To help everyone experience different textures of Singapore, I tried documenting the city’s fleeting moments through multiple mediums this time. The square-format color photos were shot with the vivo X100 Ultra; the rectangular color photos were captured on Kodak Ektar100 film; and the rectangular black-and-white photos were taken on Kodak 400TX. I hope you enjoy them.

From 2023 to 2025, I visited Singapore several times, each stay lasting around four days. It wasn’t rushed, yet my schedule was always filled with work, leaving very little room for free exploration.

And so, Singapore developed a kind of “familiar unfamiliarity” for me—you know its outline, but haven’t quite touched its texture. Before writing this city-wandering guide, I hesitated: after searching through our site’s archive, I realized several outstanding Singapore pieces already existed. Was there still a need for me to “add one more”?

But then I thought: perhaps my perspective is different from others’, and that difference could offer a more spontaneous and unstructured route. So the following guide emphasizes the idea of wandering: go wherever your steps take you, let your thoughts drift, and discover the stories behind what you see. It’s not a tightly curated checklist, but more like offering you a key—encouraging you to enrich your own journey through chance encounters with landscapes and people, and to explore the unknown, delightful world out there. And if it truly works that way, then it will have its own special meaning.

Before We Begin

I have a deep passion for architectural photography, and I especially enjoy understanding buildings by starting from their facades—exploring the roles they play in a community, the intentions of their builders and policymakers, and the relationship between the architecture and its residents. To me, this process is full of joy and discovery. Therefore, I will be sharing a route that lets you explore Singapore’s history through the evolution of its architectural styles.

A Little Disclaimer
This isn’t a traditional travel guide, but I still hope it offers useful references for anyone planning a trip:

• Visa & Payment: Since Singapore implemented visa-free entry last year, traveling there has become much easier. Mobile payment options like Alipay and WeChat Pay are now widely accepted—even in hawker centres—making it far more convenient to enjoy local food.
• Cost of Living: Do keep in mind that Singapore is fundamentally a high-cost city-state. With the recent increase in GST, prices have continued to climb over the past year.
• Weather: Located in the tropics, Singapore is hot and humid from June to August, and rainy, mild, and moist from November to March. This makes April–May and September–November particularly pleasant for visiting.

If I were to summarize it in one sentence—“Is Singapore worth visiting? Is it fun?”—my answer would be: yes, it’s worth going, and yes, it’s fun, but it’s best to manage your expectations. I recommend treating Singapore not as a standalone destination, but as one stop in a broader Southeast Asia journey. See it as part of the larger Nanyang cultural region—together with Malaysia, Indonesia, or even Vietnam—and let the tropical wind guide you through the region’s vibrant, thriving cultures. You might be pleasantly surprised.

Travel Gear
Due to work needs, I had to bring a laptop, three days’ worth of clothes, a pair of slippers, a digital organizer full of power banks and cables, a camera, and essentials like my passport and wallet.

It’s an awkward amount to carry: an 18-inch carry-on suitcase leaves too much empty space, making items shift around; a regular backpack can’t fit everything; and I’ve never liked the clumsy combination of “a backpack plus a camera bag.” After much consideration, I went with the Tomtoc T66 28L backpack.

It has two configurations, perfectly matching my needs. For daily commuting, I tighten the side compression straps to keep it compact and sleek—appropriate for meetings and less likely to bump into people on busy trains. When it’s time to wander, I loosen the straps and lower the internal panel—it easily fits a 15 cm–wide camera insert. With it, I roamed the streets and alleys of Singapore, stopping often to shoot.

In short, it precisely addresses the core pain points of any office worker who loves photography: – backpacks with impractical capacity, – camera bags that are too specialized, – suitcases too clunky for daily transit. This single backpack solves all three.

Of course, it’s not flawless. I noticed that the side compression straps may loosen gradually when walking; a one-way gravity-release limiter would be ideal. And when the backpack is packed and carried only by the top handle, the top fabric feels overly taut from the concentrated stress—I worry about its long-term durability. Distributing the force more evenly across the upper sides might be a better design.

Still, these details haven’t affected my use so far. As someone who has used Tomtoc products since 2021, I genuinely hope this brand continues to get better and better.

An Ocean of Green Life

When you land at Changi Airport and head toward the city, you’ll feel as though you’ve entered a vast garden. Towering trees line the center of the roads, and unlike the trees commonly seen in China, the abundant Southeast Asian sunlight and rainfall seem to infuse them with boundless energy. Their branches stretch vigorously toward the sky, twisting and entwining, eventually forming massive green canopies—like the sprawling green capillaries of this young “Pearl of the South Seas,” leaving behind one of its most vivid urban signatures.

During my ride into the city center, I chatted with a talkative taxi driver. He told me that Lee Kuan Yew had been unwavering about city planning, insisting that “if there is no building by the roadside, there must be plants.” Since the 1960s, Singapore has implemented large-scale afforestation and park-building initiatives, later even legislating mandatory urban greening standards. What began as trees and parks lining the roads evolved by the 1990s into the integration of green spaces into neighborhoods and everyday life. This seemingly simple rule originated from the nation’s early, profound understanding of extreme land scarcity—and its determination to build an eco-friendly city. We’ll see more evidence of this belief throughout the journey.

Chinatown (Niu Che Shui)

Starting your exploration in the Tanjong Pagar area is a wonderful choice. Historically, the district was home to rickshaw pullers, attracting Chinese and Indian dockworkers and gradually forming a working-class community. By the mid-1980s, Tanjong Pagar became the first district designated for conservation under Singapore’s urban protection plan.

We began on Amoy Street. The road is lined with Hakka-style red-roofed buildings. Viewed from above, the layered rooftops resemble a sea of time, while the intricate ridge decorations and carved eaves glisten under the sunlight, piecing together the warm, collective vision of “home” held by Chinese laborers who once journeyed south a century ago. Not far away stands the 1970s-built People’s Park Complex, rising like an unshakable red lighthouse.

Many of the buildings here, constructed from the late 19th to early 20th century, once served as clan associations, ancestral halls, and shophouses. After careful restoration, their facades are beautifully preserved—some converted into hotels, others into restaurants, bars, or museums. You can explore freely, following your interests wherever they lead.

Continuing onward brings you deeper into the Chinatown district—a microcosm of Singapore’s defining characteristic: multicultural coexistence. Despite being called “Chinatown,” here you’ll find Hindu temples and mosques standing side by side with Chinese schools and clan associations. Many revitalized shophouse arcades also appear to grow without strict functional constraints—cafés, Northeastern Chinese restaurants, Korean barbecue joints, and various small shops cluster together, serving the needs of nearby residents with a natural, almost “wild” vitality.

If you choose to visit at night, you’ll have a completely different experience. The Chinatown Complex has long shed its daytime bustle, yet the square in front remains brightly lit. In the pavilion, uncles gather in three tight circles, chatting in Hokkien as all eyes fix on the two players battling at the center of each ring. A few steps away is Club Street—its English name already tells you what it was made for. The area comes alive at night: soft music drifts through the air, and the laughter and clinking glasses from stylish bars spill out onto the street.

CBD

Just one street away from the low-rise Nanyang shophouses—Telok Ayer Street, Stanley Street, South Bridge Road—towering office buildings suddenly take over your field of vision. You crane your neck upward, past layer upon layer of shimmering glass façades, hoping to catch sight of the rooftop where the building seems to meet the sky. You’ll notice that the skyscrapers here look distinctly different from those in major Chinese cities.

Singapore has expanded the traditional boundaries of the “CBD” by significantly reducing purely commercial zones and introducing extensive mixed-use areas that blend offices, residences, and amenities. Over the next five years, the development of Tanjong Pagar will focus on livability—adding more green spaces, covered walkways, and pedestrian-friendly paths, while improving accessibility to create a sustainable, comfortable urban environment.

In terms of aesthetics, many office buildings boldly embrace irregular lines. Their clean glass façades emit a cool glow, while vast open atriums become communal spaces where people and greenery coexist harmoniously. These buildings don’t mind letting plants climb, drape, or even envelop entire surfaces.

Singaporeans, who never waste a single square meter, are surprisingly generous when it comes to plants. The “vertical garden” at Parkroyal Collection Pickering softens the cold rigidity of urban architecture with warm, fluid lines, transforming the hotel into a green gem in the heart of the city. Meanwhile, Oasia Hotel Downtown dedicates nearly 40% of its volume to vertically integrated public greenery. Its striking red façade symbolizes tropical warmth, while 21 species of lush climbing plants weave an elevated green sanctuary that shields guests from urban noise and stress. This extreme pursuit of efficiency and ecology is deeply rooted in Singapore’s unique land policies—and nowhere is it more evident than here.

Land Policy

As you wander through Singapore, you may begin to wonder: the streets are filled with beautifully preserved century-old shophouses and sleek, modern sustainable buildings—but where did the industrial-era structures from the 1960s to 1990s go?

To understand Singapore’s interwoven yet somewhat “gap-filled” urban landscape, we must return to the origins of its land policy. When Lee Kuan Yew took office in the mid-20th century, newly independent Singapore was far from the prosperous city we see today—it was a small, troubled place filled with overcrowded slums and social unrest. On this tiny island nation, land was the most precious strategic resource. In response, the government intervened decisively in urban planning, reshaping the nation’s spatial logic through an extensive system of land-use laws.

Today, roughly 90% of Singapore’s land is essentially owned by the state. This highly centralized ownership model grants the government an extraordinary level of control—functioning almost like the island’s most efficient urban designer. This explains Singapore’s distinctive “time-jumping” architectural feel: on one side, you have the CBD’s glass megastructures forming a world-class skyline; on the other, meticulously restored, low-rise Nanyang shophouses preserving the charm of the past. But lying between these two extremes—the era representing the utilitarian, cost-efficient industrial construction from the 1960s to 1980s—many buildings from that period have simply “vanished” from entire districts. Those grey-walled factory blocks and repetitive housing slabs faded as the government rolled out regular mandatory upgrading and redevelopment programs, quietly erasing the rough textures of that era.

Thus, walking through Singapore often feels like strolling through a perfectly run “SimCity”: at the macro level, history, aesthetics, and function are all neatly planned. But when you look closer, you notice the everyday imprints of life—aromas of homemade food wafting through corridors, potted plants on balconies, clothing drying in the breeze, bicycles parked at stairways. These small, spontaneous details breathe warmth and soul into the city.

As early as 1959, the People’s Action Party made “providing affordable housing for the poor” a core campaign promise. After taking office, the new government moved swiftly, passing the Housing and Development Act to tackle the housing crisis. On May 25, 1961, a devastating fire swept through the Bukit Ho Swee squatter settlement, burning down approximately 16,000 homes in a single night. This tragedy became a brutal catalyst, dramatically accelerating the construction of public housing—much like how Hong Kong’s 1953 Shek Kip Mei fire spurred its public housing system a decade earlier. After decades of development, HDB housing has become home to over 80% of Singaporean citizens.

The design of HDB estates carries the spirit of a “vertical village.” Each block features a large “void deck”—an open communal living room filled with stone tables and benches where residents gather to chat and socialize. These spaces, together with surrounding community gardens and sports facilities, foster frequent neighborly interactions and redefine community cohesion in high-density urban living. The Singapore government also enforces a racial integration policy within HDB estates, setting quota limits for each ethnic group. This ensures that people of different backgrounds live side by side, naturally interacting through daily routines and shared facilities. Starting at the neighborhood level, these measures serve as the foundation for racial harmony—and, to some extent, support social mobility as well.

The Pinnacle@Duxton and Everton Park

You’ll pass through the carefully polished pedestrian streets of Chinatown—pleasant and tidy, though sometimes lacking a bit of raw, everyday life. But as you continue westward and turn onto Everton Road, the bright colors remain, yet the atmosphere shifts. Here, life is closer to the ground. At the end of the row of vibrant traditional shophouses stands the massive HDB development The Pinnacle@Duxton—a grey modern giant rising into the sky, yet thanks to clever design and proportions, it doesn’t feel oppressive at all.

The Pinnacle@Duxton, composed of seven towers, is the world’s tallest public housing project. Completed in 2009, it features sky gardens on the 26th and 50th floors—the longest sky gardens on Earth, each stretching 500 meters. Its most striking feature is how its scale, design, and façade rival those of private condominiums, while it remains, in essence, genuine public housing. The sky deck on the 50th floor is open to the public—just 6 SGD grants you a panoramic view of Singapore’s urban magnificence.

“They built something this monumental… for public housing?” This is the first thought many have when they see the structure. Indeed, this massive concrete landmark—visible from multiple angles across the city center—stands as a symbolic statement of Singapore’s public-housing vision, a tangible testament to the government’s determination to ensure “a home for every citizen.”

If you wish to experience the atmosphere of Singapore’s earlier HDB estates, the neighboring Everton Park is an essential stop. Built during the Malaysia–Singapore merger era (1960s) and incorporated into the HDB system after a 1979 renovation, this estate resembles Hong Kong’s public housing: large, geometric blocks defining the skyline, softened by gentle curves. When afternoon sunlight washes over them, the walls seem to glow with the warmth of decades of lived experience.

A long 100-meter corridor links the homes. Balconies overflow with lush plants, vines cascade like green waterfalls, and patterned quilts sway in the sunlight. Bicycles rest casually by staircases. Below, decades-old shops coexist peacefully with trendy Nanyang-style cafés. In the small park, an elderly auntie sits alone in a pavilion soaking in the sun, while a few Indian youths chat leisurely nearby. Here, buildings cease to be cold containers; they become warm backdrops to everyday life. For over sixty years, HDB public housing has been deeply woven into Singapore’s social fabric.

Once you understand this history of rebuilding from ashes, the endless rows of HDB blocks no longer look like monotonous repetition. Instead, they represent the enormous effort a nation has made to provide stability for its people. Though Singapore occupies a golden position along the Strait of Malacca, its path forward has never been effortless. To ensure its citizens can live securely and with dignity, both the state and the government have invested tremendous and sustained effort.

Tiong Bahru

Continuing westward, you’ll arrive at Tiong Bahru.

“Tiong” comes from the Hokkien word thiong (塚), meaning “cemetery,” later replaced with the character “中” for convenience; “Bahru” means “new” in Malay. In the 19th century, this area served as the burial grounds for the Hokkien community. In 1925, due to poor sanitation, the Singapore government began clearing the area—relocating squatters and flattening the cemetery.

In the 1930s, the Singapore Improvement Trust—the predecessor of today’s HDB—began planning and building one of Singapore’s earliest public housing estates. This laid the foundation for the unique blend of history and aesthetic charm that Tiong Bahru is known for today.

During the 1920s and 1930s, rapid developments in aviation and technology inspired architects to incorporate ideas from fluid dynamics and biomimicry into building design. As a British colony at the time, Singapore naturally absorbed these influences. Thus, Tiong Bahru did not follow the later, efficiency-driven logic of public housing but instead adopted many stylistic and decorative innovations of the era. Architecturally, it sits at the intersection of Art Deco and Streamline Moderne, styles that can also be found in Shanghai.

Walking through the neighborhood, you’ll notice the so-called “airplane buildings” and “horseshoe blocks.” These low-rise structures—generally six storeys or fewer—feature sweeping horizontal lines, rounded corners, external spiral staircases, and round porthole windows in the stairwells. They stand in stark contrast to the modular, repetitive façades of typical high-rise public housing. The curving forms lend the buildings a sense of vitality and rugged elegance.

Deeper into the estate, you’ll find iron-grille window panels, old sliding doors, and balconies each with their own character. Strolling through quiet lanes, the low-rise blocks nestle beneath lush foliage, their faded verandas facing towering HDB blocks across narrow streets. At ground level, residents cultivate vibrant flowers and greenery, imbuing the tranquility with everyday warmth.

Thanks to ongoing restoration and revitalization, Tiong Bahru preserves not only the traces of cultural figures like Yu Dafu and Xu Beihong, but also its lively, grounded neighborhood spirit. The neighborhood temple, old coffee shops, and hawker center sit alongside the cafés, bookstores, and boutique shops that have emerged in recent years—not jarring, but adding a touch of lightness. Tiong Bahru is elegant yet playful, old yet young—continually performing a timeless dance of ordinary, beautiful urban life.

New Bahru

After taking in the unique public housing charm of Tiong Bahru and grabbing a meal to recharge, you can head north, cross the Singapore River, and arrive at New Bahru Creative Park.

New Bahru was originally the campus of Nan Chiau High School (formerly “Nan Chiau Girls’ School”), a place filled with the memories of generations of students. Today, the former school building has been transformed into a lively hub for art and commerce. Situated partway up a gentle hill, you can reach it with a short walk past low-rise landed homes shaded by dense greenery. Then, the iconic red façade and stylized “New Bahru” lettering reveal themselves.

The campus-like layout remains: the area is divided into two main blocks, with a courtyard in between that features grassy lawns and slides for children—continuing the community vitality of its past. Most shops are housed in the main building (Big Block), where the first floor is lined with cafés and eateries, while the second and third floors host a variety of design-focused boutiques waiting to be explored.

Here you can find curated baby products, the ever-popular Jellycat plush toys, leather-crafting workshops, and independent fashion boutiques featuring niche aesthetics. Interestingly, I stumbled upon a plant shop on the second floor—lush with greenery from floor to ceiling. Beyond selling plants, it offers workshops and cultivation classes, inviting you to create your own indoor oasis. The store embraces a Japanese wabi-sabi sensibility—simple, humble, quietly serene. Of course, beauty comes at a price, but the chance to immerse yourself in such a rare, atmospheric shop is itself a memory worth keeping.

Other Options

After you finish exploring the shops in New Bahru, you may walk east toward Fort Canning Park, take a photo at the famous “tree tunnel,” or continue north to visit the National Museum. You could stop by Little India for snacks; or walk south to Marina Bay, snap a perspective-trick photo with the Merlion, and admire Marina Bay Sands, the ArtScience Museum, and Gardens by the Bay—icons of Singapore’s cosmopolitan image.

On day two, if you have more time, consider exploring Singapore’s East Coast. Visit Soekarno Cat Hotel on Joo Chiat Road to exchange a few meows with the feline manager; visit the Peranakan Museum to understand how Chinese migrants put down roots over the past century; and taste unique Peranakan cuisine. Or stroll down Koon Seng Road to admire the colorful shophouses.

You might also pick up a drink and some snacks at a local mart, walk a few steps to East Coast Park, and rest on a bench to simply… think of nothing. Let your gaze drift across the open sea—you’ll notice cargo ships scattered along the horizon. Roughly a quarter of the world’s goods pass through the Strait of Malacca each day. In that moment, the reality of Singapore’s strategic position at a global crossroads hits you more tangibly than any textbook could explain.

Conclusion

The end of every wander is the beginning of a new understanding of a city. For me, Singapore is no longer a one-dimensional “Garden City.” Its meticulous order and untamed vitality, its grand narratives and daily warmth, are woven into a complex and fascinating web.

I still remember, as I was heading to the airport, a chicken—yes, a chicken—strutting confidently along the pedestrian path ahead of me. Its white feathers impossibly pristine, its comb bright red and upright. Behind it walked an elegantly dressed woman. In a pickup truck stopped nearby, six Indian workers perched on the side benches watched the chicken with the same curiosity as I did. Their skin was deep brown, their hair curled, their bright eyes slightly tired—they were on their way to a construction site, but in that fleeting moment, we were all simply observers of a charming, unexpected passerby.

Singapore is a pearl of the tropics: well-dressed office workers, gleaming shophouses, towering skyscrapers—and behind them, countless people quietly supporting the machinery of prosperity and spectacle, just as in every city and every civilization. At that moment, I fully embraced my “familiar unfamiliarity” with Singapore. The interplay of old and new, light and shadow, and the constant collision and fusion of cultures—these are what give Singapore its truest, most captivating soul.