Tours to Get to Know Singapore's History
- Stephanie Kolentsis
- Sep 6
- 3 min read
Singapore Living, by Stephanie Kolentsis
Something I’ve always loved about travel and expat life is getting to know a new country and its culture. I’ve lived in Singapore for six years now and know exactly where to find the crispiest kaya toast, but I’ve spent far less time digging into its layered history. With Singapore celebrating SG60, marking sixty years of independence, I’ve been inspired to learn more about how this island became the diverse, cosmopolitan city I love and call home. Tours are one of the best ways to make history feel alive and personal, with guides sharing anecdotes and little-known facts you’d never pick up from a textbook. Here’s a list I’ve compiled if you’d like to explore more of Singapore’s past.
Step Into the National Museum
At the top of my list is the National Museum of Singapore. It’s the country’s oldest museum, covering everything from its days as a colonial trading post to the Japanese occupation through to the modern era. I first visited when I had just arrived in Singapore, but I want to return now that I have a deeper sense of how these major historical events shaped the nation. If you have the chance, join a docent-led tour with Friends of the Museum. Many docents are expats themselves, and all are passionate volunteers who add colourful backstories and context you won’t get from the exhibition alone.
National Museum of Singapore 93 Stamford Rd, Singapore 178897
Descend Into the Battlebox at Fort Canning
For something more atmospheric, head underground into the Battlebox at Fort Canning, a former British command centre. It was here, in 1942, that the British made the fateful decision to surrender Singapore to the Japanese. A friend who went recently said she and her husband learned a huge amount about this turning point in World War II. Walking through the dimly lit rooms and narrow corridors gives the tour a sense of immediacy, and the guide brings the wartime tension vividly to life. It’s the kind of place that lingers in your mind long after you leave.
Battlebox, 2 Cox Terrace, Battlebox, Singapore 179622
Explore Bukit Brown Cemetery
If underground bunkers aren’t your thing, Bukit Brown Cemetery offers another perspective on Singapore’s past. A friend recommended it as one of the best spots for photography, especially at golden hour, when the warm light falls across tombs. Volunteer guides lead walking tours that introduce the lives of Chinese pioneers, community leaders, and families whose legacies are carved in stone. It may sound spooky, but the experience is surprisingly peaceful, a way to slow down and connect with history in the midst of nature.
Bukit Brown Cemetery 36C Lor Halwa, Singapore 298637
Wander Singapore’s Darker Side
If you’re more interested in the parts of Singapore’s history that don’t show up in textbooks, I can personally recommend Uncle Chris’s walking tours. A few years ago, I joined his Orchard Towers walk, and a friend of mine took his Geylang red-light district tour. Uncle Chris doesn’t shy away from the gritty details, answering even the most awkward questions with ease. He also runs a Crime, Murder, and Vice tour that true crime fans will love. These walks aren’t for everyone, but if you’re curious about Singapore’s lesser-known stories, they’re absolutely fascinating.
Uncle Chris's Walking Tours +65 9181 4298
Get a Taste of History in Joo Chiat
If you’d rather learn with a snack in hand, consider the History of Taste tour in Joo Chiat with Veg This City. It’s been on my to-do list since I moved here. The tour focuses on meat-free versions of beloved local dishes and drinks, and takes you through boutique cafés, bustling markets, and off-the-beaten-track restaurants still preserving century-old recipes and techniques. Along the way, you’ll learn about Singapore’s different cultures and hear stories stretching back 200 years — all set against the colourful backdrop of Joo Chiat’s shophouses. It’s an edible history lesson, with plenty of charm and flavour.
Veg This City +65 9793 0270
Singapore may be small, but peel back the layers and you’ll find centuries of stories waiting to be explored. Whether you prefer traditional museums, underground command centres, sprawling cemeteries, the city’s dark corners, or edible history, there’s a tour that will bring the past alive. Whether you’ve been here six days or six years, these experiences will give you a deeper sense of the place we now call home.
 | Stephanie Kolentsis is a learning designer with over 13 years of experience working as an educator across Asia. She’s also an explorer who loves to share her adventures with the AWA community. You can check out her website at www.sklearningdesign.com |
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