In search of hidden Porsche gems: A four-day road trip worthy of the silver screen. Frosty relations between the United States and Cuba have finally thawed after more than half a century. Yet in spite of the rapprochement, Cuba remains a mystery. A harmless appointment at the Porsche Club in Havana almost turns into a spy thriller.

Havana, 1962. Prologue. The Porsche armada rolls past the walls of the Malecón. The 1.5-liter engines of the 356s leave the 3-liter engines from Italy and the 5-liter behemoths from the United States in the dust. The crowd gawks and cheers, celebrating the small, agile race cars from Germany. In the end, two Porsche 356 Speedster GTs score a sensational one-two finish in the last international auto race held in Cuba.

2016. Cuba’s isolation is a thing of the past; the embargo is coming to an end. Yet Cuba’s capital Havana still seems like a place that time has forgotten. There’s a thin line between desperation and hope here. The search for the island’s Porsche treasures becomes an exercise in patience, with tight-lipped informants, secretive messages, long drives, locked steel gates, and bizarre surprises.

The putative Porsche Club Cuba no longer exists. The names of the owners of the few, well-hidden models from Zuffenhausen are guarded like state secrets, yet giving up is not an option. The task involves driving hundreds of miles across the country, shaking countless hands, and conjuring up smiles in spite of growing exhaustion: ¡Todo bien! It’s all good! It’s a grueling roller coaster of emotions. On the one hand, there is the persistent reticence of the people; on the other, the vibrant beauty of Havana, a city full of picturesque colors and delightful caravans of quaint old cars. Almost all of them are American, with the odd Lada thrown in. Not a single Porsche.

The first clue leads to a decorative iron gate. The missing classic Porsche models are allegedly lurking somewhere behind it. Alas, Orlando Morales waves us off. Can we come in? Not now. Maybe later, maybe not at all. Orlando keeps mum. The 77-year-old is our first major contact. He is a man with the angular, often completely expressionless face of someone who has seen it all and is not about to lose his cool now. The gate stays closed, and the reality of a real-life Porsche vehicle remains a mere hope. Orlando takes the edge off somewhat by mentioning a collection of black-and-white photos of the grandiose Porsche race cars from the 1950s. Photos are all well and good, but our quest is to find the actual cars that survived. Will the closed gates open for us? On the first evening, there’s just a faint hope.

The next day, however, that hope becomes a bit more tangible, in the form of Maxy Ramos and his 1952 Plymouth Cranbrook. Maxy explains that he’s actually a veterinarian. But he doesn’t have a job as a vet—just his grandfather’s old Plymouth. The car, with its leather-upholstered backseat, is his life. He uses it to earn the pesos he needs to support his wife and seven-month-old son. The aging sedan enjoys Maxy’s full attention.

He artfully dodges every pothole in the crumbling asphalt, implores us to close the doors with care, and—in the strongest possible terms—curses the salty spray of the Atlantic waves that crash over the walls of the Malecón promenade and attack the body of his taxi. Every day, he and his freshly polished car are found in front of the hotel. Maxy is our human navigation system in our quest to find those with an automotive passion that is deeply felt and shared even in Cuba: namely, that select group of people who love Porsches.

Once again, it is the poker-faced Orlando Morales who ultimately—aided by Manuel García Fernández and Alberto Gutiérrez Alonso—leads the way to the last existing Porsche models on this Caribbean island. Orlando is regarded as Cuba’s automotive archivist. He has a directory of all legally imported vehicles. If anyone knows anything about the location of any cars from far-off Alemania, he does.

In his small apartment on the Plaza de la Revolución, he spreads out some black-and-white photos of Cuban Porsches. On the windowsill, tiny birds pick at the grains of rice that Orlando sets out for them each morning. One picture shows the memorable face of the Porsche racing director Huschke von Hanstein. Surprisingly, in Cuba he joined the fray himself and drove a Porsche 718 RSK for 65 laps in the Gran Premio Libertad, the Cuban Grand Prix, in 1960.

Another photograph shows Carroll Shelby, creator of the AC Cobra, behind the wheel of a Porsche 550. Other racing legends such as Graf Berghe von Trips, Edgar Barth, and Stirling Moss are likewise immortalized in the yellowed images. Then Orlando points to one very special face: the master of all masters, Juan Manuel Fangio. The picture was taken on February 22, 1958, one day before his spectacular kidnapping.

1958. It was that time in Cuban history when President Fulgencio Batista was endeavoring to turn Cuba into an El Dorado for the international jet set. Havana was to become a second Las Vegas. And to draw in the rich and famous, attractions were necessary. Batista managed to ensure that the international racing scene would find its way to the Cuban capital. But while high-society types were cavorting around Havana in American limousines, trouble was stirring in the mountains. The group of bearded revolutionaries formed around Fidel Castro and Che Guevara were just waiting for the right moment to overthrow the Batista regime. The rebels took advantage of the 1958 Cuban Grand Prix to kidnap the world champion Maserati driver Juan Manuel Fangio. They would hold him for nearly 30 hours.

2016. Our focus turns to Porsche’s present in Cuba. There is a Porsche Club Cuba in name only; its founding in 2003 did not lead to an actual revival. Under the still-attentive eyes of the authorities, finding true Porsche enthusiasm is more difficult than anticipated.

Supposed or indeed real luxury goods are still kept under wraps in spite of the new policy of openness that has begun to emerge. The morbid charm of bygone riches still defines the picture of modern Cuba. The buildings and infrastructure of the city continue to deteriorate slowly before the eyes of its inhabitants. A walk through the glorious Havana of old provides ample proof of that. One may peer into a historic library or a crowded bar, and then, just next door, encounter a huge hole where a structure once stood and a pile of debris left on the street. The bare frame of a building lies exposed with an intact stairway hinting at the life that once filled the space. Pedestrians give a wide berth to such scenes. Havana keeps moving and yet stands still.

Orlando Morales reveals that during his time as an active race-car driver, he once drove a Porsche 550 A Spyder himself—an experience that is as alive for him today as it was then. “It must have been 1961. At that time, I was used to driving only heavy, big­engined American models. The lightweight Porsche felt like a combination of a jet airplane and a go-kart.”

Although Orlando didn’t manage to qualify for the main field, you can still sense his euphoria half a century later: “I’ll never forget that day.” He seems electrified; his energy is back, and the aging archivist of Cuban automotive history wants to help smoke out the Porsche vehicles of today—the ones that have survived.

The few car fanatics in Cuba form a well-connected network, and as soon as we’ve won Orlando’s confidence, the door opens to Manuel García Fernández and Alberto Gutiérrez Alonso, who is president of the Club de Autos Clásicos y Antiguos. At first, however, we just exchange telephone numbers and business cards. Once again, waiting is the name of the game. The network is working its magic.

The next day, Manuel García names the meeting spot: the old Castrol Villa. Movement at last! Maxy’s Plymouth starts up without hesitation. He’s got his sunglasses on and “Guantanamera,” the island’s song, on the car’s radio: “I am an honest man from where the palm tree grows, and before I die, I want to share the verses of my soul.” The lyrics originally penned by Cuba’s national hero José Martí describe the Cuban soul, an enigmatic mix of macabre longings and joie de vivre.

We drive past the legendary Hotel Nacional, an aging palace looking out over the sea. Again and again, surges of seawater crash over the Malecón in gigantic waves. Clichés are a reality of everyday life here.

Manuel and Alberto drive ahead toward Miramar and Punta Brava. The taxi fills with the sound of “Riders on the Storm” by The Doors: “Into this world we’re thrown, like a dog without a bone.”

We drive past the architectural sensations of the 1950s, which are somewhere between grandiose and grotesque, then an amusement park that’s been out of operation for years. After countless miles of astonishing sights, we again encounter the commonplace: a locked steel gate. To guard against the overly curious, thick glass shards have been applied to the sandstone walls on either side. Once again, the magic word is wait. If there’s anything one can be absolutely sure of in Cuba, it is the inevitability of having one’s patience tested.

Finally, the heavy gate swings open. The path leads through an unkempt garden to a Porsche 356 C that has evidently been parked there for ages. At last! Under a blanket of coconut fibers, the wine-red coupe is taking a nap. The four-cylinder engine is no longer in its place, and the dismantled doors are stacked up in the passenger compartment. It’s a sad sight, and yet the first Porsche is balm for the soul.

The holes where the taillights once were are noticeably larger than on the original. Its owner, who now lives in Florida, was evidently obliged to replace them with the blocky taillights from a Russian Lada. Alberto is in a hurry. The next Porsche!

What, already? We wait four days to encounter a single sports car from Stuttgart, and now, within 30 minutes, we’ve got two on the line? Alberto can’t wait. Time to move. Manuel bids farewell as Alberto hops in the Plymouth. We hit the road. Once again, an iron gate blocks the way. Cuidado hay perro, says a weathered sign. Beware of the dog. There will be no biting here. In the distance, hidden behind some palm trees, is the silver silhouette of a Porsche 356. The coupe is protected by a carport. It’s uncanny how naturally it seems to sit there and in what relatively good condition it’s in.

Alberto approaches the gate, plucks a ripe avocado as he passes a tree, and exchanges a few quick sentences with the gardener emerging from the thicket. A brief dialogue, followed by Alberto’s rapid-fire command, or rather more like marching orders: “Five minutes! Not more.”

The gate opens, and we follow a labyrinthine footpath across the grounds belonging to a former “supporter of the revolution,” as Alberto puts it. Three more minutes. The car is an early Porsche-Reutter production of the Porsche 356, as its type plate on the A-pillar reveals. The rear end of the body is jacked up to take the weight off of the axles.

One minute. I glance through the open door of a surprisingly modern interior. The Recaro seats couldn’t be more than 20 years old. But before I even get around to the first question, our time has expired. Who owns this little gem? No answer. “Maybe next time,” says Alberto, “but not today, not now.” Somewhere, there’s a phantom with an affinity for Porsches.

On the way back to the city, the phone rings. Ernesto Rodríguez, cofounder of the once-vital Porsche Club Cuba, is on the other end of the line: “Come back to Havana, quick!” Two roadworthy Porsche treasures have turned up. Where have they come from so suddenly? To whom do they belong? There is no answer to these questions either. Of course not.

Two 356s could scarcely be more different than this duo. One is beige, a flawless specimen, model year 1957. Fresh and gussied up as if in its Sunday best. The other one looks more like a patchwork rug, a mosaic-style 356 made up of various blue tones. Model year 1953, with the characteristic center-creased windshield, or Knickscheibe. Time has taken its toll.