Ann Siang After Dark, from the Gallery Roof

Start on the roof of the National Gallery as the light goes, with the Padang turning gold below you and the bay beyond it. From there you walk south across the river to Ann Siang Hill, where the cocktail bars sit in shophouses, the narrow old terraces built with a shop downstairs and a home above. The best rooms on this route are small and they fill, so book your Chinatown bar for around 9pm before you set out.

Clarke Quay, a short way upriver, has a job of its own. It's lit in bright colours, with touts at the restaurant doors and a 7pm river cruise for first-timers, and it does all of that loudly. This route keeps to the quieter streets on either side of it, where you can hear the person you came with and the drinks are the reason you're there.

The Gallery roof at sunset

The Gallery stays open until 7pm, with last admission at 6.30pm, so go up to the roof decks while it's still light. The Padang is laid out below you with the bay beyond, there's no DJ to compete with, and your first drink can wait for the next stop. From City Hall MRT, take Exit B. On the Grand Prix weekend, 9 to 11 October, the Padang is fenced off for concerts, so start in Chinatown instead.

A martini at ATLAS

Next comes ATLAS in Parkview Square, up by Bugis MRT, so take a taxi from the Gallery. It's a three-storey Art Deco lobby built around a tower of gin, with a spiral staircase that turns up in everyone's photos. One martini makes it a visit. Three, and you'll be piecing the evening back together on the ride home. If ATLAS is booked a month out, Manhattan Bar at Conrad Orchard is where we'd go for a martini instead.

If you'd rather stay up high, CE LA VI SkyBar at Marina Bay Sands is 57 floors up, and the cover includes one house pour. Lantern at Fullerton Bay needs a booked slot if you want a seat by the water, and its pool is for hotel guests. We'd choose one skybar a night and spend the rest of it at street level. LeVeL33 at Marina Bay Financial Centre is a brewery 33 floors up, listed as the world's highest microbrewery in a building, and a pint at the bar costs less than the brewery tour.

Along the river to Boat Quay

From ATLAS, take a taxi back down to the river, then walk. Getting from the Civic District waterfront to Chinatown takes 15 to 20 minutes, either along the river or through Telok Ayer, and on foot you get the river lit up at night. The river way passes the Old Hill Street Police Station, whose 227 coloured windows look best from the water. The Arts House is next door.

Anderson Bridge is part of the F1 track on race weekend and a good crossing at dusk for the rest of the year. Walk it towards Boat Quay, the original curve of shophouses on the river, built for the old river trade and now lined with tables along the water. Stroll the waterfront, then find your drink one street back.

Ann Siang Hill and Club Street

Ann Siang Hill and Club Street start to wake up at 6pm and are lively by 7.30pm. Walk the slope once before you choose, and pick a door that isn't the loudest on the street. A few streets over, Keong Saik has three blocks of restaurants in shophouses that were once part of the red-light district. Book a table there; wandering the street costs nothing.

Duxton Hill, in Blair Plain, is quieter again, which is why the chef's table dinner sits down there at 7pm. If you want a sit-down meal before the bars, that's the one we'd book. Eat before you drink or after, but make sure you eat.

The small cocktail rooms

Book these ahead. Native is a regular on the Asia's 50 Best Bars list, in a tiny Chinatown room, making drinks from leftover fruit and obscure distillates. It works better than it sounds. Jigger & Pony, another 50 Best name, is in the Amara hotel on Tanjong Pagar Road and pours negronis in a grown-up room. A booking at either for around 9pm gives the evening its anchor.

If Native is full, Employees Only is another tiny room, a New York import that feeds you as well, so walk in early or book ahead.

On Bukit Pasoh, Gibson is the Jigger & Pony Group's martini parlour, one floor up in a 1930s shophouse. Start with the Gibson itself, and book ahead.

Nutmeg & Clove builds its drinks on Singapore ingredients. It's on Purvis Street near Bugis MRT, at the ATLAS end of town, so it pairs with your martini at the start of the night rather than with the Chinatown rooms.

For something slower, Auld Alliance pours whisky in a clubby attic room above a French restaurant. If you're over on the Orchard side of town, The Other Room is a whisky room tucked behind the Marriott Tang Plaza, and you'll want a booking.

28 HongKong Street is an unmarked shophouse bar on the Boat Quay side of the river, so it sits right on the walk; book ahead. If you'd rather be led, the Chinatown cocktail crawl meets at Chinatown MRT Exit A at 8pm and takes you through three shophouse bars and their signature drinks, on foot from Amoy Street to Bukit Pasoh.

A bay night instead

On a wet night, the lotus-shaped ArtScience Museum makes a good swap. After Hours runs on Fridays and Saturdays until 9pm, with last entry at 8.15pm, and Into the Ocean: Journey Beneath fills the Basement 2 galleries until 1 November. Afterwards you can walk round to Event Plaza for Spectra.

Spectra, the light and water show over the bay, plays at 8pm and 9pm from Sunday to Thursday, plus 10pm on Fridays and Saturdays. It lasts 15 minutes, costs nothing and needs no booking; at weekends, get there 15 minutes early. Marquee, the nightclub with an indoor Ferris wheel, is ticketed, and its weekends sell out.

For a night when a film is the point, Filmhouse, in the old Projector halls at Golden Mile Tower, is the cinema we'd choose; check which hall your film is in.

Robertson Quay upriver

Robertson Quay, upriver from Clarke Quay, is the quieter stretch of the river, with good restaurants along the water and a riverside path to walk off dinner. STPI, the print and paper gallery at 41 Robertson Quay, is free and open until 7pm from Monday to Saturday.

The Museum of Ice Cream has moved away from the quay to 100 Loewen Road in Dempsey. It's open daily from 10am to 6pm, with last entry at 5.45pm, so it belongs to another day.

Horror Nights on Sentosa

Halloween Horror Nights 14 at Universal Studios is a night of its own if a scare is what you're after. It runs on select nights until 1 November, from 7.30pm to 12.30am, with tickets from S$68 on non-peak nights. A Universal Studios day ticket doesn't get you in, and it isn't recommended for under-13s. The queues are on Sentosa, and so is 1-Altitude Coast, a rooftop pool bar at the Outpost Hotel, both a taxi ride from Chinatown.

Supper after the bars

Supper, the late meal after a night out, is easy to find nearby. Satay Street takes over Boon Tat Street beside Lau Pa Sat on weekdays from 7pm to 3am, with nine carts grilling; you pay at each stall. Gluttons Bay, outside the Esplanade, serves its satay on the waterfront, open Monday to Thursday from 4pm to 11pm with last orders at 10.30pm. For a late plate closer to the bars, head for the zi char on Smith Street, where the cooks turn out big shared dishes to order.

Another late plate near the bars is Neon Pigeon on Carpenter Street, an izakaya, the Japanese kind of pub that feeds you as you drink, pouring highballs with small plates. It fills up, so book or go early.

If you're still hungry when the roofs empty, Swee Choon has been making dim sum since 1962 at 183–193 Jalan Besar, a 15-minute taxi from Ann Siang. It's open every day, and from Sunday to Thursday the hours are 7am to 2am, with last orders at 1.30am. On Fridays and Saturdays it runs until 4am, with last orders at 3.30am, and it also stays open until 4am on the eve of a public holiday. By then the street's hardware shops are shuttered and the steamers are going.

The night ends when the roofs empty and Telok Ayer is just a street again. Up the river, Clarke Quay stays lit like a theme park, and it manages fine without your help.