and Cuba’s experiment with free enterprise has been set back.

Another group that suffers is Cuba’s architects and designers. The practice of architecture is not on the list of permitted private enterprises—officially, all architects work for government agencies—but Cubans are endlessly adept at working around the rules. Many talented designers have built modest practices creating private restaurants, hostels, and art galleries, and renovating houses for the new business owners; either they obtain licenses as interior decorators or artists (which are permitted) or simply ignore the regulations as they moonlight from their official jobs. I met many young architects in Cuba who were wildly optimistic back when Obama made his historic visit to Cuba in March 2016 but are now deeply discouraged and want only to leave the island, which would accelerate the country’s deplorable brain drain.

Havana will put on a good face for its anniversary celebration, but it can’t mask the city’s current state of crisis. Gleaming new structures rise amid an urban fabric that is collapsing and with a national economy in precipitous decline, exacerbated by an administration in Washington that seems intent on its destruction. Havana has endured cycles of prosperity and peril for 500 years. The question now is how it will survive the immediate future.