I bought my tickets almost the minute that Southwest Airlines announced direct service between Tampa, my home base, and Havana, Cuba.

Now, the day of travel is finally here, and after just seventy minutes in the air, the plane is dipping through early morning clouds for a stunning sunrise reveal on the lush Cuban countryside.  Havana’s Jose Marti International Airport has yet to get the memo that Cuba is an up-and-coming travel destination…  It looks much the same as it must have at the dawn of aviation, little more than a crude collection of salmon-colored buildings, not even equipped with a single jet bridge.  The couple of American jets park outside the international terminal the way mothers pull their SUVs to the curb in carline, as passengers cross open tarmac to collect passport stamps.

Largely because of the longstanding American embargo, Cuba is perpetually short of foreign cash reserves.  The government has borrowed a page from Chuck E Cheese, inventing a token currency – the convertible unit – for use only in transactions with tourists.  This convertible unit has an exchange rate pegged artificially high to the dollar, and on top of that, every item purchased with the convertible has an inflated tourist price.  So, a half sandwich in a government restaurant ends up costing about $10 – but you can do a lot better than that in the private restaurants that have been allowed to flourish under more recent reforms.  I’ve been meaning to lose weight anyway.

But even as I wait for more than half an hour, watching as the women at the exchange counter run every convertible unit they will need for the day’s business through a counting machine, even as they pretend to ignore the growing line of foreigners behind me, confused as to why the worker at an exchange counter that is supposed to be open 24 hours a day is telling us in sharp Spanish that they aren’t open yet, it is hard to be too upset.  This elaborate game of gauging tourists is not an ordinary one – it is a rational response to an embargo that by all rights should have been lifted decades ago, if it should ever have existed in the first place.  It is the penance of the privileged American tourist for the sins of his country.

From the shambolic countryside surrounding the airport to the crumbling facades of Old Havana, this country is shockingly, strikingly poor.  I spend most of the day walking the Malecon, people-watching and being watched, checking out the monumental architecture, most of which dates to the pre-Revolution period.  Much is made of the ancient American cars that prowl the streets as if Batista were about to fall any day now.  It is a world wonder that these things still run, let alone look so good for their age.  Less is said about the sorry state of repair of everything else in this country, from buildings to roads.  Some buildings are clearly occupied, and yet have front doors that look more like the entrance to giant rat’s nests – gnawed and uneven, and I can’t even imagine how it happened except that maybe these buildings were literally blown open in the 1959 revolution and still haven’t been repaired.

That’s speculation, but even for a 500 year-old city, this place looks old.

The smug among my countrymen will say this is proof that socialism, in Cuba or anywhere, doesn’t work.  And maybe it doesn’t.  But I wonder about all of the effort that my country has made to ensure that that was a self-fulfilling prophesy, from the embargo to its one-dry-foot immigration policy, favoring those Cubans with the means or the health or the tenacity to leave.  It’s true that Castro wanted many of those same people out, but it’s also true that a great deal of his regime’s hardest line was a direct, embattled response to America’s efforts to delegitimize and undermine Cuba.

This is a country so deprived, for god’s sake, that they’re selling Big Chunky Kit-Kats out of a jeweler’s locked display case.  That is one of the single most intense things I’ve seen, and this is the twenty-fourth country I’ve visited in my life.  It is telling, in as much as it points to the degree to which the Cuban people, like people almost everywhere, are just caught in the middle of bigger, more abstract pissing contests courtesy of men whose principles are more important to them than their obligations to their fellow man.

These people just want a piece of chocolate, but Senator Marco Rubio – and half a dozen American presidents – want to make sure that Fidel pays for his insouciance, even from beyond the grave.

So I’m thinking these kinds of thoughts all day, and now I’m sitting on the Malecon as the sun is setting.  I have a small sketch book with me given to me by a student, and I’ve vowed to put it to use on this trip.  I’m sketching the decaying seawall, emulating its rough contours with slashed of my pen on paper, when suddenly a Cuban man, about my age, smoking a cigarette, and carrying an acoustic guitar speaks from behind me.

He compliments my talent, flattering me, I think, before he tries to sell me a performance with his guitar.  I’m guarded and a bit aloof, I’m ashamed to admit.  I thank him and go back to my drawing.

He lingers, complimenting me a second time, asking, “Are you a professional?”

I stop, but only talk to him over my shoulder.  “I’m just an amateur.  But I’m inspired – your city is very beautiful.”

“This city may be beautiful to you, my friend, but not to me.  Life here is hard.  Very hard.  I play this guitar for my living, and thankfully since two years ago, since Obama, there are many American tourists coming.”

I again feel him winding up for the pitch.  He is going to ask to play for me, like half a dozen others have offered to sell me cigars, classic car rides, women…

Instead he asks me about my life in Florida.  My wife and daughter come up, and he talks about how badly he and his wife would like a son – not now, but when the time is right.

He offers his hand, “Take care my friend.”

I take his hand, respond in kind, and offer my name, the way one does at the end of these fleeting conversations.

“It was a pleasure to meet you.  My name’s Fidel,” he says with a knowing smirk before he turns to walk away.

And just like that, a human connection.