A Luxury Train Ride From Singapore to Malaysia Redefines “Heritage”

A little over two centuries ago, British capitalist Stamford Raffles planted a trading post at Malaysia’s dangling tip and named it after Singapura, ancient Sanskrit for “lion city.” Laborers from China, India, and greater Malaysia heaved mountains of earth into the muddy estuary of the Singapore River to create new land for developers to lay the city-state’s foundations. The investment paid off, at least for the capitalists. Singapore, today about the size of New York City, is a global commercial center—a safe, efficient, English-speaking, litter-free outpost for Western companies in search of Asian markets, and vice versa. 

Sure, jaded leisure travelers might find it a tad dull compared with regal Bangkok or clamorous Hong Kong, but the business of Singapore is business, and always has been. The national mindset is pragmatic, unsentimental, and profit-oriented. In a place where space is forever at a premium, the churn of property development—build, tear down, rebuild higher, repeat—is what plowing the land is to a great agricultural nation: a cyclical harvest, even a patriotic destiny. Real estate speculation and its twin, banking, have offered the generations the surest way to sow ambition and reap prosperity, making faith in future growth almost a geographic feature. From the top of One Raffles Place, once the tallest skyscraper in all of Asia, the economic outlook is almost invariably sunny.

“Singapore is future-positive,” is how the Australian architect Richard Hassell put it to me when we met at 21 Carpenter, a hotel designed by his firm, WOHA Architects. Our conversation came midway through my stay in the city, which was to be the point of departure for a train journey through Malaysia on Belmond’s Eastern & Oriental Express. Before setting off, I wanted to explore the city itself. Above all, I was curious about what a relentless focus on progress might mean for visitors drawn to history and culture—visitors, like me, who typically avoid bright, shiny, ultramodern cities. 

On my wanderings so far I’d seen low-rise neighborhoods of mom-and-pop shops, Anglican churchyards, and manicured parks, all dwarfed by glass-and-steel skyscrapers. I’d seen architectural doodads of delirious invention and vine-hung eco-utopian prototypes for the climate-change future. Each phase of the past had its own vision of tomorrow. “Singapore is very pro-change,” Hassell agreed, explaining that when change equals investment and investment equals profit, people can’t wait to move on to the next thing.

The newest next thing is symbolized by 21 Carpenter, where Hassell fitted 48 rooms into a tower wrapped up in a perforated, heat-deflecting aluminum sun canopy. The novelty is at ground level, where the tower’s base rises not from land scraped clean of its past but from a restored 1936 remittance house—an early financial institution used by Chinese laborers to send their earnings home. 

Hassell preserved the original stucco façade and tiled roof. He also read workers’ letters home to their families and gathered poignant phrases—bits of found poetry—to inscribe on the sun canopy. The new building bears witness to the old city, preserving the stories of forgotten immigrant workers, the people who built Singapore. After its opening last year, the Singapore Institute of Architects named it the 2024 design of the year.

Heritage was the buzzword of my trip, shorthand for the pendulum swing away from a raze-and-replace mentality toward one of restore and refurbish. The movement began in the 1980s with adaptive-reuse projects in Chinatown’s historic shop-houses, then grew to include major sites like New Bahru, a former high school converted into an eat-shop-stay campus. 

The meaning of heritage has also continued to expand. Raffles Singapore, once a symbol of British colonial snobbery, reopened in 2019 after an estimated $200 million restoration with new décor and a new self-image. “Heritage is also stories,” in-house historian Nazir Yusof told me. Raffles trained a next-gen team to diversify its storytelling, bringing overlooked voices into its account of the colonial era, which in this part of the world has too often represented only the British experience—the colonialists’ point of view. 

In 2023, Raffles awarded its writing residency to a Singaporean for the first time. Poet Madeleine Lee’s resulting collection, How to Build a Lux Hotel, is a native daughter’s intimate and funny view of the grande dame—a peek up her skirt, as it were. The next residency went to Taiwan-born, Paris-trained, Singapore-based chef André Chiang, who produced a book brimming with stories and recipes; its recent publication precedes the opening of a new Chiang restaurant at Raffles later this year.

Elsewhere in town, savvy entrepreneurs are feeding the heritage trend by making history from scratch. Witness the neo–Art Deco bar Atlas, a fixture on the World’s 50 Best list, or the brand-new old-timey eating spot with the on-the-nose name of Great Nanyang Heritage Café.

Meanwhile, the E&O Express is a celebration of the region’s artistic legacy and natural biodiversity. I booked a three-night journey through the Malay Peninsula, departing from Singapore. The trip offered stops to hike a rainforest filled with gibbons and to tour George Town, the pre-Singapore British entrepôt where an elite strata of Chinese-Malay families known as Peranakans built elaborate mansions. 

When I got back to Singapore, I learned that August 2025 would mark 60 years since the city-state declared its independence and placed leadership of a melting-pot people in the hands of Lee Kuan Yew, its first prime minister. From 1959 to 1990, LKY, as he’s known, engineered the country’s rise from postcolonial poverty to first-world prosperity. Today he is regarded as a national hero, a founding father as visionary as FDR and shrewd as LBJ. What I observed on the eve of the historic milestone was a country actively reassessing its remarkable rise, not only focused on a headlong rush into the future but also discovering the power of its own diverse history. 

Boarding the stately hunter-green-and-Devonshire-cream Eastern & Oriental Express at Singapore’s Woodlands train station, the third thing I fixated on—after the high crew-to-guest ratio and the acres of interior marquetry—was the boarding pass. The ultra-thick paper was fit for a royal invitation, and the Art Deco design featured an elongated tiger, as if frozen midway between the past and the future. “The lure of Malaysia in motion,” read the motto. I laid the invitation on a tea table set with porcelain and silver, ran my hand over an emerald velvet armchair, and petted a dragon-embroidered pillow. Minor details, perhaps, given the cinematic three-night trip ahead, but the fine paper and fabrics caught the spirit of the refurbished E&O: analog, fancy, and fun. 

As the train sped into the gathering dusk and a piano-sax duo played Jazz Age ditties, 40-odd passengers, some dressed in black tie and formal dresses, mingled over cocktails like guests at a country-house weekend. One fellow produced a deck of cards from his dinner jacket—the onboard magician. He asked the woman nearest him to pick a card, look, and return it, face down, to the deck. Then the magician pulled a fresh lime from his pocket and sliced it open to reveal a folded card. She unfolded it: the queen of clubs, the same card she had picked from the deck. 

The next morning, the train came to a halt in the middle of wild Malaysia, right alongside Taman Negara National Park. The trainload of passengers, now kitted out for a jungle excursion, stepped out into tropical heat and loaded into a caravan of open-air jeeps to explore the park. Our introduction to Malaysia would begin with the backstory—way, way back. 

The rainforest that soon enveloped us has been evolving for some 130 million years. At our first stop in the park, our guide showed us the jungle canopy from above, from a platform with spectacular views of primordial forests and distant mountain peaks. Farther in, we followed a hiking trail beneath the orchid-hung canopy. Keening gibbons in the valley to our left were answered by a troop to our right. The region’s few remaining elephants and tigers, we were told, moved unseen through the park’s hidden reaches. We returned for lunch on the rails and watched endless miles of palm-oil plantations roll past the windows, former wilderness traded for profit. 

Of course, it was the fat of this land—wealth from nutmeg, then rubber and palm oil—that drew the British to Malaysia. More than 30 years before Singapore’s founding, the Union Jack flew over the state of Penang, across a narrow strait from where the E&O eased to a stop at Butterworth station. 

The British East India Company’s urban plan for George Town, the capital of the state of Penang, remains intact, and I toured the gridded streets from a recumbent position, laid out like a bunch of bananas on the basket-chair of a bicycle rickshaw. Its driver, Mr. Lim, pedaled me past the blindingly white Eastern & Oriental Hotel—opened as the Eastern in 1884 by the Persian-Armenian Sarkies brothers and unaffiliated with Belmond’s E&O Express—and delivered me to two colorful heritage houses. 

The first was an indigo-blue mansion built in the late 19th century by merchant-prince Cheong Fatt Tze and styled as a mah-jongg parlor in the movie Crazy Rich Asians. Its complement, formerly the home of tycoon and philanthropist Chung Keng Quee and now the Pinang Peranakan Mansion, was painted the precise food-coloring green of Malaysian pandan cake. The grand Peranakan families represented a rapid social ascent: from immigrant labor to merchant class to tycoons in a century. They spoke the Queen’s English, venerated Buddhist deities, served Malay curries on porcelain, and filled their houses with a mix of Chinese antiques, French enamel, and furniture in the Georgian style—here richly decorated with dragons and phoenixes. “We are a fusion country,” Mr. Lim explained.

The E&O was Singapore-bound again when train manager Wolfgang Eipeldauer dropped by my cabin to connect a few dots. Before the recent revamp, he told me, the train harked back to “a British hill-house veranda in the tropics.” For the current incarnation, he said, “we purposefully tried to pay attention to the regional and the local.” The idea was to correct the tendency, common in luxury hospitality, to see colonial opulence only through British eyes. The new E&O, like the old Peranakan elite, spans two worlds.

On his way out, Eipeldauer suggested I find time for a coffee with Kishen Muruganandan, the bar manager. I made an appointment and met him in the plush caboose. Muruganandan was Malaysian, he told me while brewing a cup, as was most of the young crew. The coffee beans were Malaysian, grown by a neighbor in his home village. The stylish crew uniforms, he replied when I asked about them, were Malaysian, created by a designer in Kuala Lumpur. I caught Eipeldauer’s drift: to learn about heritage, talk to someone for whom it is a birthright. Malaysia in motion, indeed.

Singapore refutes the old adage about land—here they are still making it. It was the day after the E&O rolled back into Woodlands station, and I was luxuriously billeted at Raffles Singapore. After breakfast in the Tiffin Room, I joined a hotel tour led by Yusof, the in-house historian. “This was a beach house,” he told us, launching into the story of the Sarkies brothers. 

Flush with cash from the success of their Eastern Hotel in George Town, they opened Raffles in 1887 with 10 rooms across from the beach, perhaps taking Sir Stamford’s surname to suggest a starchier British pedigree than they themselves possessed. Today the waterfront is 2½ miles away: Singapore has added approximately 25 percent more land since Independence. 

Raffles has grown at a considerably higher rate. Its 10-acre hospitality-retail complex now contains 115 suites, seven restaurants and bars, and a platinum-card-melting shopping arcade. Looky-loo tourists with selfie sticks constantly stream past the white-on-white high-Victorian façade of pediments, pilasters, and cast iron. The building has been an official national monument since 1987, Yusof told me with the indulgence of a father whose child is often complimented by strangers. 

It is, in fact, something more than that. Like the Eiffel Tower and the Empire State Building, Raffles is a symbol of the city, even a flagship for the nation, explained a Singaporean wine importer I met for drinks at the Long Bar, home to the rather-too-sweet Singapore Sling. He likened Raffles to a state weather vane: it always points toward the future. A tropical haven for travelers in the imperial “golden age,” the hotel later hosted LKY’s wedding reception (the city’s first prime minister returned annually for anniversary dinners) and now is a gilt emporium for the global rich. As Raffles goes, so goes the nation, the wine importer said.

I was surprised, then, that the concierge sent me straight away to the Intan, a private museum in a distant residential quarter where the curator-docent-occupant-in-chief was a voluble Peranakan storyteller named Alvin Yapp. He showed me his 1,500-piece collection of decorative arts, then over tea he expounded a theory. Singapore’s cosmopolitan business savvy, Yapp proposed, can be attributed to the cross-cultural fluency of its Peranakan citizenry. About three-quarters of Singapore’s residents claim Chinese descent and, at the same time, English is its mother tongue and business lingua franca. In other words, the city-state’s intellectual framework consists of a language, legal code, parliamentary system, and free-market orthodoxy, all left behind by the British when they vacated their columned administrative buildings. The result has been profound. “We think like Westerners,” Yapp said with an ironic smile.

After tea at the museum, I had drinks with a poet. Madeleine Lee was waiting for me in Raffles’s Writers Bar, dressed in the edgy black avant-garb of a contemporary art dealer. The title of her book, How to Build a Lux Hotel, suggested an instruction manual. The elegant poems inside presented this conclusion: you build it with people. Lee told me she studied the changeable dramatis personae at Raffles during a dozen stays by talking to bartenders and observing maids and gardeners making their rounds and guests drifting through the spangly lobby. Lee said she tried to capture the emotional feel of the place because so much had already been said about “the founders, the architecture, the whole colonial thing.” 

I was curious what a poet, with her sensitivity to language, would make of the word heritage, which by this point in the trip had thoroughly occupied my mind. Lee thought for a moment and described the “family dialect” of blended Malay, English, and Mandarin spoken in many Singaporean homes. “We throw everything in a pot and speak ‘Singlish.’ ”

At a literal crossroads of culture, heritage will have nuances, she continued. There are the sturdy facts of textbook history; then there are family stories and an individual’s own emotional biography—a grandfather’s tale of arriving in Singapore with one small suitcase, for example. Heritage is the past, Lee said, but it must be kept fresh. “If you don’t know where you came from, you can’t appreciate today and the future.”

I started to wonder: how old does something have to be to qualify as heritage? The responses I got from others were inconsistent. Someone said the cutoff was 1900, another said 1965. “It’s heritage if it’s entwined with our city’s past,” replied a Gen Z Singaporean. What about a skyscraper from 2000? “That’s the present,” she said. 

Architect Richard Hassell proposed that heritage is a building old enough to tear down. Twenty-five years after construction, when materials get tatty and tastes change, is the danger time. If the building survives longer, someone will embrace its vintage cool and perhaps a consensus will consolidate around the “authenticity of its times,” winning it government protection. 

Hassell cited a 1982 concrete ziggurat near Orchard Boulevard by American architect John Portman, inventor of the atrium hotel. His innovation swept the world—glass elevators were to hotel architecture what Juice Newton was to Top-10 radio—and then, just as quickly, became unspeakably outdated. Renovated and reopened in 2024 under the name Conrad Singapore Orchard, Portman’s design now defines the cutting edge of heritage.

Heritage doesn’t have to be stuff, however. No less an authority than UNESCO conferred on Singapore’s hawker culture—the tradition of eating at public markets and food halls—the status of “intangible heritage.” (In the name of reportage, I went out for a plate of tangibly satisfying Hainanese chicken rice.) 

The whole picture came together for me at Candlenut, a restaurant in a restored British army barracks across from the Singapore Botanic Gardens. The waiter explained that the dishes by chef Malcolm Lee, who identifies as Peranakan, were inspired by family recipes his mother and grandmother taught him and made using local ingredients because early Peranakan families, formed through a Chinese-Malay union, had to work with what little they had. 

“That’s the story of Peranakan cuisine,” said the waiter. I asked if the style of cooking was popular with Singaporeans. “It is part of their heritage,” he answered. The meal was certainly delicious—the restaurant has been awarded a Michelin star. The experience stayed with me not because of the chef’s technical skills but because the meal told the story of a nation. 

When I touched down at Singapore Changi Airport 10 days earlier, I had wanted to learn what a future-forward society like Singapore does with its own past. Candlenut had the answer, and it goes something like this: the Lion City has taken the measure of its success and, in glancing back over its shoulder, has rediscovered what’s new again. 

A version of this story first appeared in the August 2025 issue of Travel + Leisure under the headline “Time Travel.”