My traveling companion has a system.
She rents a house, or a flat, or a villa, to serve as base camp for day trips. Thus from Kalo Nero we sortie to Olympia and Pylos; from Nafplio we do Argos, Epidavros, Mycenae, Corinth, and Tiryns; and in Athens we walk from our flat on Vaiku south of the Acropolis to museums, Syntagma, the Plaka, and so on. It's brilliant because we have a familiar place to return to each night, where we can spread out, recharge, and feel at home. It minimizes driving distances, so that the longest of our day trip drives is around 90 minutes.
She did the research, the planning, the booking. We put our heads together to decide on the order of events and the number of days in each location.
On my own I'd have not planned anything. Or reserved anything. I'd have probably changed lodging each night after visiting a new town, and it would probably have been hotels.
I'm good with both strategies. I feel mine is more adventurous, hers more grounded. I like the freedom of mine, to stay in one place if I love it there, to move on out if there's something interesting down the road. But I also like the relaxed feel of having a home. And I love the well-chosen digs she rents.