Take a hike: Hipsters and hos walk

1. You know about the KTV bars. You know about the hipster cafés like kushiyaki specialist JooJoo (#01-01, 131 East Coast Rd; 6346 7604). And, if you know about that, you should have checked into cheapo beer den The Cider Pit (382 Joo Chiat Rd) by now. Often overlooked, though, are the area’s excellent Vietnamese restaurants like Trang Tiem (196 Joo Chiat Rd) and Quan An Vietnam (233 Joo Chiat Rd). Most characterful, though, is Long Phung (159 Joo Chiat Rd), where you can get among the local diaspora, from homesick Vietnamese students to dolled-up karaoke bar scamps painting their faces and heroically working their modest frames into a respectable bust. Staples like beef pho and goi cuon (summer rolls) make for a light and not-too-bloaty fill before setting off.

2. Turn right and head straight to the end of the road, where Joo Chiat Road is T-ed by Geylang Road, a non-stop throng of heady, multiracial brouhaha that bisects one of Singapore’s raciest red-light districts with every sort of city lowlife imaginable. Not that you’ll notice it yet; the road’s seedy underbelly slowly unravels itself the further east from here you walk. It’s not tits and arse you come across first on this strip, it’s the area’s other main drawcard: durian. Stop off at Fruits Top 1 Department Store (608 Geylang Rd; 6748 9041) and watch as the trading of this misfit fruit is turned into an artform.

3. Further down the road, past Khadijah Mosque (583 Geylang Rd), listless girls in short skirts are a sign you’re nearing the business end of Geylang. On your left, Lor 24A, is an endearing and well-preserved example of the area’s pre-war architecture, with a colourful set of shophouses that are home to the Buddhist Library (2 Lorong 24A; 6476 8435, www.buddhlib.org.sg) and the long-surviving Chinese clan associations, which, dotted around the area, were set up in the 19th century to take in Chinese clansmen fleeing poverty from the mainland.

4. From here, you enter the fray proper: the red-light district begins at Lorong 24 and ends at around Lorong 8. Lorong 12 is one of the more animated people-watching spots: pull up a chair at Kim Yam Kopitiam (275 Geylang Rd) and watch the human flotsam drift by. Alternatively, dip in and out of the Lorongs here and you’ll see brothels of varying degrees of subtlety. The lanes have a palpably stiff atmosphere and for the most part it’s harmless, but don’t take pictures lest you’re mistaken for a member of hubby-catching snitch-site Geylang Checker (geylangchecker.blogspot.com).

5. From here, it’s a heady yomp out of the action into the relatively tranquil Kallang Riverside Park, a largely unsung stretch of grass and riverbank that makes for a neat sidestep out of the toxic spotlight of Geylang. Follow the path down and check out the monument to 19th-century Old Kallang Gasworks, where Rochor and Kallang Rivers meet. Just behind here is superhip, just-opened craft-cocktail bar 13 Wives (#01-02 Ture, 66 Kampong Bugis; 9451 0236, www.13wives.com), which opens on Friday and Saturday nights until 1am.

6. Cross the quaint footbridge, take a quick right-left and you’re on North Bridge Road, which courses directly into the Arab Quarter. Turn down Kandahar Street, where to your left is Sultan Mosque (3 Muscat St), one of Singapore’s grandest. Break right, cut through the pretty gardens of Malay Heritage Museum (85 Sultan Gate; 6391 0450, www.malayheritage.org.sg) and take the south exit towards Baghdad Street.

7. From here, weave in and out of the lanes, and take your pick of cheap eats. New on the block are the excellent Box n Sticks (14 Aliwal St; 6396 4223), which specialises in no-fuss, well-crafted Japanese small plates, and new Mexican cantina Piedra Negra on the corner of Haji Lane (241 Beach Rd; 6291 1297). Alternatively, take stock of the day at hipster dive Ignite (73 Bussorah St; 6395 4335), a popular, boho hangout for Malay skater types that does a wickedly refreshing list of house mocktails ($4.50).