Autoblog In Cuba: Introduction [w/video] [UPDATE]

UPDATE: As promised, Secretary of State John Kerry addressed a delegation of US an Cuban citizens this morning, capping his short remarks with the raising of the American flag on the embassy in Havana for the first time since 1961. Before today, a US secretary of state has not been on Cuban shores since 1945.

Kerry repeatedly lauded the opening of the Embassy as a promising first step for the return of normal US-Cuban relations. He noted that Presidents Obama and Raúl Castro "made a courageous decision" to stop being "prisoners of history" in the effort to restore normal diplomatic standing. Kerry also noted that it will still take an act of congress to discontinue the still intact trade embargo with the island nation. Something that, in a moment of timing that seems hardly accidental, Fidel Castro claims has cost Cuba "many millions of dollars."

Stay tuned next week for more of our Autoblog In Cuba series of features and videos.

For a guy that travels a lot, I'm pretty apprehensive about this latest trip to the airport. My quasi-OCD habit of checking my pocket for my passport – a trait that manifests whenever I travel abroad – has birthed some siblings in my sweating brain. I open the secret pocket in my laptop bag, running my hand over a bank envelope fat with several thousand dollars in fifties and twenties. Next to it lies a barely believable "international driver's license" that I picked up for $26 at AAA.

I switch on a nearly obsolete Garmin Nuvi, still unconvinced that the thing will hold a charge without respite from an in-car 12-volt charger, let alone pick up a GPS signal. It powers up, and delivers up a seemingly current map of Havana per my search.

I'm headed to Cuba to see what's good for drivers, and I have no Earthly idea what's going to happen when I land.

One Friday of this week, August 14th, US Secretary of State John Kerry will raise the American flag on our long-dormant embassy in Havana. Though the consulate has been open and operational since July 20, Kerry's re-inauguration of the building will mark first time since 1961 that Old Glory has waved over the cement tower. I'm arriving just before the advance teams from the world's biggest media outlets, and though I'll miss Kerry's historic visit, the reason for his coming is inexorably tied to mine.

Cuba has long been tantalizingly out of reach for American tourists. Travel exemptions have existed for journalists and students for some time, but average vacationers couldn't fly in on a whim. But now, with the Obama Administration loosening restrictions and warming up Cuban-American relations, there's more hope than ever that you may be able to visit Old Havana in the near future.

For the car-interested traveler, that's a fascinating prospect. Cuba's automotive culture is unlike any in the world. For better or worse, one legacy of the Castro-led country is a population of automobiles that is as diverse of origin as the individual cars are in terms of current condition. Dominated by heavily modified and often achingly beautiful classic metal from the 1940s and 1950s – both American-made and otherwise – the island also boasts Chinese and Russian cars that have never been sold on US shores. Of course, it's this national fleet of exotic vehicles that has me trading my Ann Arbor home for a Havana hotel room for a week; swapping the temperate Midwest for the Caribbean summer, all in search of car stories I can't find anywhere else.

Autoblog's beachhead in Cuba will be small but powerful. I'm traveling with our own video-making wunderkind, Christopher McGraw, as well as a guide who has made a career analyzing the relationship between our two countries.

Together, we're going to dissect the many ways you might travel around Cuba, for expediency or pleasure. How to choose the right taxi from the country's multi-layered conflagration of cabs. How to rent a car of your own to drive. How to find a chauffer-driven American dreamboat with which to tour in style. We'll also talk to the people and see the cars that make Cuba such a ripe spot for automotive enthusiasts to come and visit. I'm hoping we'll all learn that my pre-flight nervousness wasn't entirely justified.

If you haven't already, get a smattering of the Autoblog in Cuba action with our preview video above, or look below for an introduction to our guide, Senior Analyst at the National Security Archive, Peter Kornbluh. Then keep your browsers pointed at this site over the coming weeks, as we further explore the many-faceted glory of our long-estranged neighbors to the south.