I have a ~ 3 week itinerary in May:
3 nights Santorini
11 nights Naxos
3 nights Paros
2 nights Athens
My daughter will be flying into Naxos on the 10th or 11th day and staying for the remainder of our trip, which is why the stay in Paros is disproportionately short.
I’m interested in adding in a different island between Santorini and Naxos and have heard great things about Amorgos, but unfortunately I have pseudo gout in one knee and have to be careful about how much I walk and the type of terrain (too much up/down is not good). I know that Santorini is terrible for this but I will be careful!
Alternatively I am considering adding some day trips to Koufonisia or Mykonos/Delos but am not too excited about being on watercraft too often as I get motion sickness.
Any feedback would be appreciated!