All we really wanted was a smoke. Yet here we were in Havana, the traditional capital of cigars, not puffing on habaneros but marching through the Museum of the Revolution. The once-ornate chambers in the former presidential palace are now occupied by scenes from the Twenty-sixth of July Movement’s glory days; guards sit reading as tourists file past dim glass cases containing faded manifestos and bloodstained martyrs’ garments.¹ The museum interrupts its chronicle of socialist triumph—in both Spanish and English—with periodic detours through gift shops tendering books, flags, DVDs, and T-shirts. For a country where there’s almost nothing to buy, Cuba has a lot on sale.

The museum is one of the few places in Havana where a smoking ban is enforced, but the revolution, it’s pretty clear, was permitido fumar. As we saluted Che (dozens of photos suggested that his Montecristos might have done him in had the CIA not beaten them to it), we had to admit that most of the reasons we’d given for coming to Cuba, including to ourselves, were bullshit. We’d declared that we wanted to look into how a New World leaf regarded by Renaissance Europeans as “negro stuff” could, when rolled into pocket-size torpedoes, become a universal status symbol. We wondered how this capitalist icon was holding up on the fiftieth anniversary of the revolutionary state that produced it. Here was an exploitable irony—or so we told editors, friends, and companions by way of excuse. There were plenty of other reasons to visit Cuba: the lefty pilgrimage, the easy feeling of subversion, the crumbling elegance, and, of course, the escape, since what happens in Cuba is more likely to stay put than what happens in Vegas. Not to mention the prospect that Obama might any day lift the travel ban and make it less fun to go. But really what we wanted was a smoke—an exquisite bath in the fog from the world’s iconic cigar without having to break the law, break the bank, or break up with lovers bleating cancer, cancer or braying about stinking up the house. Why was it turning out to be so hard?

It’s not that there weren’t plenty of cigars around. They were in the mouths of Che-T-shirted hippie-wannabes in old Havana and between the stubby fingers of sussurant Russians at the Ambos Mundos hotel, where Hemingway is supposed to have knocked back fourteen daiquiris a day. They were on offer in gift shops and, sketchily, on the street. Where they weren’t was in the mouths of...