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Notes -
I expect to be going on a trip (on the order of two weeks) to Singapore fairly soon. Since it will be my first time there, any recommendations for things to see or avoid?
Two weeks in Singapore is kind of a lot. There's not that much to see and while it's a great place to be rich in it's a mid place to be poor in.
For eats, I strongly recommend Blanco Court Fried Fish Noodles and Mr. Biryani.
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I do have to second @pbmonster and ask why you're spending two weeks in Singapore. Perhaps I like to travel fast, but I spent far less time in Beijing, Seoul or Xi'an, all much older and more historically rich cities than Singapore. I honestly say three or four days maximum in Singapore, four if you're really dead from all the walking in the horrific tropical heat; you'll need to rest a lot in order not to pass out from heat exhaustion.
Anyway, I like history, so in my recommendations I'll focus on that alone. Firstly, there are some pretty nice Hokkien temples in the city centre. Thian Hock Keng Temple and Yueh Hai Ching Temple are two relatively old ones (hailing from 1800s) with colourful porcelain detailing and woodcarvings, personally I think you can't go wrong with Hokkien temples; most of them are quite beautifully decorated. Bunch of Indian temples downtown too: Sri Mariamman Temple, Sri Krishnan Temple, Sri Thendayuthapani Temple and so on are some old ones.
Secondly, there are also some historical houses I know of that you can mooch around. The House of Tan Yeok Nee is one of the only two remaining traditional large Chinese mansions left in Singapore, and it's built in Teochew style with a lot of tiling and decoration. And the Former House of Tan Teng Niah is a uniquely colourful Chinese heritage villa. The NUS Baba House on the other hand is a Peranakan/Straits Chinese villa; they're an ethnic group that has both Chinese and Malay descent and hybridises cultural influences from both groups. Worth seeing that when you're in the Straits, because that's an architectural trend you probably won't be able to find anywhere else.
Finally, if you really want a very weird and hyperspecific attraction, the Har Paw Villa is a strange bit of history. It was built by two Burmese-Chinese brothers who developed the analgesic heat rub known as "Tiger Balm" (if you're Chinese, you have definitely had this applied if you have had joint pain or even when you got sick as a kid). They built gigantic theme parks in Singapore, Hong Kong and Fujian showcasing dioramas of Chinese folklore and religion (the one in Singapore features over a thousand of them), which became a popular recreational destination in Singapore. In its heyday during the 1950s and 60s, the park hosted about 1 million visitors yearly, though visitor numbers have significantly decreased now.
Anyway, I'd also recommend making trips to Malaysia, and would point to Malacca and Georgetown as particularly interesting and historical places. I was there just this January, so if you want more info on them I'm happy to provide it.
Thanks for the recommendations! These all look interesting, and quite in line with what I'm looking for. I would add a more specific question for whether there are parts of town that are particularly interesting on the street level, in the sense of having local colour rather than being all globalised slop. (I'm quite open to shantytowns and the like too.) Also, anything touching on the military history of the place? The British colonial era, prisons/bunkers/batteries that changed hands during WWII or were otherwise connected to it being overrun, etc.?
The reason for the ~two weeks is that it's a technically-for-work trip (but with a low expectation for the actual density of work that will be done). A one- or two-day excursion to Malaysia is probably conceivable; how is the transport situation to go to Malacca or beyond? Are there good trains, or is it sensible to rent a car and drive?
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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If you enjoy history, I can recommend the Asian Civilisations Museum. One of the better ones I've visited, specifically it is orders of magnitude better than every single anthropological/historical museum I've visited in Japan. The National Museum is more about Singapore itself, but I also found it well done. If anything, the museums are air-conditioned, which will make them very much appealing once you're exploring the streets. The city also has a nice selection of different styles of temples, I decided to visit all the major ones just as a mission to see many different parts of the city on foot.
If you like Asian food, I've had some of the best Chinese and Indian food of my life in Singapore, both street food and fancy restaurants. Selecting restaurants beforehand is probably worth it.
When I asked Singaporean people what they like to do, they suggested going to one of the mega-malls, with the cable cars to Sentosa Island and (of course) to Marina Bay. The two former I flat out hated, they are not worth doing, unless you really have time to kill or need photos for Instagram - they look much better in photos than in real life. No matter what, absolutely do not go swimming at the beach at Sentosa, that must be just about the worst touristic beach in Asia. Marina Bay (the towers, the gardens, the indoor jungle, the supertrees at night, and the area around it) are more or less obligatory for tourism in Singapore, but just like the main Botanical Gardens and the Zoo I found all that just extremely... mid. Unless you like park design and architecture, it won't even fill a full day.
Two weeks is a lot of time for a "young" city like Singapore. I would strongly recommend long excursions into Malaysia instead of staying in the city, and I regret not leaving for trips sooner.
Thanks for the recommendations! I'll make sure to check out the museums (and the food was ranking high on the todo list anyway, open to concrete (anti-)recommendations there too). Do you know if there's anything interesting to do with the more recent history of the city, specifically including the Japanese occupation?
As I said in my parallel response to problem_redditor, the two-week period is not entirely under my control, but I can probably fit in a short detour to Malaysia somewhere.
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I had a short layover last December.
It's disgustingly hot and humid there year round, so prepare for that.
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