winging it

We are planning to go to the South Pacific for about 6 months starting this November or December. Cook Islands are on the list. Is it possible to just wing it with hotels and air flights? We prefer higher end accommodations. Is that feasible? I hate to be on a schedule.

The only things you absolutely must book in advance are the flights out of the next country you are about to enter, as having an onward ticket is a requirement to enter every country in the region.
If you want to keep things flexible, book ones where you can change the date later.

The two peak times for people to travel in the pacific are Christmas and winter. From November till March most places are fairly quiet and some places aren't open or running full services - especially in less touristic or more remote areas. Christmas is the time that family members from overseas return home. Often they will be staying with family but many will be in Hotels, guest houses,motels etc
Rarotonga not be too busy in November ( and being further south than some other places, will be cooler than some) so could be a good starting point - although the only places you could fly to from there ( I think) are Tahiti, NZ and Hawaii.
Fiji is a good hub with more flight options and tourism is well established - but you can still get off the tourist trail.
You can fly to Tonga and Samoa from there ( and more)
Remember that after Xmas through till about March is cyclone season, Tonga and Fiji have been in the path recently but any of the islands could be affected.
May till September is peak season in the pacific and I have travelled around Fiji and Samoa during this time just winging it with no problem finding reasonable accommodation - sometimes going back to a place that looked good but was booked out at the time and sometimes making do with second best but always found something. In July( peak school holidays winter holiday time) in Rarotonga I booked most of my accommodation just in case and found there were still some vacancies and I probably could have got by. You are officially supposed to have booked accommodation when you land so it might pay to book the first few days anyway.

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