“She was 17 years old, she walked the streets of Havana / Oh Cuba, your land is beautiful / One day a new sun will rise.”

So goes a sad, yet catchy song played for us by our tour guide, who wasn’t really a tour guide. (The song was in Spanish, but he insisted on translating for us, as he did for every song he played from his burned CD collection after I asked him what one line meant.) On a trip to Cuba last month, comparing the island to a nice girl driven to prostitution by desperate need seemed both vaguely rude and rather apt. With a 97 per cent literacy rate and a population stricken by poverty, Cuba truly fits the cliché-it’s a land of contradictions.

Take Bryant, our non-tour guide/translator. His real job was all-in-one hotel entertainer, serving as MC, singer, and guitar player for us tourists as we ate roast rabbit and lobster at the buffet. He was also croupier during the hotel’s “casino night” (no money was used-gambling was outlawed in Cuba long ago-but you could win a bottle of rum), and sometime dance instructor. Doing this earned him 40 convertible Cuban pesos (Cuba’s tourist currency) a month, 30 of which paid his rent.

“My ex-girlfriend always told me to leave Cuba, move to Canada. I said okay, maybe, I don’t know,” said Bryant, who spoke fine English and dreamed of being an actor. “But now I’m thinking it’s a good idea.”

With President Fidel Castro having temporarily left his duties for the first time since 1959 to battle a possibly fatal digestive illness, Cuba’s political situation seems uncertain. Havana, a city of decayed, once richly appointed Spanish-style homes and preserved fleets of 1950s American cars, feels poised on the brink of the future.

“Maybe something better is going to happen, maybe the same, who knows,” speculates Bryant. One thing is clear: Cubans have a filial affection for Castro, even though they wish they had better jobs. Some, like Eva, an 89-year-old Varadero woman (left), gratefully recall him as the man who ousted Batista.

Bryant, despite his long hours and his Superman T-shirt, is patriotic. He expresses his love for son, Cuba’s musical genre that blends African and Latin influences, and recites by heart 30 verses of a poem by the country’s best-loved writer, Jose Marti. Of course, everything could always be better: when I mention I might write about my experiences, he requests that I not use his full name, so that he can stay on the government’s good side. -SARAH BARMAK