CPT/Categories/Multi-location question

Hi

I want my directory to offer listings for local businesses, accommodation, restaurants/cafe’s and things to do on the scottish islands.

I want to include all the different islands within an island group, i.e Inner Hebrides would include islands such as Arran, Mull etc.

What do you think would be the best way of doing this? I have the CPT and multi-loations add-on. Ideally, I would like each island page to have their own page with a map and listings on. Not sure whether to use multi location (one for each group of islands i.e. mainland Shetland as the location for Shetland) or whether to use CPT’s. if using CPT’s would it be for the island grou or for the listing name (business etc)?

It may be easier to use Tags. Really not sure of the best way to tackle this as have tried 2 or 3 combinatons and can’t seem to find the right one.

Any help would be much appreciated.