We are a group of 4 women - 2 friends and 2 daughters, who like to travel. But the men don't. One of us is a single woman, and has gotten the others to travel. We all have different travel styles, some like to see everything, while some want more relaxation. Some are used to scheduled tours, others want the ability to sink in the local culture.
So, while it seems cliche to pick the usuals of Santorini and Mykonos, it fit the mix the best. More time in one place means the ability to see more, and relate to the area more.
The basic plan is one site a day, and then shop or wing it the rest of the time. Schedule the highlights, but leave time for the lowlights.