Lee Shu ShienTokyo in 2025 continues to redefine the boundaries of fun, craziness, and downright bizarre challenges. Beyond the typical sightseeing spots, the city now offers an even more mind-blowingly awesome array of experiences that push you out of your comfort zone and deep into the heart of Japan’s eccentric culture. Whether you’re a thrill-seeker, a foodie with an adventurous palate, or simply someone looking for unforgettable stories to share, this list of 20 challenges dares you to immerse yourself in Tokyo like never before. Don’t come home until you’ve checked off every single one!
Also read: 5 Unique Theme Parks in Japan You Absolutely Need to Visit
1. Jumbo gyoza food challenge
Image credits: Ikukotonogi via X
“Jumbo” is an understatement. You’re looking at 2.5kg of gyoza, or an equivalent of 100 regular ones! Finish it in 60 minutes or be ready to fork out a whopping ¥9600 (S$84)!
2. Hold your breath and try natto
Image credits: Hiroshi Yoshinaga | Flickr
The durian of Japan, natto is well-loved by the locals but shunned away almost unanimously by foreigners. Challenge yourself to a bowl of steamed rice topped with these slimy fermented beans. Remember to hold your breath.
3. Get naked in an Onsen
Image credits: Macaron Magazine | Official Website
From all-night singing to getting naked – wow, that escalated quickly!? Well to be fair, we don’t mean naked out there on the busy intersection of the famed Shibuya crossing. Get naked and really really comfortable in Japanese public bath houses. It’s a good exposure (ha-ha) to traditional Japanese culture!
4. Go porn-shopping at the 7-storey adult shop
Image credit: BJect via Wikimedia Commons
Grab some adult toys as souvenirs for yourself from M’s. Yes, here is where you get to buy the infamous life-size doll! You lose if you’re shy! Apparently, if you try on a costume and let the staff take a picture of you in it, you get 20% discount on your purchase. Don’t say we never share good lobang.
5. Make your own food samples
Some of you might have seen this viral video making its rounds on the internet some years ago. Why not get your hands down to making similar food replicas? This is a fun family-friendly challenge that is perfect for kids too!
6. Enter Fuji Q’s haunted hospital, alone
Image credit: Autopilot via Wikimedia Commons
What’s a challenge without some terror! We dare you to walk Fuji Q Highland’s most popular attraction, The Haunted Hospital, alone. FYI, it’s a one-hour long walk in a disused hospital that involves blood-soaked nurses, disfigured men in white, crawling zombies and plenty of screaming.
7. Sing karaoke for the entire night
Image credit: Jimmy Alvarez | Flickr
Sleep is for the weak! Stay awake and sing until your voice turns hoarse the next morning at 24-hour karaoke bars in Tokyo. They’ve got an endless database of English, Mandarin, Japanese and Korean songs for you to jam to, it won’t be difficult to keep your spirits up throughout the night.
8. Squirm as you eat at The Vibe Bar Wild One
Inside this vibrator bar – yes, a vibrator bar – the elaborate decorations you’ll see are, unlike its name, nothing close to subtle. Obviously, we can’t show a photo of the bar on here, so just trust us on this and find out for yourself!
9. Take lots of neoprints wearing a fancy costume
Image credit: Lee Shu Shien
Don’t forget the “V” sign, a kawaii expression and lots of cute stickers. Put your pride away ‘cause you be doing it the Japanese way! Cheese!
10. Visit Meguro Parasitological Museum
Image credit: Guilhem Vellut | Flickr
Does the above image of parasites make you feel uncomfortable and sick in the stomach? Well, that’s the point of a challenge. For the record, the second floor houses a display of an 8.8m-long tapeworm extracted from a 40-year old man. Yikes.
11. Ride the world’s steepest roller coaster
Featured in Guinness Book of World Records as the world’s steepest roller coaster, Takabisha is located about an hour away from central Tokyo in Fuji-Q Highland. Enjoy Mount Fuji in full glorious view before an almost-perpendicular free fall (121° to be exact!) that is sure to make your heart skip a beat! Get that thrill by watching this POV:
12. Stay in a themed love hotel
Image credit: Hotel Alpha In | Official Website
For the fanciers of.. well… being tied up, Hotel Alpha In is where your fantasies come true. Take your pick from “Medical Style” rooms, “Shame Style” rooms, “Space Style” rooms and more. If you think you’re flexible, try the “All Purpose Style” room.
13. Eat shirako
Image credit: Chris Chen | Flickr
In layman terms, it’s sperm sac. Have you got the balls (ha) to try this? Rule: no squirming while eating. Itadakimasu!
14. Slurp on ice-cream cone ramen
Image credit: Kishyoku | Official Website
Japanese are definitely nothing short of experimental when it comes to food!
15. Let snails roam freely on your face
Image credit: Hthrd | Flickr
Snail facial is all the rage now! But why resort to Tony Moly facial masks when you can have the real thing slithering down your cheeks? It doubles up as a facial massage too.
16. Try nyotaimori
Image credit: Edith Soto | Flickr
Nyotaimori (body sushi) involves eating sushi from a naked woman on the table. This dining experience, however, should not be assumed as a common tradition in Japan. It is hardly found in Tokyo (to the relief of feminists), but some reckon that you may chance upon such a service in Roppongi.
17. Try a real datsu-shitsu game
Image credits: Super Escape | Official Website
Put your nerves and wit to test with a real-life room escape game. The theme of the game ranges from prison to dungeon, but whatever the setting is, solve mysteries and obtain clues to get out as soon as you can!
18. Chew on meat sashimi
Image credit: yasa | Flickr
Oh yes, sashimi do not discriminate. Instead of raw fish, marry your soy sauce and wasabi with raw slices of pork, chicken, beef and… Wait for it… Horse meat. You might want to down two pints of beer before taking up this challenge.
19. Venture into Aokigahara
Image credit: Patrik Ragnasson | Flickr
The mention of Aokigahara alone would suffice in sending chills down a local’s spine. Outside the fringes of Tokyo at the foot of Mount Fuji is this suicide forest where dejected Japanese enter, get lost and eventually hang themselves. Scattered around the forest you’ll see skeletons, belongings of the dead and their spirits.
20. Beat the High Score at Akihabara’s Iconic Arcades
Image credit: IQRemix via Wikimedia Commons
Test your gaming prowess at one of Tokyo’s legendary arcades in Akihabara. Whether it’s classic claw machines, rhythm games, or cutting-edge VR challenges, see if you can dominate the leaderboard. This challenge isn’t just about fun. It’s about proving you have what it takes to be a true Tokyo gamer.
Also read: 5 Useful Services at Tokyo Station for Convenient Travel
In 2025, Tokyo remains a city of extremes: Where the boundaries of reality and the absurd blur into a playground of exhilarating challenges. From gargantuan food battles and haunted hospital treks to quirky dining experiences and arcade conquests, each of these 20 challenges invites you to embrace the unpredictable spirit of Tokyo. So, if you’re game for an adventure that’s as diverse as it is daring, dive into these experiences and create memories that will last a lifetime. Don’t just visit Tokyo. Live it, challenge it, and let it transform you!
