If Clarke Quay is the party central of Singapore, then the Ann Siang and Club Street area is its cool, younger cousin — equally fun and always fully charged with an electrifying atmosphere after dark, a favourite with people in the know of the latest nightlife destinations.

One of the neighbourhood’s most distinct features is the rows of restored shophouses that line its streets. Here, you’ll find yourself at the crossroads of the old and new — the district’s rich history meets hip and trendy shopping and dining options. 

Heritage and history

This charming and bustling lifestyle enclave is located deep in Chinatown — which is no surprise given that Chinatown is Singapore’s top cultural precinct and its second most-visited attraction. Once predominantly a Chinese migrant settlement, the neighbourhood is now a vibrant district that’s home to an array of traditional and contemporary experiences. 

For a taste of the district’s heritage, take a stroll down the pioneer’s trail in Ann Siang Hill and Telok Ayer Green. Meander through the colourful shophouses of the enclave, past iconic landmarks such as the old well on Ann Siang Hill and historical places of worship such as Al-Abrar Mosque, which has been standing since the mid-1850s. 

Visitors can also head to the Musical Box Museum tucked away on Telok Ayer Street. The museum’s home to over 40 antique musical boxes, and is housed in the Chong Wen Ge building, the first educational institution set up by the Chinese community in Singapore in 1849. Be sure to also keep an eye out for the house clan associations in the area, such as the Singapore Hokkien Huay Kuan on Telok Ayer Street, which were first set up by migrants as cultural collectives, and are rich in ethnic history.

Eat, drink and be merry

Eat, drink and be merry

The main draw of the Ann Siang and Club Street area has to be its vibrant, hip dining and drinking scene. Meat lovers should swing by Yen Yakiniku, where you can feast on farm-to-table cuts of Japanese wagyu or American and Australian grass-fed steaks. Or head down the street for no-frills local flavour such as nasi lemak (coconut rice) and otak-otak (grilled fish cake) at The Coconut Club

Explore Club Street when you make a trip to Club Street Social (located on Gemmill Lane). This laidback, brick-walled bistro-bar offers hearty American fare — think pancakes, pizza and pulled pork. For a tantalising menu of Asian food with an innovative twist, hop over to :pluck, where you can chow down on dishes such as tom yum cereal salmon and spicy grilled beef ribeye.

Ann Siang Road and Club Street are buzzing with energy come nightfall — the roads are closed to traffic on Friday and Saturday evenings, with crowds (and maybe even drinks) spilling out onto the streets. Swing by Oxwell & Co for classic Brit bar nosh and tipples while enjoying its rooftop view that overlooks Chinatown.

Shop at niche boutiques

If you’re looking for a spot of retail therapy, the area also offers an eclectic selection of shopping options. Fitness fanatics can head to Lorna Jane to pick out spunky new athletic wear before heading to Level Gym or SLAP Dance Studio (both offer trial and one-off sessions you can easily sign up for) to clock in some cardio. 

All you dapper gents, make an appointment at Truefitt & Hill for their old-school barber shop grooming packages. Then, try Q Menswear on Telok Ayer Street for bespoke fashion items that will keep you at your most stylish. 

You can also stop by Aster by Kyra for something traditional — this niche store carries vibrant Peranakan (of Straits-born Chinese or Malay culture) floor and wall tiles, which make for unconventional, authentic souvenirs. 

Cosy up

Cosy up

After a long day of shopping, dining and exploring, grab some shut-eye and good old R&R at any of the accommodation options in the Ann Siang and Club Street area. Check in to backpacker hostels in the area, such as 5footway.inn at Ann Siang, if you’re looking to travel on a budget (with the bonus option of socialising with fellow travellers). 

Book a stay at one of the area’s boutique hotels. The Scarlet Singapore, for instance, occupies a row of pre-war shophouses on Erskine Road and boasts a rooftop restaurant and outdoor hot tub where you can unwind.  

Alternatively, opt for The Club, a hip F&B-focused hotel. There, you’ll find rooms decked out with bespoke furniture and eclectic décor, alongside Peruvian rooftop bar Tiger’s Milk, fine dining eatery The Disgruntled Chef, and cosy café-bar Mr & Mrs Maxwell. A stay at The Club also puts you right in the heart of the Ann Siang Road hubbub.