chinatown singapore

Last Updated on October 6, 2021

As we mentioned in our previous post on Singapore, this Southeast Asian city-state was a bit of a mystery to us. For everything we learned during our treks through the city, there were ten more questions as Singapore unraveled before us. We realized that we needed professional help – it was time for a Singapore walking tour. Recommended #1 on Tripadvisor was The Original Singapore Walks, so we decided to join their Secrets of the Red Lantern Chinatown walk.

walking tour singaporeThis was by far the best walking tour we have been on yet. It was saucy and racy and gritty and fascinating.

Bathroom buckets and sardine packed apartments 

Set in Chinatown, we learned the history from the perspective of the Chinese immigrants who flooded to Singapore’s shores in search of opportunity after British businessman Sir Stamford Raffles founded the city-state in 1818 as a trading post for the East India Trading Company. The Chinese who arrived here throughout the 19th century had often endured high seas for months at a time, were penniless, starving and often many friends or family members had died on board the ships. When they arrived to Singapore they were initially given assistance by others who, in their demands for payback, would essentially ensnare them into a form of servitude impossible to escape (similar to the concept of sharecropping in the U.S. South).singapore chinatownOur guide Janet shared the stories of the shophouses, which had factories or shops on the ground floor and 20-30 people living upstairs in one-room apartments. Some had wooden planks as beds, others just the floor, and even these spaces were often shared between those on day and night shifts.

Near the start of our Singapore walking tour she took us into a back alley (which in today’s Singapore is surprisingly clean) to show us little doors in the backs of the shophouses. Stinky buckets of number 1 and number 2 were placed behind these doors, and trucks would come, open them and collect the waste each day. From her explanation and our own imagination we could practically smell the stench of these overcrowded houses and their appalling living conditions.

chinatown singapore

Picking your poison in Singapore

Working conditions were no better, she told us, and the only break the immigrants here could get from the backbreaking labor was in the brothels and opium dens. The opium dens were where the physical pain could actually be lifted for the little while they could smoke. Chinatown was the epicenter for brothels as well, and we learned how to recognize some of the ‘higher class’ establishments, the division among the Chinese and Japanese prostitutes (the latter served only Europeans while the former focused on locals).

Much of the area has long since been gentrified and legal prostitution all but phased out, but she did sneak us past one of the last few remaining legal brothels and we had a sneak peak as we passed. It was a small entrance in a back street that just looked clinical, unlike the roaring scene she described along the way. Janet showed us many of the ‘materials’ used (see below).

chinatown singapore feminine oilSexual liberation in Chinatown eventually led the area to become the unofficial home of Singapore’s gay community – a complicated issue itself. Essentially homosexuality is frowned upon, sex between men is illegal, and yet up until recently Singapore hosted one of the world’s largest gay festivals each year. We really appreciated Janet’s candor about the gay community.

She provided the kind of in depth information that we normally only experience on LGBT-focused tours, even stopping under a rainbow flag waving at one of the more popular gay bars in the city. It was great to see the wealth of information included on the tour about the gay community, even though everyone on the tour but us was definitely straight.

chinatown singapore with gay barWhat we loved about Janet was that she clearly had great relationships with people in the community. We stopped at a Chinese medicine shop and chatted with the owner who supposedly supplied President Bill Clinton with a natural form of a special elixir (think snakes and bugs floating in an liquid meant to…raise the roof…).

She gave us a great advice on where to eat vegetarian Chinese food, which we took and it was delicious! And even though she couldn’t take us in to tour the brothel, it wasn’t for not trying. Singapore Walks actually tried to reach out and create relationships with some of them in order for tours to be able to experience first hand how the brothels work today. Apparently this didn’t go to well…but they tried.

singapore chinatown chinese medicine shopShe left us with this little nugget: back in the day people used to joke that Singapore was just one letter off. Replace the ‘p’ with an ‘l’ and you get the true name of Singapore in the late 19th and early 20th centuries: Singalore – Sin Galore.

From our drinks at the top of the Marina Bay Sands hotel looking down over the city  in 2012, we would have never known about Singapore’s seedy past, and it was loads of fun finding out all about it.

singapore sunset from top of marina bay sands


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Tags : singapore


    1. There are grittier sides of the city, for sure, but in general it is now squeaky clean compared to other cities. It’s a wonder how it became this way, though, when you really look at how seedy it once was!

    1. Definitely see where you’re coming from, but the tour really opened our eyes to a side of Singapore we would have never otherwise known about!

  1. We did our own walking tour through Chinatown last night. I was surprised to read it was the heart of Singapore’s gay community too. I did love that the Buddha Tooth temple was covered in rainbow flags! Not sure it was intentional though but still made me smile.

    1. We were surprised to find out there has been an establish gay community for so long there, we thought it would be much more underground than that! Glad you had a great time in Chinatown.

  2. Very interesting history there in Singapore. Makes me very grateful that I didn’t have to live and work during that time. The smell had to be awful and the work tough. Conditions weren’t the best. Interesting how this community became the place for the gay community here.

    1. Jeremy – the SMELL, that is what I was thinking of the whole time, too. Can you imagine? 40 people to an apartment and buckets serving as toilets. And in that heat….oh man!

  3. I’ve seen some bloggers pooh-poohing organized tours like this, but I love getting the inside scoop on dirty details you might not ever discover when wandering on your own. Sounds like Janet was a great guide!

    1. When I was younger, I would have pooh-poohed it too. But tours like this offer so much information, so much hard work and research went in to create this, I think it’s silly to pass up an opp to know more, especially in a place with such rich history! Thanks for ‘getting’ that Bret! 🙂

  4. I spent a month in Singapore a few years ago and loved it. I wish I’d know about this tour you went on. It sounds fascinating. I did go to Orchard Towers, better known as the “Four Floors of Whores”. Now that was something to see. Talk about Sin Galore. I’m going to have to write about that one day soon, I think . 🙂

    1. If you go back, definitely check out The Original Singapore Walks – they have all kinds of tours. A month in Singapore, though, that’s amazing. We would definitely want to do that. Accommodation was the biggest factor for why we didn’t stay longer – it’s pricey! It would be great to know where you stayed for a month!

  5. I lived next to Chinatown for a year and didn’t know half of this stuff! Sounds like the walk is something to look into if I ever go back to Singapore!

    1. You should, Cole – We learned so much on that walking tour and we’ll take another one for sure next time we’re in town.

  6. I’m convinced it is still a seedy dodgy city. The authorities try to make the place seem so clean and ordered, but how could that be possible with the kind of history you’ve described?

    1. I think Singapore did a great job transforming itself – other cities that were a bit seedy in the past (London, New York, Paris…) were also able to turn around, but I think no city did it as fast as Singapore did.

    1. This one really was great! We love it when a city offers free walking tours, led by locals- you always learn so much in them and you only have to tip the guide. Well worth it in cities like Berlin, New York or San Fran 🙂

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