WORC generally requires that you be off-Island while a Full Work Permit (FWP) or Temporary Work Permit (TWP) grant application is in process. Therefore, do not book your flight to Cayman until your permit has been approved. Furthermore, although the vast majority of applications are approved without issue, there can be no guarantee that any application will be ultimately successful.
However, if you are already on-Island and are switching from one employer to another, you may not need to leave the Island while your new work permit is processing. Having said this, you should make sure that your release letter from your current employer is dated to take effect on the exact date on which you hope to be authorised to commence gainful occupation in the service of your new employer, and ensure that applications are made well in advance. If this is not possible, then you may be required to get a visitor’s stamp in your passport when your current work permit is cancelled to avoid any prospect of you being labelled as an overstayer. Further, particular care should be taken given the potential for any period in the Islands as a tourist visitor to be treated as representing a break in “legal and ordinary” residence – and further, for presence in the Islands as a tourist visitor to itself create a barrier to the grant of a new work permit.