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Does "I'm going to visit X city, show me a list of interesting place prepare me a schedule to visit them for X days" fit ? Because that's what i'm doing.

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I think in the context of kbelder's original comment, it refers more to people having AI do the actual booking / handling payments, though I'd say you're getting there if you're having it pick out places for you. At that point you're just risking your time, not your wallet, which is easier to believe.

I read "Planning" as it will show me a plan, the decision to follow it or not is mine, not it will handle all the process (booking, purchasing).

And yes there is risk with its scheduling, but it's not like i will do any better, travelling has always come with risk in scheduling

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