i went to Singapore for a carefree getaway and somehow ended up playing a hidden, interactive game of Monopoly around the city.
it was my first proper holiday in two years—and my first real trip since covid. my last holiday had been to europe, which i called my “trip back to memory lane.”
this time, i wanted something different.
i simply wanted to have fun, relax, eat, make very few plans and behave slightly less responsibly than usual.
me, the tourist.
me, the relaxed one.
me, doing the things i never normally get to do.
the last time i had been in Singapore was two years ago, but only in transit. before that, it had been seven years. i had always liked Singapore for its food, safety and cleanliness—and for how everything seemed so organised and efficient.
but this time, Singapore had something rather unexpected waiting for us: a hidden, interactive game of monopoly.
not the kind where everyone sits around a table arguing over who gets to be the banker.
this version was played through a WhatsApp chatbot and took us out into the streets of Katong–Joo Chiat.
the game was self-guided, which meant we could play at our own pace. we could stop whenever we wanted and continue when we were ready. according to the information, it should take somewhere between one and a half and three hours.
we took a little longer than three hours.
apparently, “at our own pace” meant very much at our own pace.
the Katong–Joo Chiat game had 16 questions. there were no dice to roll, no properties to buy and, thankfully, no jail. to move forward, we had to answer each question correctly.
if we got stuck, we could ask for help—but, if i remember correctly, we were only allowed to ask twice.
so naturally, we had to use those carefully.
to begin the game, we first had to make our way to katong–joo chiat and find a small shop that served as our starting point.
but simply finding the shop wasn’t enough.
before we could receive our map and first clue, we had to solve a puzzle.
the game had already begun.
once we solved it, we were given this:
inside, we found Monopoly money, a community chest card, a chance card and a fan, which came in useful as we walked around the neighbourhood.
each item came with clear instructions explaining where and how we could use it. it felt familiar enough to remind me of the Monopoly game i knew, but different enough to make me curious about what was coming next.
you can find the hidden game’s website here.
from there, the clues led us through Katong–Joo Chiat, taking us past small shops, local vendors and historic landmarks.
each correct answer moved us forward and revealed the next part of the game.
it wasn’t simply about reaching the end. without realising it, we were also learning about the neighbourhood.
i would compare it to a quick history lesson—except instead of sitting in a classroom and trying to look interested, we were walking around Katong–Joo Chiat, searching for clues and occasionally questioning our ability to answer what should probably have been a very simple question.
because we weren’t rushing, we had time to stop, look around and notice places we might otherwise have walked straight past.
that was probably my favourite part of the experience.
sometimes when we travel, we focus so much on reaching the well-known attractions that we miss the smaller details in between. this game made those details part of the destination.
after a little more than three hours, we finally completed all 16 questions and reached the end.
our reward was a tote bag with a keychain inside.
i had gone to Singapore wanting to relax, eat, make very few plans and do things i never normally get to do.
instead, i ended up walking around Katong–Joo Chiat with monopoly money in my bag, following instructions from a WhatsApp chatbot and hoping we wouldn’t use our two clues too early.
it was exactly the kind of carefree getaway i needed.
