The American embargo on Cuba has spanned 48 years—a lifetime for many Cubans, and nearly all of Fidel Castro’s tenure as Maximum Leader. Now that Castro, 81 and ailing, has officially retired, the embargo’s end may be near. Some think Fidel’s brother Raúl (assuming he successfully consolidates power) might free Cuba’s economy and allow private investment.

U.S. business interests have been eagerly awaiting Castro’s departure—one way or another—for years. Otto Reich, who worked within the Bush administration on post-Castro planning and other Cuba issues from 2001 to 2004, says that for a time, after the Cold War ended, construction companies were pre-positioning materials in Florida warehouses in anticipation of a Cuban counterrevolution. Bulldozers and cranes waited to cross the Florida Straits and start building condos and shopping centers.

CLICK THE IMAGE ABOVE to enlarge

Optimists envision post-embargo Havana as a capitalist paradise, restored to glory by the healing powers of the free market. But an invasion of developers might have its drawbacks as well—particularly for a city with Havana’s storied history and distinctive architecture.

New residents and tourists will strain resources. Joseph L. Scarpaci, an urban geographer at Virginia Tech, says Havana already shudders under its population’s demands. It is plagued by brownouts, even though air-conditioning is still rare. Fresh water is scarce, and human waste flows untreated into the sea.

Nicolás Quintana, 82, a Cuban American architect heading a Florida International University project for Havana’s post-Castro future, likens the city’s condition to that of postwar Warsaw or, less fancifully, post-Zhivkov Sofia. For decades, the island’s construction materials have gone to the military, and as a result, Havana is crumbling.

Quintana dreams of returning in time to save Havana from collapse but before unchecked growth robs the city of its character. His project, an initiative with support from Cuban exiles—among them economists, ecologists, and urban planners—calls for preserving the city’s narrow streets and short blocks, and encouraging concentrated vertical development, creating something like “a latin­ized Paris.”

Whenever Havana opens, it will face a clash of interests—between developers and preservationists, and between moneyed exiles and poor habaneros. This map, based loosely on the visions of Quintana, Cuban American economist Jorge Sanguinetty, and others who’ve been eager for Castro’s end, depicts what might follow, and how the city might be rebuilt.