Day 1 — Outback Trails

Morning

Start with breakfast at the Old Airport Road Food Centre, famous for nasi lemak (coconut rice). 

Missing the wide-open spaces? Discover Singapore’s own version of the outback: Pulau Ubin. Catch an amazing sunrise from Changi Boardwalk before crossing over to the small, barely-inhabited island. Take the bumboat from Changi Village (about $2 a person for the 10-minute trip), then rent a bike, and take one of the great bike trails for a glimpse into the kampong days of old Singapore. You may even spot wild boar resting in the forest shade. A cooling beer at Little Island Brewing Company back in Changi Village is a must.

Afternoon

Use the rest of the day to explore Singapore’s heartlands. Try Balestier and Toa Payoh — Singapore’s oldest satellite towns. By now breakfast will be a distant memory and in Toa Payoh you can enjoy some of the best hawker food Singapore has to offer. Try Chey Sua’s Carrot Cake (stir-fried radish cake); Kim Keat’s Hokkien Mee (a noodle dish) and Toa Payoh Lucky Pisang Raja’s Pisang Goreng (fried bananas), to name a few of the much-loved stalls and their offerings. 

Evening

End your day at speed with a trip to the Karting Arena at Turf City. Build up an appetite on the track and round the evening off with dinner at one of the many restaurants near The Grandstand.


Day 2 — Heritage Trails

Morning

Singapore is a master of reinvention, where the contemporary rubs shoulders with the cultural and heritage and hipsters go hand in hand. For a glimpse into Singapore’s past and its modern future, head to cultural precincts like Joo Chiat on Singapore’s East Coast for a taste of Peranakan culture, colourful heritage shophouses and tasty eateries. Check out its newest hotel: Indigo Singapore Katong, and the in-house restaurant, Baba Chews, which is housed in the old police station and serves delicious Peranakan-fusion fare. 

Afternoon

Take a mid day break at Mikeller Bar on Prinsep Street with its many different specialty beers on tap. Then revel in the nearby decorative splendour of Kampong Glam where Malay-Arabic inspired architecture hosts modern day boutiques — or wander along to Waterloo Street to explore the many temples and experience a real sense of the diversity Singapore has to offer. 

Evening

Enjoy live music in the warm night air. Head down to Boat Quay and the nightly musical vibes of Timbre, by the Singapore River. If you prefer to play rather than watch, then wander next door to the Barber Shop where local and visiting musical talents are encouraged to take to the stage. 


Day 3 — Night Owl on the Bay

Morning 

Singapore is a shopper’s dream! Aside from the designer glitz of Orchard Road, there is much to enjoy in the Red Dot’s many local markets. Try the Tiong Bahru area for a great choice of everything, from flowers to clothing. And while you’re there, savour a coffee at the nearby Tiong Bahru Bakery — the salted caramel Danish comes highly recommended. If you’re a serious shopper looking for unique local brands or souvenirs, head over to local design collective Keepers at National Design Centre or Supermama at Singapore Art Museum. You’ll be sure to find one of a kind Singapore-inspired gifts to bring home!

Afternoon

Move from couture to culture at Singapore’s iconic museums including the impressive National Gallery, housed in the former Parliament building near the Padang, to the quirky Mint Museum of Toys on Seah Street. Finish up at the iconic ArtScience Museum (the one that’s shaped like a large hand, but is in fact meant to be reminiscent of a lotus flower) so that you are ideally placed for your evening itinerary.

Evening

Start at one of Singapore’s most eye-catching attractions: Gardens by the Bay. The huge supertrees make for great photographs. If you are looking to visit in the day, book lunch at Pollen (housed in the Flower Dome) and for night owls, the gardens come alive at dusk with a sound and light show. Don’t forget the laser show at Marina Bay Sands — you might also be lucky enough to spot the famous urban otter family of Singapore here. 


Day 4 — Go Local

Morning

Have you been here a few days but still feel you haven’t connected with many Singaporeans? Get the opportunity to experience the everyday lives of Singaporeans and step into the homes of local families for a chat with Tribe Tours

Or check out Tete-a-Tete Language Tables, a regular language exchange where “locals and foreigners gather to exchange stories of life in the bustling metropolis of Singapore”. 

Connect with international-minded locals in everything from Italian to Mandarin, Russian and German, while the kids enjoy yummy cakes at a café — the meet-ups are held at a different eatery each time. Best of all, you can ask for some tips in the language that matters most: Singlish, the local dialect, made up of a glorious mix of Hokkien, Tamil and Malay. Having broken the ice, you can even pick up a few last-minute tips on must-visit spots before you leave, and do them in the afternoon.

Afternoon

Sometimes you need a bit of down time! Relax in the cool oasis of the Singapore Botanic Gardens, a UNESCO World Heritage site. Eat in one of the cafés or take a picnic and enjoy the shade. It’s a great place to people watch too. 

Evening

Head to Chinatown and instead of shopping and eating, consider a walking tour taking in the hidden history of this fascinating area. Travel back in time at Chinatown Heritage Centre as stories are told about the homes of Chinatown’s early residents. Or for a really unusual experience, book a night at the opera at the Chinese Theatre Circle


Day 5 — Island Escapes

Morning

If you and the family are tuckered out from four days of exploring, your final day should be easy on the nerves yet dazzling on the eyes. Start with an early-morning cable-car ride over to Sentosa Island. The ride from Mount Faber onto the leisure island is a scenic highlight not to be missed, so make sure you have your camera ready. 

Afternoon

Once on the island, visit the S.E.A. Aquarium at Resorts World Sentosa. With 100,000 marine animals and over 800 species, it’s a gentle yet fascinating stroll that the whole family will enjoy.

Evening

Finish your itinerary as you have begun — gazing in wonder at the sky. While Changi in the East is the best location for a spectacular sunrise, Sentosa has a bird’s eye view of the west and some of the most magical views of the setting sun — best viewed from Siloso Beach.