With two guidebooks on Singapore to my name, you could say that I have mastered the Lion City. I have walked the alleyways of Little India, basked in bright lights and lady boy smiles on Orchard Road. I have even ridden the G-Max reverse bungee without vomiting all over the revellers on Clark Quay. Yet despite these – and other, even more illustrious achievements – deep down, I feel like a fraud.

You see, one thing I have not done is this: I have never finished the Joo Chiat Food Walk.

Tony Tan's food walks are a Singapore institution, not in the mainstream Duck & Hippo Tour (www.ducktours.com.sg) sense, but as in "people who want to know the real Singapore need to do Food walk" tour way.

Before I go any further, two points need to be made in the name of full editorial disclosure.

One: Tony Tan is a friend of mine. However, I am famously most critical of those closest to me. Thus, readers can rest assured that I refer to Mr Tan as "a walking encyclopedia of Singapore" with all journalistic integrity intact.

Two: I am convinced that Tony is trying to murder me through overfeeding.  If  my bloated body should turn up in the Singapore River stuffed colon-to-oesophagus with butter nan, chicken rice and Char Kway Teow, cheeks filled with Rojak and both hands gripping chili-pepper crab claws, my posthumous wish is for this essay be used as evidence for the prosecution.

On to the story:

Determined to finally finish the food walk - I had attempted it twice already, only to bow out somewhere between the Buah Keluak and chilli-pepper crab - I begin the day with a lighter than usual breakfast. Some fruit, yogurt and two cups of Singapore's blood-thick Kopitiam, the notoriously sweet coffee that is brewed in a sweat sock.  Naturally I am peckish when lunchtime rolls around, but my journalist's sense of discipline prevails. I am able to sate myself with a very small order of Hainanese chicken rice, in portions that are by Singapore standards barely an aperitif.

To say that I am hungry when dinner rolls around would be an understatement. I am hungry all right - hungry enough to finish the job.

Tony begins the tour, as always, with a bit of knowledge to whet the collective appetites, a brief introduction conducted with visual aids laid out on the Betel Box pool table. Soon after, we are heading up Joo Chiat Road.  Our first stop: a small stall selling Malaysian curry puffs, to be consumed on the roof of a nearby government housing block looking out over the neighbourhood and Indonesia.  I pace myself, eating only two beef puffs and one vegetarian as Tony explains the importance of Singapore's government housing scheme. (Long story short: more than 85% of Singapore lives in government built housing, and you will find a microcosm of the Lion City on every floor).

The next stop is Jenny's, a simple shop with a nearly grotesque abundance of description-defying tropical fruits hanging from every beam and sitting on every raised surface.  The shop is a staple of Tony's tour, and Jenny has already laid out for the group fruits rarely seen outside of Southeast Asia - mangosteen, water apples, dragon-eye fruit and more.

Some of the fruits are a hit with the group. Others, less so. One backpacker from Montréal unceremoniously dumps a chunk of jackfruit into a trash bin. While the rest of the group gorges, I pace myself, knowing what is next on the menu. Oddly enough, the jackfruit-canning Canadian backpacker eats several chunks of the durian, the king of all fruit, whose rank odour has led to its banning on all public transportation and most finer hotels. "It is like either really bad cheese or really good cheese", he says. "I can't quite decide."

The tour pauses momentarily before a mosque on Joo Chiat Road. Ramadan fast has just been broken, and the pious sit inside feasting while the less-so stand outside smoking cigarettes. As we munch the last of the curry puffs, Tony lays down Singapore's golden rule on religious tolerance. In a nutshell: worship as you please, proselytising is forbidden and Jehovah's Witnesses & Scientologists need not apply.

The tour is in full swing. Tony brings the group to Guan Hoe Soon (www.guanhoesoon.com), arguably Singapore's most famous Peranakan restaurant. They close early, but Tony insists that we absolutely must try Chef Ouyeong's signature desert, Chen Dool, a coconut-cream based ice treat with overtures of molasses and coffee.

Dessert is finished. It is time for the main course. We cross the street to Kim's (www.kims.com.sg), where Tony has pre-ordered the restaurant's famous specialty, my old nemesis chili crab.  This will not be eaten here, but brought down the block to Chili Padi, where a huge spread of Singaporean dishes awaits. Peranakan-style black fatty pork... meat-stuffed cabbage... beef curry... fried yellow noodles... pork and rice sausages...

All that has transpired before this moment has been mere floorshow. This is the main event. Like Muhammad Ali facing George Foreman, I defy my own strategy and attack the meal two-fisted. I wolf down a Kueh Pie Tee (it is kind of a crispy cupcake, only with vegetables and shrimp - very Singapore) and make a beeline for the fatty pork. Then the noodles. A shot at the curry. The sausage. A second Kueh Pie Tee. More sausage. The other diners seem to be tiring, but I am just hitting my stride.

Then Tony opens the box from Kim's, revealing two huge crabs, swimming - nay, drowning - in a fiery pink hot pepper sauce. An American woman reaches for the biggest claw, but with a quick spin of the Lazy Susan I make her settle for second biggest. "Sorry", I say. "This is personal" and savagely shove the claw into my mouth, shell and all.

There is more food on the table, chilli pepper sauce and yellow buns. The rest of the group is exhausted, and I am still eating.  I grab an unwanted hunk of crab. Tony tries to reason with me.

"Your gout!" he whispers. "Remember your gout!"

"I'm controlling it with medication,"  I say, calmly sucking down the last of the decapod's tasty, tasty flesh.

The food on the table is mostly gone, but the tour is not over yet. There is a long walk through yet another housing complex as Tony brings us to a local supermarket where we shop for typical Singaporean after-party snacks.  Beer. Seaweed. Cuttlefish squares. We find a quiet area to consume the last of the snacks under the moonlight as Tony waxes lyrical about the seamier aspects of Singaporean society, namely sex, drugs, and rock and roll.

It is somewhere past midnight, and while the group is still listening to Tony talking about Singapore's gritty side, the tour seems to have stopped. The spice burn has faded into a warm glow.  I remember that there is an English girl waiting for me back at the hostel. She wants me to give her a foot massage. I feel tired. Giddy.  I raise my hand.

"Tony... did I... did I finish the tour?"

"You finally did," he tells me. "You can take off...champ."

As I walk back towards the hostel, I think I hear the Rocky theme floating down from one of the apartment blocks. It must be my imagination.

How to:

The Real Singapore Joo Chiat Foodwalk Eat your way through the Joo Chiat/ Katong district learning about how Singaporeans work, live, play and pray. Sample a diversity of Singaporean cuisines and learn about the Singapore social norms. The tour begins each Thursday at 6:30 pm at the Betel Box Hostel (200 Joo Chiat Road, Singapore). For more information check out http://www.betelbox.com/tour-food.htm.

Kim's Place Seafood Amazing crab prepared however you please. Also serves a huge variety of seafood dishes. (37 Joo Chiat Place; 67-42-1119; open 11 am to 3 am; kims.com.sg)

Guan Hoe Soon Peranakan Restaurant Peranakan cuisine prepared by a master chef, with desserts to die for (38/40 Joo Chiat Place; 63-44-2761; guanhoesoon.com)

Chili Padi Nonya Restaurant Another restaurant serving only the best in Singaporean heritage cuisine. (11 Joo Chiat Place; 62-75-1002; chillipadi.com.sg/Eateries)

Perpetual nomad Joshua Samuel Brown is the co-author of a number of books for Lonely Planet on Taiwan, Belize, Singapore and elsewhere.


The article 'Singapore’s marathon food tour (bring an empty stomach)' was published in partnership with Lonely Planet.