Flirting with the Enemy: The Changing Face of Travel to Cuba

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For travelers who are personally acquainted, Cuba’s 21st century brand of tropical Marxism remains as ambivalent as it is alluring: a Caribbean party island where 1950s American cars splutter alongside horse-drawn carriages and sleek art deco towers flank crumbling colonial mansions emblazoned with revolutionary iconography. The cigars are the finest in the world, the rum flows freely, music electrifies body and mind — it comes as no surprise that Cuba had such a hold on Ernest Hemingway.

While many Cubans still view their national identity through the prism of a David-and-Goliath struggle against the evil empire of the United States and continue to revere Che as a beret-clad Messiah, Raúl Castro is keenly aware that the utopian ideals of the Revolution cannot eternally bolster the country’s stagnating economy.

When it comes to ideologues, self preservation is a potent economic force. When Cuba’s communist sidekicks collapsed like dominoes in the 1990s, the so-called Special Period transformed Havana from a place with one of the highest standards of living in Latin America into a medieval landscape, and the regime’s ideological foundations –cradle-to-grave education, housing, and health care for all — began to crumble along with the capital city’s colonial treasures.

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