Bar crawl: Orchard

Begin your night at this swish lounge, in Regent Singapore, that puts most other hotel bars to shame. Top spot on this year’s Asia’s 50 Best Bars list notwithstanding, Manhattan has made a name for itself for its unflinching recipe: take cult and craft American spirits, mix with a do-it-yourself ethic that has seen bartenders barrel-age liquors and infusions on the premises, and garnish with a gorgeous leather-bound and marble-lined space.

Order the namesake cocktail ($25), which is one of head bartender Philip Bischoff’s signatures – he uses Michter’s US1 Straight Rye whiskey, housemade cherry brandy, vermouth and Angostura bitters. There on a Sunday? Its cocktail brunch ($150) lays out a spread of classic New York nosh and an unlimited supply of libation. 

Consider yourself the next Hemingway or Faulkner? Then make your way to The Writing Club, a gentlemen’s club-esque whisky bar. Knock back drams of rare whiskies from its 500-bottle-strong collection, including single-malts from independent bottler Hunter Laing’s First Editions Authors’ Series, which celebrates the likes of Victor Hugo and Charles Dickens. Dreaming up your next bestseller will be easy in the bar’s plush leather sofas, with a glass of liquid inspiration in hand, of course. After all, even the literary greats wrote drunk – just be sure to leave the editing for another day. 

Step behind the curtain next to the entrance of Uma Uma Ramen and follow the staircase down into The Horse’s Mouth. The colourful display of origami flowers and hanging paper lanterns should clue you into the fact that you’ve entered a Japanese cocktail bar. And the menu will quash any remaining doubts – the cocktails showcase various Nihon ingredients and sake labels you won’t find anywhere else on the island. Once you’ve had your share of revelry, exit via the secret door and you’ll find yourself back on Orchard Road for easy access to your next stop.

A boundary-pushing speakeasy is probably the last thing you’d expect to find in a straight-laced hotel like the Marriott, but behind a door that easily blends into the rest of the wall lies The Other Room. Bartending extraordinaire Dario Knox doesn’t believe in labels, so don’t expect to find a bottle of your favourite spirit here. Instead, Knox ages and finishes everything in various casks. Order a flight of whisky, rum, gin or whatever your choice of poison may be and select the one you like best. He’ll then whip up a cocktail with that spirit, tailor-made just for you.

By now, your head’s spinning and your belly’s aching for some grub. So stumble into Concorde Hotel and muster up the energy to find this boisterous hole-in-the-wall. Izakaya Tamako is a cosy – read: tiny – Japanese bar that’s big on hospitality. The hostess typically plies you with Sapporo, sake, soju or makgeolli, while the yakitori man is glad to play drinking games with you while flipping skewers on the grill. (Head’s up: you’ll lose.)