I'll be heading to the Greek islands later this month and will be spending the entirety of my time in the Cyclades. I have the first half of my trip planned out and would love any insights on must see's / do's / and other recommendations. I'm a 34 year old male and will be travelling with two females of the same age range. We like to lead the life of "work hard play harder" and are eager to take in the scenic beauty of Cyclades as well as a bit of partying and nightlife. We're not people that require anything fancy or over the top, just a bed to sleep in and a roof over our heads, experiences matter more than anything else!
I've got the first half of our itinerary planned out and would love feedback or insight onto the latter half. The caveat is we need to be on Paros by May 25th for one week. Afterwards, we can island hop for another two weeks up to June 12.

Our confirmed itinerary:

May 13: Santorini
May 14: Santorini
May 15: Santorini
May 16: Santorini
May 17: Ios
May 18: Ios
May 19: Ios

Our hypothetical itinerary post May 19

May 20: One more day Ios / Milos
May 21: Milos
May 22: Milos
May 23: Naxos
May 24: Naxos
May 25-June 1: Paros
June 2-12: ???