Wacky Weekend and the Itch to Go Somewhere Weird This Saturday

I’ve been watching two grown men spend $15,000 renting a Japanese castle and dress up as samurai for a full historical experience. And somehow, it’s given me the itch to grab a friend and go somewhere weird this weekend.

The show is called Wacky Weekend. It’s split across two channels — episodes planned by Chris live on Abroad in Japan, and episodes planned by Connor live on CDawgVA. The format is simple: they take turns planning surprise weekend trips for each other somewhere in Japan. The unspoken rule is that it has to be weird, wacky, or both — and ideally, the other person suffers at least a little.

How I found it

The Okinawa island episode. They were hopping between remote islands, eating things I couldn’t name, doing things no sensible travel guide would recommend. I was hooked immediately.

What got me wasn’t the production quality — though it’s genuinely cinematic for YouTube, shot and edited like mini documentaries rather than vlogs. It was the feeling that I was watching a real side of Japan. Not curated. Not sanitised for tourists. Just two people reacting to genuinely strange situations with their full, unfiltered personalities.

Both are British — Chris is English, Connor is Welsh — which adds its own layer of comedy. Two people from a famously reserved island nation, dropped into one of the most culturally specific countries on earth, reacting to everything with either deadpan horror or unhinged enthusiasm. Chris is the dry, sarcastic one — British restraint weaponised into a comedic instrument. Connor is pure chaos energy. Together they’re an excellent straight-man-and-disaster-magnet duo. The comedy comes naturally from the dynamic, not from a script.

The castle episode

My favourite episode is probably the one where they rented Ozu Castle. An actual historical Japanese castle. They got the full samurai experience — armour, ceremony, the works. It cost them $15,000.

I will never do that. That’s not even a realistic fantasy for me.

But watching them do it is strangely satisfying. There’s something fun about seeing privileged people react to extreme versions of things with complete sincerity. They weren’t performing amazement — they were genuinely overwhelmed by it, and that came through.

What it’s actually about

The show looks like travel content on the surface but it’s really about the format — two people trying to out-weird each other. They take turns being the planner and the victim. The planner’s job is to pick something unusual enough that the other person has no idea what’s coming. The victim’s job is to react honestly.

That structure makes it rewatchable. It’s not about Japan specifically, even though Japan is a great setting for it because it has so many genuinely strange corners — remote towns buried in snow, isolated inns with no electricity, tiny islands nobody flies to. The kind of places that don’t end up in highlight reels.

What it made me feel

I want to visit Japan. That’s not new — I’ve wanted to for a long time.

But Wacky Weekend changed the shape of that want. I don’t want the Tokyo tower photo or the Kyoto temple morning.

More immediately though — it made me think about where I live.

India is not the easiest place to travel spontaneously. The budget is different. The logistics are messier. It’s not built for that particular kind of casual, low-stakes adventure the way Japan seems to be. But the spirit of it — picking somewhere odd, dragging a friend along, seeing what happens — that’s not geography-dependent.

There’s probably somewhere within a few hours of me that I’ve never thought to go. A town with a weird history. A place that’s inconvenient enough that nobody bothers. Something that would make a good story later.

Wacky Weekend is good post-lunch couch content — calm, funny, easy to watch. But it’s also quietly persuasive. It makes you want to leave the couch eventually and go do your own version of it.

I’m thinking about it.