First, our itinerary was aggressive and may not be for everyone - for us it was near perfect. We drove 1,300 miles while on mainland Greece and maybe 200 miles on three islands (Santorini, Naxos, & Zakynthos). I will attempt to break down what worked and what did not in this post.
This is a two part post because it is so lengthy.
Day 1 Windsor to Athens
Day 2 Athens to Santorini
Day 3 Santorini
Day 4 Santorini
Day 5 Santorini to Naxos
Day 6 Naxos
Day 7 Naxos
Day 8 Naxos to Delphi
Day 9 Delphi to Meteora
Day 10 Meteora
Our first day in Greece found us on a layover in the Athens airport before catching a flight to Santorini. We elected to leave the airport and went for lunch away from the airport. There is a service in the airport that will store your luggage and we took advantage of doing this before we headed out. Honestly, we probably did not go far enough on the train (I think the fourth stop) and the options were VERY limited. We made our way back to the airport and caught our flight to Santorini. We rented a car through Santorini-Rent-A-Car (reserved online prior to our trip) and they met us at the airport. We had spent a ton of time traveling but still had enough in us to catch sunset on the caldera. We stayed in Karterados and had a 10-15 minute walk to watch sunset (saved us tons on the lodging cost staying off of the caldera).
Over the next couple days we drove ourselves around the island and took in most of the sites and beaches (we had no GPS but had no problems finding what we were looking for). We checked cruise ship schedules and did our best to be in places that the ships go to on the days that had the lowest number of cruisers (Akotiri, Ancient Thira, etc). As far as beaches, we visited Red Beach, Vlychada Beach and Kamari Beach (Red Beach and Vlychada had their fair share of nude sunbathers with Vlychada having the most). The island is easy to drive around but be advised, driving back from Oia to Thira at night can be sketchy. The roads are not well marked and not lit - just be cautious!
Naxos was our favorite location! Everything there was just perfect in our eyes. Minimal crowd, warm and hospitable people, numerous things to do. We drove into the mountains and had a pleasant day in some very small villages. If you decide to do something similar we recommend two days to drive around the island. There is a lot to see and the distances on the map can be deceiving. We highly recommend Pension Sofi as a place to stay - charming, well run, and a great family to meet.
We arrived back to mainland Greece through the Pireas port. Our rental car had to be picked up at the airport and finding our way there on the local bus was pretty easy. Just go right when you come off the pier (or ask anyone standing around where you catch the bus to the airport). The drive to Delphi took us around 2.5 hours, easy, on modern highways, and I think we spent 8 euros on tolls.
We arrived into Delphi in the evening and went to the archeological site in the morning (get up early and get there when it opens and you may have the place to yourself - we did). Around noon we left Delphi for Meteora, again, modern roads for the most part but some mountain driving if I remember correctly.
We arrived in Meteora early enough to catch sunset. We stayed at Guesthouse Vavitsas (great room with amazing views) and it put us right at the start of the rocks and the monasteries. We went to the monasteries the second day and they got crowded as the day went on. As a guy I had zero problems entering the monasteries in shorts and there were wrap around skirts available for all the girls I traveled with.
Continued in second post