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Day 1

1 Tiong Bahru

Recently revived by an onslaught of trendy outlets and plush high-rises, Singapore's oldest neighbourhood's nostalgic charm and old-world allure still linger on through the art deco pre-war shop houses, time-honoured eateries and lush pockets of nature that beg an afternoon of exploration with the family.

2 National Museum of Singapore

For a truly immersive trip back to the Singapore of yesteryear, the city’s oldest museum warrants a visit with your loved ones. Inside its elegant neo-classical structure lies a compelling narrative that will take you on an intriguing journey from the past to the present through interactive exhibits and culturally-important artefacts. 

The Foothills
3 The Foothills @ Fort Canning Park

Once the Headquarters of the British Army Barracks, Fort Canning Park is an iconic hilltop landmark that has survived to tell many tales. Now not just a venue for international concerts and theatre productions, its foothills play host to various restaurants and a gallery that make for a relaxing evening stroll.  

Day 2

Peranakan Museum
4 Peranakan Museum

Although Penang and Malacca are the epicentres of Peranakan culture, this museum is worth a visit for its fascinating displays and fun-filled activities for your kids. Reputedly housing one of the world's finest and most comprehensive collections of Peranakan objects, it complements what Malaysia already has to offer perfectly.

Joo Chiat/Katong
5 Joo Chiat/Katong

Besides taking a closer look at the intricate and colourful designs of the Peranakan buildings here that will provide you with different perspectives from those found at home, drop by the OH! Open House – a series of intimate art exhibitions hosted by owners and residents of these beautiful spaces over weekends in March.

Sinpopo Brand
6 Sinpopo Brand

This hidden gem serves up a delicious selection of savoury dishes and classic desserts that evoke a good dose of nostalgia with an innovative, modern twist. Its assorted vintage paraphernalia and ultra-retro atmosphere make it a favourite hangout amongst the young and old who still yearn for a taste of the past.

Day 3

Ann Siang Hill
7 Ann Siang Hill

Formerly the home ground of traditional Chinese clan associations and exclusive social clubs, this delightful little area is now a haven for family-friendly restaurants and al fresco cafés. At night, the street comes to life with cool concept bars and pubs; and is closed off to traffic for the wandering (and thirsty) pedestrian every Friday and Saturday evening.

Club Street
8 Club Street

Interconnected with Ann Siang Hill, the elegantly restored retro shop houses on this street host chic boutiques and quirky stores for a fun-filled afternoon of souvenir-hunting with your nearest and dearest. There are also many places to stop by for a coffee break or that cheeky beer afterwards.

Dempsey Hill
9 Dempsey Hill

Come dusk, the lush greenery and resort-like ambience of Dempsey Hill make it the perfect place to chill out and grab some grub with your loved ones. Besides a wide variety of dining establishments and watering holes, this former British army barracks also offers many opportunities for you to indulge and unwind in the form of shopping and pampering.

Day 4

10 Haw Par Villa

Many older Malaysians would have memories of being brought here as kids and scared into behaving their best at all times – or face the gruesome consequences on display. Famous for its hair-raising depictions of 'hell', this 77-year old park now provides free entry and guided tours for a morning well spent with the children.

11 Labrador Nature Reserve

After all the chills, get some fun in the sun with your loved ones by exploring a wonderful world of flora and fauna to uncover intriguing pieces of the past such as war relics, forts and secret tunnels. Previously an ‘impenetrable fortress’ for the British, this park is presently the perfect spot for some scenic relaxation.

Gillman Barracks
12 Gillman Barracks

With its conserved colonial architecture and lush surroundings, Gillman Barracks is an inspirational arts cluster that will stir the imagination of you and your loved ones. Tucked away from the city centre’s hustle and bustle, it was once the site of a fierce battle between British and Japanese soldiers during World War II and now features the ground-breaking works of both established and emerging artists.