The vague memories I had of Greece are of stray dogs & a desolate Olympic park. Marls & I totally redeemed my perception of Greece with our amazing August 2016 adventure to Mykonos and Santorini.
Hotel Tagoo was perfect for us. Not to be confused with the overly chic Cavo Tagoo hotel nearby, although I was happy to hitch a ride with their airport shuttle.
Our hotel was fine for a few nights and had a nice pool, but I feel like if you're going all the way to Santorini you're gonna wanna view of the crater, volcano island to the west and west means sunset. 😍
Thera is the biggest town on the island so the best base point for going out to eat and drink. Oia and Finikia are smaller, quieter, and filled with honeymooners.
Potential itinerary: MUC to JMK, ferry JMK to Naxos, ferry Naxos to Paros, ferry Paros to Santorini, JTR to MUC.