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In the bustling, open-air mausoleum of antique cars, crumbling colonial buildings and obsolete Soviet-era politics that is Havana, the streets are devoid of garbage. When you forget your camera on the table of a sidewalk café, it's still there when you return half an hour later. Everyone looks happy and neatly-dressed — and with and free university education, even your waiter turns out to be an orthopedic surgeon.

After a few minutes of wary conversation, though, ask him why he is a waiter.

“Because I can't support my family on twenty-five dollars a month.”

“What do you think of Fidel?”

His voice drops. “We don't talk about the bearded one. There are plainclothes police everywhere.”

You tell him what a beautiful city he has: no crime, clean streets.

He gives you a sad shrug. “Democracy is messy.”

Havana is worth learning about, but most Canadians come to Cuba on packaged vacations and only visit the capital for a few hours. The best way to get a basic sense of Castro's strange society is to spend a few days in a grand old hotel like the Nacional or El Presidente and make the rounds with a local guide like Alejandro Trelles Shaw.

Like many Cubans, Alejandro works the angles to get by, and one of his enterprises is offering visitors a no-guff introduction to the real Havana. For 29 years, the avuncular Alejandro worked as a field agent for the Ministry of the Interior (Cuba's version of the KGB), and although he's long retired, he still packs his nine when he feels the evening warrants it. “Some guys want me to take them to wild bars,” he says. “Cuban women are very beautiful and if guys want me to get them women I'll do it. But I don't enjoy it. I prefer to go out with smart people to a nice restaurant, talk to them about Cuban culture and history, take them out and show them my city.”

Alejandro will pick you up at the door of your hotel in his old Lada, take you to the cobblestone streets of old Havana, or to little shops where they hand-roll the best cigars in the world, or to exclusive spots like El Aljibe, a palm-fringed restaurant in Miramar where arriving with him gets you ushered past the lineup to the best table in the house.

Seated with your group, expelling great plumes of aromatic cigar smoke, Alejandro comes into his own as a raconteur. He's been married three times and has travelled the world. He grew up in a wealthy family under Batista's regime, and was young enough to change his spots and become a field agent when Fidel and Che took over.

Working for the Ministry, Alejandro shadowed CIA-funded student groups at the university in Havana. Castro would sometimes show up on campus and drink with the students and professors until 3 a.m.

“One night we were sitting outside and this owl kept flying by. The Commander was seized by the idea to shoot it with the machine gun. He was always the last one to tire. He loved staying up all night.”

Unlike most Cuban government officials, Alejandro speaks perfect English and ended up working for Fidel as a translator on trips abroad. Castro's face would darken when Alejandro disagreed with him. “I'd say, ‘But Commander, you were the one who taught me to speak up for myself!'”

After dinner, Alejandro saunters through the darkness with a Churchillian cigar wedged in his mouth. He's not one to mince words, but he shrugs off any suggestion that he'll annoy someone with his comments about politics. “I'm just an old man. They don't care about me.”

When he drops you off at your hotel, Alejandro doesn't ask for money. Discussion of payment is beneath him. But he's raising a 15 year-old daughter by himself and can use whatever you think the outing was worth. If you press him, he'll grudgingly admit there's one thing he could use the next time you're back in Havana: “A Hewlett Packard model 28 printer cartridge, the coloured kind. Computer supplies are impossible to get down here.”

Contact Alejandro Trelles Shaw at 53 (7) 892-8016 or 53 (7) 830-1856

Special to The Globe and Mail