Yah obviously you should to Shillong first, form there you can take advise of locals of other palace which you have planned . According To my experience you should travel that far most location of your trip first. Then you can visit nearby place afterwards.
Your entry point will have to be shillong. after that you can either plan to fits tgo to cherrapunjee Or jaintia hills. both places have more than one spots to cover. son if you're planning to visit for around a week then you can. comfortably cover Shillong city and the remaining nearby areas!
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