I think it depends on where you live when it comes to expensive holidays, and what sort of accomodation you want. I’m from London and went to the Maldives in oct 2010 2 wks all Inc, £1150. Which was a bargin as previous years I been to Spain spending over £100 day on food and drink etc. I went to the addu atoll on the island of gan which is the most southern chain of islands. The hotel was everything I could have dreamed of, it wasn’t posh or extravergant but who cares when ya in the Maldives. Another great reason to go to the addu atoll is that when the British were there they built bridges and causeways connecting the south and west islands which means u can get on a bike and go and meet the locals, they were so friendly and I recomend the addu atoll to anyone !!!!!
These groups are generally better connected among themselves than with other groups, so you are probably better advised to target them on this basis. As it’s your first time to Greece, you may want the full-on Greek island experience and you could easily fill your five weeks flitting from one island to the other in the Cyclades. You could start in Kea and work your way down to Milos via Kythnos, Serifos and Sifnos then segue to Paros and Naxos. Dip down to Santorini, up to Mykonos and back to Piraeus. The map will also show plenty of other Cyclades islands to pick and choose from such as Ios, Sikinos, Folegandros, Amorgos, Syros, Tinos and Andros – yes! too many choices, but you will find that sticking to one group it will be easier to get between them. Realistically for a period of five weeks you will not want to be doing more than 6-8 islands.