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“In the name of God, the compassionate and merciful, welcome aboard.” With the stewardess’s pronouncement of these words, IranAir flight 744, to Caracas via Damascus, prepares for takeoff from Tehran’s Mehrabad airport.

Tehran and Caracas appear curious candidates for a direct air link. Tehran is the capital of a central Asian Islamic republic. Caracas is the capital of a South American “Bolivarian” republic (in honour of Simón Bolívar, serial vanquisher of South America’s Spanish imperial overlords).

Tehran is a drab, joyless, religiously straitened place whose people make what merry they dare behind the closed doors of private homes, and where alcohol is illegal (although, we learn, available, if you fall in with the wrong crowd). Caracas is a colourful, lively, unbuttoned barrio whose people are cheerful even when they’re not out drinking until sunrise. Tehran’s women use more material covering their hair than many Caraqueño women do covering their entire bodies.

The reason for the establishment of this bizarre route – the flight Monocle joined was the third such weekly trip – is what Iran and Venezuela have in common: brash, populist, ambitious presidents radiating a disdain for the United States, an erratic reverence for human rights, and a streak of what might be charitably described as eccentricity.

Iran’s Mahmoud Ahmadinejad threatens the destruction of a fellow member of the UN, and convenes covens of Holocaust deniers. Venezuela’s Hugo Chávez, more amiably if no less oddly, has, for much of his nine-year reign, hosted a weekly four-hour television programme, Alo Presidente, a good deal of which is devoted to the spirited abuse of his opponents. Ahmadinejad and Chávez have become friends of the enemy-of-my-enemy variety.

They have visited each other’s countries, embraced each other as revolutionaries and supported each other diplomatically: in 2005, Venezuela was the only country to oppose the IAEA’s resolution finding Iran’s atomic energy programme in violation of nuclear safeguards. Ahmadinejad has described Chávez as “a brother and a trenchmate”. Chávez has declared that Venezuela will “stand by Iran, at any time and under any condition”.

IranAir’s Caracas route is an emblem of this alliance. At this early stage, the link provokes bemusement among Tehran’s citizens – the response of every Tehrani I asked included some, if not all, of the words “crazy”, “political” and “bullshit”. That might not always be the case. The relationship between Ahmadinejad and Chávez may have begun as instinctive solidarity against a common, larger foe, but the two men also share stewardship of what are, from America’s perspective, infuriatingly bountiful resources. Iran has the third largest oil reserves on Earth, Venezuela the seventh. Iran owns the world’s second-biggest natural gas stores, Venezuela the ninth. According to Iranian media reports, the two countries have signed business agreements worth €1.87bn, with deals worth another €5.86bn pending.

Little of this wealth has, as yet, flowed to IranAir. Before the Ayatollah Khomeini’s Islamic revolution in 1979, the state-owned airline possessed a cache similar to that enjoyed by Emirates today. Its US routes were an early casualty of the revolution and sanctions imposed since have restricted the purchase of new aircraft.

For the passenger, this isn’t all bad. IranAir’s small fleet of ageing planes – the airline fields just 30-odd aircraft, ranging in size from Fokker 100s to 747s – have an air of charming retro gentility, their cabins decorated with silver and blue geometric shapes only otherwise seen on the shower curtains of mid-western American motels. And despite the strictures under which it operates, the airline has a superb safety record. It cannot be blamed for its worst disaster, the 1988 downing of an Airbus over the Persian Gulf by the USS Vincennes, with the loss of all 290 aboard.

Tehran’s Mehrabad International Airport does not exactly resemble the air hub of an oil-rich state. It’s a crumbling concrete 1970s headache, the only relief coming from the huge pallid and decrepit posters of Tehran, in which the choking city is presented as a calm urban oasis amid clumsily superimposed greenery (in fairness, it is anticipated that Mehrabad will eventually be entirely superseded by the newer Imam Khomeini International Airport, 30 kilometres south of Tehran). The shopping options are limited to a few electronic items and some baffling souvenirs – who buys an immense tapestry framed in gilded wood before getting on a plane? The security checks feature separate entrances for men and women.

IranAir’s customer service is also some way from being a model of brisk 21st-century efficiency. Every stage of our booking, confirmation and check-in is handled with truly fabulous incompetence – if Iran’s inflammatory nuclear programme is run like Iran’s state airline, the day that Ahmadinejad fulfils his threat to wipe Israel off the map could be a bad one for Poland. As the 747’s engines come alive, and the cabin loudspeakers quote sonorously from the Koran, and the cabin screens fill with pictures of Mecca, Caracas seems even further away than it is.

Despite the scoffing I’d heard in Tehran, it does initially look like the Caracas route has made some purchase on the local imagination. The plane is nearly full for our 05.00 departure, though few aboard look dressed for the South American sun: most of the passengers are elderly women in religiously observant costumes, men in traditional Arab garb, a noticeable proportion of blind and otherwise disabled.

We are granted plenty of time to consider the implications of this: with the passengers loaded, the Jumbo sits on the runway for three hours. There is not a word of explanation from the crew, nor the merest murmur of complaint from the passengers. The reason for the crowded plane becomes clear upon reaching Damascus. Most of the passengers shuffle off to customs: they’re Syrian pilgrims who’ve been visiting Muslim shrines in Iran. We spend a couple of hours in Damascus transit lounge, where the souvenir stalls sell Hizbollah T-shirts alongside Bashar al-Assad keyrings, and rejoin a much less populated flight.

Upon reaching the aircraft’s door, something finally goes right. The senior flight purser, Aryana Malekpour, perhaps recognising me and Monocle’s photographer as two men whose will to live is ebbing, ushers us into business class in the nose of the plane. There is only one other passenger in the section, a silver-haired cove of distinguished mien who turns out, when introductions are made, to be the Lebanese Consul to Venezuela.

Agreeably spacious though it is up forward, there’s plenty of room in the back, as well. Malekpour explains that there are only 60 passengers aboard the plane, and that at any rate this flight, given the fuel load necessary for the 14-hour haul to Caracas, could carry no more than 100.

After we reach cruising altitude, Malekpour introduces us to the plane. This 747 is called A4 Delta, and at 32 years it’s the oldest aircraft in IranAir’s fleet, though a recent overhaul is evident in the new pale-blue, purple and pink paisley upholstery on the seats. We also meet the crew, a few of whom, the saintly Malekpour included, have been with IranAir as long as A4 Delta.

When, to my considerable surprise, I’m led upstairs and on to the flight deck, I sit next to flight engineer Mohammed Reza Rafat. I ask him to outline the difference between the pre-revolutionary IranAir of the Shah’s Iran, and the IranAir of the post-1979 Islamic Republic.

“Well, we don’t serve alcohol any more,” he grins. “And, of course, the female crew have had to cover up.” While IranAir’s male staff sport generic, vaguely military black and white uniforms, IranAir’s women are shrouded in an elaborate, but not ungraceful, dark blue and gold headdress. “Also,” says Rafat, “most of the men stopped wearing ties.”

Khomeini famously objected to these on the grounds that they were western. “I don’t know,” says Rafat, adjusting the newspaper blocking the sunlight beaming into the cockpit’s port window. The captain seems to ignore this ruling.

In polar contrast to the ground-based portion of IranAir, their flight crews are courteous, efficient, proud of their airline and their country and cheerfully talkative. All, that is, except one, who is the reason it would be irresponsible to quote the others too liberally (a few, indeed, quietly ask me not to, though aside from some wistful remembrance of IranAir’s 1970s golden age, not one of them says anything that could be regarded as disloyal to their country or their airline). The only hostility we encounter from the crew is from the captain, James Farrahi, who initially declines to be photographed on the grounds that he “doesn’t like the English” who he blames for “screwing the world up with their conspiracies”. But perhaps because we bite our tongue, we manage to depart friends.

In economy class, there are a few Syrian contract labourers with building jobs to go to, but most are middle-class Iranian professionals, enjoying Ahmadinejad’s encouragement of business links with Venezuela, if not always in terms he might appreciate (“You ask why this flight is happening?” says one. “Because our two countries have something in common: crazy presidents.”) Kayvan, a thirtysomething businessman travelling to work on a project to establish a plant to build a Venezuelan version of the Iranian Samand car – and not, it should be stressed, the utterer of the previous quote – paid €1,128 for his return ticket. It’s only a little cheaper, he says, than the Lufthansa flight via Frankfurt, but he likes the space on board. “There’s a nice atmosphere,” he says.

He’s right. Without the usual mobs, and the consequently hassled and pressurised crew, people meander and chat – or, if so inclined, visit the on-board prayer room, in which a screen carries a computer graphic of the plane indicating the direction of Mecca. There is little else by way of distraction. IranAir offers no in-flight games, no seat-back movies, only a couple of Iranian family comedies on the cabin screens, alternating with the SkyMap chronicling of our languid progress across the Atlantic, and no mood-altering substance stronger than Iran’s Coca-Cola substitute Zam Zam (the halal food’s pretty good though – buttery Iranian rice with meat and vegetables). The inflight magazine, Homa (named for the griffin-like creature of Persian mythology which also serves as IranAir’s tailfin motif), is an unriveting melange of dull travel guide hackery.

Strangely, but rather delightfully, this lack of the usual amusements proves an unalloyed blessing. Along with the jarring juxtaposition of departure point and arrival destination, the absence of vacuous distractions help promote a rare feeling of travel as a genuine adventure – and, as this unlikely journey around half the globe unfurls, a renewed appreciation of the miracle of flight. It is astonishing that we’d rather watch Friends than the tops of clouds, or take in Richard Curtis movies over the sun dipping behind the Cordillera de la Costa mountains that shield Caracas from the sea. The relationship between Iran and Venezuela may strike many as worrisome, but it has produced one of the great romantic, quixotic, travel-for-the-silly-sake-of-it experiences presently available.

Caracas’s airport, like Venezuela’s currency and any number of Venezuelan locations, is named after Simón Bolívar. It is, in every respect, a long way from Tehran: new, clean, spacious, as much like a shopping mall with a runway attached as any major airport in Europe, and the large numbers of armed, uniformed men are at least friendly.

For flight ir744’s pair of infidel passengers, Caracas also offers the welcome prospect of a restorative beer or several. Mighty forces appear determined to torment us further, however. The bright lights of Caracas, in theory just 21km over the hills, are in fact two and a half hours away, at the end of a traffic jam of such hilarious length that it could almost have been imported from Tehran.

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