If you’ve been to Singapore before, you’ve probably ticked off the big-name attractions – Marina Bay Sands, Gardens by the Bay, the Merlion.
But Singapore is a city that’s always changing, and there’s plenty to keep repeat visitors busy.
I have visited at least ten times now so I have been able to dig deeper and find some fun and interesting attractions and experiences.
This weekend itinerary is designed for travellers who want to dig deeper, discover new neighbourhoods, try fresh dining experiences, and enjoy attractions that often get overlooked the first time around.
Contents
- Why Visit Singapore Again?
- 2–3 Day Singapore Itinerary for Repeat Visitors
- Day 1 – Exploring Neighbourhoods You Missed the First Time
- Day 2 – Nature, Culture, and Unique Dining
- Optional Day 3 – Even More Local Experiences
- Practical Tips for a Weekend in Singapore (Repeat Visitors Edition)
- Final Thoughts on a Singapore Second Visit
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Why Visit Singapore Again?
I can’t get enough of Singapore and each time I visit I learn about even more things I want to see and do.
Some of those things are new or upgraded attractions that weren’t around during my previous visits.
These can be big-name attractions like the new Rainforest Wild Asia at Mandai Wildlife Reserve, or Singapore Oceanarium, or they could be as small as a new product at my favourite kaya toast place I just have to try.
It’s not just the kaya toast options that change, there is such an interesting and dynamic food scene here in Singapore.
Sure, some hawker stalls are in the fourth generation with the one recipe, but there are also new restaurants and innovations popping up all the time.
Singapore is also becoming an Asian hub for events and you may like to attend one of those.
In the last year or so they’ve had both Taylor Swift and Lady Gaga play multiple concerts, and our most recent visit was because Arsenal (English football team) was playing some pre-season games here.
As a modern city, Singapore is changing and evolving, and there will always be something new and fun to justify another visit.
2–3 Day Singapore Itinerary for Repeat Visitors
In creating this itinerary I have mostly chosen lesser-known activities and attractions, but if you missed something on the first trip (it took me 10 visits before I had a Singapore Sling at Raffles!) you can swap things in and out.
Weekend in Singapore – At a Glance
Day 1 – Explore neighbourhoods you missed
- Breakfast in Joo Chiat or Katong
- Street art + boutiques in Kampong Glam
- Afternoon tea or cocktails at Atlas Bar
- Sunset dinner at Level33 or rooftop drinks
- Night-time light show at Gardens by the Bay or live music at Clarke Quay
Day 2 – Nature, culture & unique dining
- Morning walk along the Southern Ridges or cycling on Pulau Ubin
- Lunch at a hawker centre
- Museum visit: ArtScience, Peranakan, or something quirky
- Dine by the water, on the Singapore flyer, or at a themed restaurant like Absurdities
Day 3 (Optional) – Cafés, spa & relaxed exploring
- Stroll through Holland Village or Tiong Bahru
- Boutique shopping or brunch
- Afternoon tea at the Fullerton or a spa session before your flight
Want to save this list? Click here to download it as a pdf.
Day 1 – Exploring Neighbourhoods You Missed the First Time
Start your weekend in Singapore by heading east to Joo Chiat and Katong, a colourful mix of heritage shophouses, Peranakan culture, and fantastic local eats.
This is the area I stayed in during my first visits, and it’s not the shiny side of Singapore you’re used to – although it has become more upmarket with cool coffee shops and boutique shopping options dotted between the nightclubs and local stores.
Sample laksa or kaya toast at a neighbourhood café (Chin Mee Chin Confectionery is a popular option) before moving on to Kampong Glam.
Here, you can browse indie boutiques, explore the Sultan Mosque, and spot vibrant street art – the perfect way to see a different side of Singapore.
After exploring the laneways, head across the road to the Atlas Bar, regularly listed as one of the world’s top bars – like here where it’s number 43.
Relax here with a cheeky cocktail, or if you organise it in advance, a tasty traditional afternoon tea.
From Kampong Glam, head to the Marina Bay area, but take your time getting there.
Stroll along the waterfront via the Helix Bridge as the sun goes down, straight towards your dinner stop.
Enjoy Level33, the world’s highest urban microbrewery, for dinner with a view. Have a tasting paddle or a local craft beer, and choose from modern European dishes or share plates.
Afterwards, wander back to Gardens by the Bay for the light show. Even if you’ve been before, the themes change often, so it’s worth seeing again, especially from the OCBC Skyway.
Alternatively swap the lights for nightlife and head to Clarke Quay for a riverside drink and live music.
Day 2 – Nature, Culture, and Unique Dining
Start today swapping the skyscrapers for green views with a morning walk along the Southern Ridges or a cycling trip on Pulau Ubin, where kampong life still exists.
Both of these will show you a different, greener, side to Singapore.
Have lunch at a hawker centre you haven’t tried yet, or instead, go back to one you HAVE tried and relive to nostalgia of your last trip to Singapore.
In the afternoon, visit one of Singapore’s museums or galleries for a quieter cultural fix.
There are so many different options here, from the funky ArtScience Museum, to the National Gallery, Changi Museum & Chapel or the Peranakan Museum.
You could even get your Insta star on with a visit to the Museum Of Ice Cream or Madame Tussauds.
Finish the day by treating yourself to a memorable dining experience – perhaps a seafood feast by the beach at East Coast Lagoon Food Centre, dinner on the Singapore Flyer or even while cruising the Southern Straits.
For something truely unique and fun you could try the restaurant Absurdities – which really does promise to be memorable.
Optional Day 3 – Even More Local Experiences
If you’ve got an extra day in Singapore, explore Holland Village or Tiong Bahru, both known for their café culture, boutique shopping, and laid-back vibe.
Treat yourself to afternoon tea at the Fullerton Hotel or a spa session before heading to the airport – a relaxed end to your second visit.
Practical Tips for a Weekend in Singapore (Repeat Visitors Edition)
Stay in a different neighbourhood
If you’ve always stayed in Marina Bay or Orchard Road, switch it up this time. Base yourself in an area like Joo Chiat, Kampong Glam, or Tiong Bahru to see a different side of the city and explore new cafés, shops, and street life right on your doorstep. Check current Singapore hotel deals ➜
Use the MRT and Grab
The MRT is fast, clean, and incredibly easy to navigate – plus it’s often quicker than taxis in traffic. For places the MRT doesn’t reach easily, Grab (the local rideshare app) is cheap and reliable.
Book ahead for popular spots
Even as a repeat visitor, you’ll still want to tick off a few big-name experiences. Book attractions, tours, or special meals in advance — it’s the best way to avoid queues and make the most of your limited time. See what’s available on Klook ➜
Try a themed walking tour
Skip the generic city tour and choose something quirky or niche – from street art walks to night-time food tours – so you can see familiar streets with fresh eyes. Browse guided tour options here ➜
Time your visit with an event
Look out for festivals, concerts, or seasonal light shows you’ve never seen before. Chinese New Year, Deepavali, and the Singapore Grand Prix each transform the city in their own way.
Final Thoughts on a Singapore Second Visit
Singapore rewards curiosity.
Even if you’ve already seen the headline attractions, there’s always a new café to try, a street mural you haven’t spotted, or a cultural experience waiting just off the main tourist trail.
Use this itinerary as a starting point to plan your next weekend in Singapore, and you’ll leave with a fresh perspective on a city you thought you knew.
Now’s the time to book your hotel, reserve those unique dining spots, and make the most of your return visit.
TRAVEL PLANNING ESSENTIALS
Find flights – I always use Skyscanner as my starting point when searching for flights. One search will give many options including airlines I may not have thought of. This means I can find the best possible flights to suit my needs
Book accommodation – my go to is always Booking.com for the best places to stay. It’s not just hotels anymore, but hostels, apartments, B&Bs and more. I love that the bookings are usually cancellable, and that I can book now and pay later.
Hire a rental car – RentalCars.com is my go to here. It allows me to do just one search and it finds cars from many of the different supplies, so no checking multiple websites to compare.
Get travel insurance – you would have heard by now that saying “if you can’t afford travel insurance, you can’t afford to travel”. If we’ve learnt anything from the last couple of years it should be how essential travel insurance is. I use CoverMore for my insurance.
Pick up an eSIM – I tried an eSIM on my last trip and it was fantastic. I set it up before I went so it was ready as soon as I landed, and I still had access to my home number for emergencies. Get your own eSIM at Airalo.
Book activities, tours & attractions – I use a few different websites for this. Viator and Get Your Guide tend to be the first places I look. In Asia, Klook often has more options, and in Australia it’s Experience Oz.
Manage your money – the best way to manage your different currencies is with an account from Wise. You can hold money in many different currencies, and use them with the ATM card or from your phone.
