Legendary journeys

Leaning out of the open-air observation car of the Eastern and Oriental Express is all about timing: Palm fronds and low-hanging trees thwack the train as it passes through the jungle. Impromptu railway bridges – closer to the carriages than you'd expect – are frequent. But these are mere obstacles, part of the game. You can't help but stick out your neck to breathe in the thick air of this heavy, green world.

Taking one of the world's legendary train journeys, about 2,000 kilometres from Singapore to Bangkok in historic rail cars fitted out like a five-star hotel, passengers will spend hours this way – watching the tracks roll endlessly behind the teak-decked caboose, a cigar and a glass of whisky in hand as the rubber plantations and rice paddies slip away.

Tales of travel in this region usually involve a degree of struggle – the choking traffic in Bangkok, the withering heat of Singapore, absurd queues at border posts in between. But E&O Express passengers have none of that. We sip drinks in the air conditioning while stewards ensure the passports are stamped. This is the legendary hospitality of Belmond, which runs luxury trains around the world, including the Venice Simplon-Orient-Express in Europe. Belmond began running this route in 1993, creating the first luxury train in Southeast Asia. It remains the only one.

But the only difficulty on board the Eastern and Oriental Express is the occasional argument between the train and the century-old tracks beneath it, sending laughing guests and wine glasses tumbling. Then it's back to refills in the bar car and admiring long stretches of gorgeous countryside in good company. If our tuxedoed manager doesn't point out that the train is passing through a civil war zone, where insurgency has meant the area has been mostly devoid of tourists since 2004, well, who's to blame him.

The contrast is likely lost on the mostly North American passengers revelling in their once-in-a-lifetime splurge.

The trip starts with the Sling. In a dining room adjacent to the Long Bar at Singapore's majestic Raffles Hotel, three dozen overheated travellers sit in near silence as Belmond's local staff flit about checking details. Everyone looks relieved to be out of the heat and excited for what comes next, though what comes next is the least luxurious and interesting part of the trip.

We're soon piled into minivans, handed bottled water and shuttled to the border with Malaysia. Trains no longer use Singapore's art deco Tanjong Pagar Station since it became a national monument in 2011, so we're heading through the city to Woodlands Checkpoint on the northern edge of the city state. The 40-minute shuttle ride has been styled as informative, part of the excursions and tours that paper over the technical challenges of running a long-distance train. A friendly Belmond employee describes Singapore as it passes, but the details are dull: Here's an MRT (rapid transit) station, here's Singapore's only nature reserve, here's a water tower, here's another pile of ugly flats.

But waiting beside the platform at Woodlands is the most beautiful train in the world. Dark green and cream coloured, 20-carriages long. The E&O shimmers faintly in the afternoon sun. A smiling staffer ushers us through polished teak hallways to our cabin, a bunk-bed affair with muted fabrics and the same dark wood of the hallways, a bottle of wine and a packet of the history of the railways sitting on the fold-out table. Our luggage, spirited from us at Raffles, is waiting, tucked away, and the cabin steward explains the simple, comfortable room and how we can reach him – 24 hours a day, he insists – before he whisks off to greet more guests. Before long, the train lurches northward, beginning its crawl toward Bangkok. You're forced to move at its speed. And the slowness takes a while to work its way in.

Day 1

Exploring the train – difficult when other couples have the same idea since nowhere in the halls can two people pass one another – we find three restaurant cars, two bar cars, a lounge, a library, an inexplicable souvenir shop and the glorious outdoor observation car. In short, there are countless places to sit to watch Malaysia quietly roll past. There's no WiFi, so there's no temptation to chronicle the trip instead of enjoying it. On the E&O Express, you talk. This begins as darkness starts to fall on the Malay Peninsula. The rear bar car fills up, the train's manager, impeccably tuxedoed and French accented, offers a glass of champagne while we wait for our reservation in the dining car, and a din settles on the room as we chat.

This isn't a trip for solitude. At each lunch and dinner served in the restaurant cars (breakfast is served in your cabin) you're placed with a new pair of travellers at the whim of the restaurant manager.

The train has a dress code for dinner: The pamphlet we found in our cabin suggests a shirt and tie for men and "the equivalent for ladies." Some passengers truly embrace the setting and go full formal. A fine three-course meal is served in the rocking carriage and the clinking and rattle of the dishes provide a backdrop for friendly conversation. We close the restaurant car down over refill after refill of wine while chatting with our dinner-mates, whom we invite to stay with us in Istanbul, where we live (by the end of the trip we've extended this invitation several times). There's nowhere else to be, so the night goes on with easy conversation and getting to know the others before stumbling back to the cabin to be rocked to sleep by the cadence of the tracks.

Day 2

Shortly after breakfast on the second day, the train needs to refill its water tanks. The need to balance dull maintenance and adhere to rail schedules means passengers are shuffled off into one of Malaysia's regional capitals, Kuala Kangsar. But the two-hour tour is painful. You'll see more interesting mosques almost anywhere else in Malaysia and better museums everywhere else in the world. Stay on the train and read.

Back on board, the journey resumes its familiar casual pace. The day is ours for lounging, drinking and chatting. The constant need to interact with other passengers could be tedious if not for the interesting mix of those drawn to this train: journalists, university professors, retirees and train enthusiasts, all pretty well drunk by lunch.

After a brief stop at the Thai border – the formalities of which are handled by the train staff so that you don't even need to stand up – the journey hits its stride crossing through the narrow southern provinces of Thailand. The contrast with Malaysia is stark. Not only is the landscape more stunning, but each passing village, station, road crossing and farm reveals the inherent warmth of Thai people. Gone are Malaysia's frowning suburbanites, replaced with the smiles and shouted hellos of families of four teetering on a Moped or the scrawny farmer lazily pacing after his equally lazy cows. But this smiling countryside is a war zone; the provinces on the Malaysian border are home to regular bombs and outbursts of gunfire between the Thai military and local militias. Foreign tourists are scarce except those passing through. Few stop and our train certainly doesn't.

From the observation car, it's impossible to fathom that violence erupts regularly here. It's less difficult to understand the following day.

Day 3

While enjoying a breakfast of fresh orange juice, croissants and yogurt in our cabin, Valentin, the manager, announces the next stop on the program: the Death Railway.

During the Japanese occupation of most of Southeast Asia in the Second World War, hundreds of thousands of enslaved Burmese, Malaysian and Indonesian workers were joined by British, American, Dutch and Australian prisoners of war to build a railway from Bangkok to Rangoon in Burma (now Yangon, Myanmar). The E&O Express stops at, and then crosses, the iron bridge over the river made famous by the 1957 film, The Bridge Over the River Kwai.

The tour around the bridge and to the nearby Thai-Burma Railway Centre in Kanchanaburi are excellent, but the contrast between the elegant, expensive tourist train that costs thousands of dollars to ride and the bridge that cost thousands of lives to construct is lost somewhat. Instead, tourists eagerly clamber to take photos of the train as it rests at the bridge, a bubble of modern glamour landed on a wartime skeleton.

The heaviness of the museum lingers in my mind and is joined before long with the heaviness of realizing our last stop approaches. When Valentin announces delays at the junctions, the sense of relief among the passengers is palpable. No one wants to leave. But the bubble, if not bursting outright, is slowly hemorrhaging its rarefied air. Now come the practical matters of paying an astronomical bar bill and trying to repack in a room that suddenly feels tiny.

And all at once Bangkok Central Station is upon you; the stewards haggle for your taxi, while the friends you've made over the past 48 hours disperse into the honking madness.

IF YOU GO

The E&O Express runs two regular schedules: two nights from Singapore to Bangkok from $2,280 (U.S.) or three nights from Bangkok to Singapore, from $2,690 a person, including all meals and side tours (excluding extras such as spa treatments in the train library). Drinks, however, are not included. A glass of wine or a small bottle of domestic beer runs $10, cocktails are between $14 to 20. Bottles of wine are $55, or more for vintages.

The north-to-south trip gives you an extra night on board for the same price and the benefit of travelling along the Gulf of Thailand during daylight hours.

Belmond also runs longer, one-off trips on the same train, such as a six-day journey, mostly around Malaysia, called "Fables of the Peninsula." Check Belmond.com for schedules and prices.

You can also do a much less luxurious version of this journey on Bangkok and Malaysian state railways. Overnight trains from Bangkok to Butterworth leave every day at 2:45 p.m., arriving at 1 p.m. the next day. Butterworth-to-Kuala Lumpur trains depart several times a day, and trains from Kuala Lumpur to Johor Bahru, near the Singapore border (there's a shuttle bus to Woodlands Station), run three or four times a day. Fees start at $145 for tickets, without meals, and include a deluxe sleeper in Malaysia and a second-class sleeper in Thailand. Visit the The Man in Seat 61 website ( seat61.com) for up-to-date schedules and fares.

The writer was a guest of Belmond's Eastern and Oriental Express. The company did not review or approve the story.