The Manila Galleon is such a historical aberration, and yet is still there in the surnames, the streets, the collective memory. As I strolled down some remarkably quiet backstreets, I felt I was on a heritage island stranded in a city bent on new-build and road-build. But the blazing sunshine and humidity soon began to get to me, as I walked from bastion to bastion, tracing the old walls around the city, and something other than the heat pressed in on me - alienation, perhaps, and a sense of displacement.

Enigmas in travel are few and far between, especially when it comes to big cities. Most are overexposed in the media (New York, London, Paris), wrapped up in cliches (Edinburgh, Los Angeles, Vienna) or rammed with tourists (Bangkok, Barcelona, all of the aforementioned).

But Manila is associated with a complex set of unknowns. You arrive asking: 'Will it be safe?' The Hong Kong government has still not lowered its black travel alert on the Philippines that has been in place since the August 2010 tourist bus hijacking by a disgruntled former policeman in which eight Hongkongers died.

Walking beneath the overhangs of Leandro Locsin's Philippine International Convention Centre, I was able to retreat from the heaving city and enter into a conversation with the sublimely abstract. The cool forms of the building - Locsin was a master-pourer of concrete and a poet of tropical brutalism - made me think of Brasilia, car parks and military monuments. Nearby were the Manila Film Centre and the Cultural Centre of the Philippines. For a couple of hours I walked around, stroking the cool surfaces, lingering in the shadows and wondering, again, this architecture wasn't famous and why Locsin wasn't known as the East Asian Oscar Niemeyer.

In a way, the modernist architecture is an antidote to the headiness of Manila. It is, in many ways, a chaotic city, typically Asian yet with a veneration for the automobile that's wholly American. (You can't cross the road in Makati without using a labyrinth of tunnels and raised walkways.) If you take Manila's famous jeepneys - the chrome buses originally made out of American military jeeps left after the second world war - as a central metaphor, this is a city of visual bling, formal filigree, general busyness. Locsin's plinth-like buildings are, by contrast, steady, calm, plain spaces, easy on the eye and soothing to the soul. Modernism is old now, and it has a nostalgic 'future in the past' quality, like a Jetsons cartoon.

According to revered Manila guide Carlos Celdran - whom I met for a coffee the following day at Greenbelt, an exclusive mall in Makati - the architecture is just one element in a national identity crisis. 'In the 1970s and 1980s, our first lady, Imelda Marcos commissioned several large-scale modernist edifices to be constructed all around the Philippine archipelago,' he said. 'The modernist structures can be seen as emblematic of her husband's 'progressive' vision for a New Philippine Society, or Kilusang Bagong Lipunan, as we say.'

But the buildings, he argued, remain fundamentally out of place. 'The fact that the Philippines has pretty much gone directly from an agricultural age into a cyber-age places these structures in some odd architectural limbo.'

After a trip to the Church of St Andrew and a tour of my own hotel, I was sated on Modernism.

Before I left, I decided to head over to the Manila Hotel. It was here, between 1935 and 1941, that General Douglas MacArthur set up his military HQ and, out back, I spied the docking area where seaplanes used to arrive, carrying Glenn Miller and his big band, starlets, Hollywood actors and writers.

It was dusk when I arrived (another long taxi ride), and a storm was rolling in and forks of silver lightning were dancing out on the sea. I ordered a Martini and watched the sun set, wondering why the sun always seemed to be setting on Manila. I love out-of-the-way places, cities that never get in those top 100 lists. Just what I needed before the long flight home.

Walk this way with Carlos Celdran

Van Gogh is Bipolar 154 Maginhawa Street, Sikatuna Village, Diliman, Quezon City

'At this cool Quezon City hangout, owner and chef Jetro Rafael tailors menus to suit his clients' mental states and personalities, and believes in the psychological power of food: everyone knows chocolate can be a pick-me-up, but did you know turkey can calm the mind? The best part thing about dinner here: prices are only 'recommended'. After dinner, check out the surrounding neighbourhood of Maginhawa Street, Manila's newest hipster wasteland.'

Philippine International Convention Centre CCP Complex, Roxas Boulevard

'Leandro Locsin's design is bold, brutalist, and was the first of its kind in Asia. It elevated a banal concept such as a convention centre into a massive gesamtkunstwerk (total work of art), where even the doorknobs of the bathrooms and light fixtures have the touch of the architect's aesthetic. Its use of Modernist elements makes the PICC both Filipino and international, ancient and modern, organic and industrialised. It's a high moment in 1970s architecture, and Lord knows there aren't many of those.'

San Sebastian Church Plaza del Carmen, Quiapo

'Tucked away in the old Quiapo neighbourhood near the presidential palace of Malacanang, San Sebastian is a neo-Gothic church made completely out of steel imported from Belgium in the late 19th century. It was said to be the Philippines' answer to Paris' newly inaugurated Eiffel Tower. I know, it sounds crazy. But you should see it. It is.'

Marikina Shoe Museum JP Rizal Street, Barangay San Roque, Marikina

'Ever wonder what happened to the infamous shoe collection of the Philippines' flamboyant former first lady? Well, look no further. It resides in a little suburb on the edge of Metro Manila called Marikina. Renowned for its shoe-making industry, Marikina opened a museum dedicated to shoe history with the collection of Imelda's size 81/2s as the main attraction, complete with photographs of the one-time beauty queen at the event where she wore each pair.'

Markets Salcedo Market: Tordesillas Street in Salcedo Village, Makati Legaspi Market: Herrera and Salcedo Street Parking lot, Legaspi Village, Makati

'The best thing to ever happen to bland, corporate Makati, the Salcedo Saturday and Legazpi Sunday Markets are held in the main parks on each side of the central business district. They are a great place to meet locals and to check out the latest in Philippine artisanal cuisine, produce, handicrafts and organic products. Go early, as it tends to get hot by the middle of the day. And take cash. Artisan types apparently don't accept credit cards for now.'

Where to stay

For more from Carlos Celdran: celdrantours.blogspot.com