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Tobi

Obito goes back to Konoha and blends in, passing among the people who live in the village like he still belongs there. This absolutely enrages him. He likes to watch people do all the things Rin won't. It's at least 75% self harm. The remaining 25% is just getting the opportunity to play cruel pranks on random strangers who happen to live in the village. Please get some goddamn help, Obito.

Pein

With regard to the context of how tired and pained he seems in canon, Nagato would benefit most from a staycation in which he decouples himself from the black receivers for a while. Just let him lie down and rest for a while. Get him a snack. Maybe a Fujikaze Yukie marathon? Her movies are very idealistic, that's pretty appealing.

Konan

Don't tell Hidan, but she's going to the Land of Hot Water. For the hot springs! She's going to go to an extremely advanced hot springs/spa type place and plant herself there for at least a week. The Land of Hot Water is perfect because, although it's not the closest beautification/wellness/relaxation retreat featuring hot springs, it has the benefit of now being utterly without a regular shinobi presence — so there's no reason for any wayward spymasters to be taking a work trip out that way. Listen, she lived with Jiraiya for three years. She's kind of got bathhouse trauma.

Zetsu

He rarely gets sent to locations frequented by civilians. His vacation is people-watching at the daimyo's court! It's a little like a butterfly house and a little like a performance. He spends the whole week murmuring quietly to himself (the only company he needs) about the intrigues and intense social politics he's observing.

Sasori

Museums and ancient sites. He has very strong feelings about the decay of these sites and objects over time and their methods of preservation and restoration. Sometimes he's genuinely fascinated to see what people are doing to preserve objects that are, like, 3000 years old and made of wood? There's always more to learn. But sometimes he steps into a municipal museum and he feels bitter and vastly superior. What are they even trying to do here?

Deidara

Okay, Deidara's DREAM vacation is just following Sasori around on HIS vacation and blowing up every site he visits to make a point about the inevitability of entropy. But since he's not actively trying to pick a fight, you'll probably find him squatting in some derelict and abandoned place, planning an enormous performance. It's not always about the size of the explosion — bigger is great, sure, but there are considerations of other qualities. Deidara truly is never happier than when he's plotting something that will go off with a REALLY big bang.

Itachi

He lives a life of excitement, noise and frequent disappointments. For his dream vacation he will have the time and the leisure to take a quiet and sedate little tour of the world-famous teahouses in Tea country. He will sample all of the seasonal wagashi, drink all of the tea, and enjoy the peace, quiet and rest. He will slowly hike between his planned inns during the day. The sun is shining. The birds are singing. It's a nice bit of countryside...

Kisame

He may want to STAY on a boat and have all the privacy of his own little home on the water and get to take it wherever he likes, but Kisame is not a quiet fishing trip guy. He's an Adventure Activities Holiday kind of guy. He will be grudgingly paying the absurd dock fees to leave his little boat somewhere for a few days just so he can trek over a mountain and go white water rafting or some shit.

Kakuzu

Kakuzu... doesn't take vacations. They're expensive and he doesn't really see the point. If he wants to go somewhere, he'll find work there. However, arguably, his life is just one long vacation at this point, since 90% of what he does is travel to exciting new locations to kill people. That aside, he will always make time to visit a rare book fair if one's in town. An easy, lucrative contract, an interesting old book, cheap accommodation and good weather to travel in: that's what he wants.

Hidan

Hidan's idea of a vacation is going to large, crowded cities and gifting them himself as their brand new urban legend/local cryptid/serial killer. His best holiday to date has been one in which his latest string of murders started a riot: 15 dead, 47 wounded, janitor very unhappy. Praise Jashin, he's been trying to top that high ever since.

Orochimaru

Orochimaru will spend the week lying on a pristine, private beach, sunbathing. He will bring one of his beloved little minions as a personal attendant to bring him cocktails on a schedule and to present an easy target for his amusement (it's important that it be someone he knows and likes — he enjoys provoking people he likes, not strangers to whom he's indifferent). He will definitely get bored of tormenting his attendant and lazing about within about three days, pack up and leave, sure. But the R&R portion of the trip is actually very rewarding. Sometimes you just need to sun yourself on a rock for a few days.

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