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Notes -
That does exist in places (I look for these kinds of neighbourhoods as well; I truly hate the International Style). You'll find a lot of lovely colourful Straits-style shophouses in and around Chinatown, which also happens to house the two traditional Hokkien temples I spoke about earlier. In addition, Little India should provide you much of that local vernacular style, there are many shophouses there that primarily cater to the Indian diaspora. Koon Seng Road also features a bunch of Peranakan dwellings that have been painted very colourfully, though there isn't that much else to do in the area.
There are a good number of colonial-era WW2 forts and bunkers: the most prominent are Fort Siloso, Labrador ATMB Battery, and the Battlebox on Fort Canning Hill (the Battlebox, in particular, is where the decision to surrender Singapore to the Japanese was made). Fort Canning also has some earlier fortifications going back to the 1800s, though only the gate and two cannons remain of this early fort. There's also the Changi Chapel and Museum, which features exhibits on a strange part of WW2 history: it was a place where Allied POWs were interned during the Japanese occupation of Malaya, and during this period prisoners converted buildings into churches and built makeshift altars out of scrap.
By the way don't forget to try the Singapore chilli crab. Criminal thing to miss out on, in my opinion.
There's no direct train from Singapore to Malacca, and it's a three-hour drive between the two cities if you're using a rental. I believe there are also buses directly connecting the two cities, that's a four hour trip.
In other words, it's doable if you're willing to spend a bit of time on the road. Ideally I would spend two full days just to soak in the vibe, though I'm not sure how realistic that is for you depending on your schedule. Malacca is small and sleepy but very charming, it has all the local feel you would want from a Southeast Asian city (it's so colourful and vibrant it looks like a Wes Anderson film sometimes), and has the historical credentials to boot, having been founded around 1400 as the capital of a sultanate. Lots of pretty little temples, heritage houses, churches, mosques and fortresses. It also has the most consistently amazing food I've tasted in the whole country, and I do not say this lightly; I grew up in Malaysia and am very particular about my Malaysian food.
If you end up deciding that you want to do Malacca just let me know. I can offer up some very detailed recommendations.
EDIT: Note that NUS Baba House seems to be closed for renovations, for something similar to that there's also the Singapore Peranakan Mansion Museum.
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