Just got back from 14 days in Greece, 10 of them via sailing boat, and had a wonderful time. I booked a package with G Adventures for sailing from Santorini to Santorini, and added a couple days on the front and back.
I flew to Athens, and then immediately a puddle jumper flight to the island of Santorini. I am glad that I didn't try to make my schedule as tight as possible, since that last flight was delayed 3 hours. High winds tend to mess up flight and ferry schedules, with either large delays or cancellations. So, if you plan something similar, leave some breathing room.
My first day there was a free explore day on the island. Everything is quite beautiful, with the scenic white buildings and blue domes. My hotel was in Oia, a town on the northern point.
I took a bus to the main city in the center, Fira. Fira is where all the cruise ship excursions dock, and it quite busy with tourists. Oia can also be busy with people taking bus day trips there, but Oia picks up in crowds at night since everyone wants to watch the sunset.
While exploring Fira, I found myself slow moving further and further from the city center, and I decided to hike the rest of the way to Oia, normally a 10km hike over a small mountain. Views are amazing, with several churches along the way. I however decided to do it mid-day, when it was about 90*F outside.
Then I wrapped up the day back in Oia.
The next day, I took a cab to the town of Vlichada, on the bottom point of Santorini, to meet up with the group, and start our trip. It ended up being 5 other people and the skipper, so it wasn't a full boat (max 8 guests). We pooled some money together for food supplies, set up our bunks, and departed. It was a 52' sailboat, with was cozy.
Our rough itinerary, based on my geotags of pictures.
First night we stopped at Schoinousea, where we ate at a wonderful small restaurant with heaping portions of food. The next day we continued to Naxos. Naxos isn't as heavily crowded as Santorini or Mikonos, but had plenty to offer. The first night we stopped at the Portara, a massive doorway to a missing temple.
The next day, we rented two cars, and explored the island. I informally named them Team Panda Power and Team Good News, since we had a Fiat Panda and a Dacia Sandero.
The temple of Demeter
We also did some small hiking to the cave that was supposedly the childhood den of Zeus.
After 3 nights at Naxos, the winds were favorable again, and we continued to Despotiko. Everywhere we sailed, the waters were so blue and clear. Temperature wise, it little chilly, but your body got quickly accustomed after jumping in. At Despotiko, we had a BBQ.
The next day, we sailed to Antiparos which was a quaint little island with a scenic town.
After getting lunch and doing some shopping we continued to Paros.
Then we went onward to Mikonos. Cruise ships dock directly here, so there are large numbers of crowds. Buses are often standing room only. However, "Little Venice" has some amazing views, and the beaches on the island are nice. Night life is very happening here, so its easy to find a club somewhere. Just be ready for inflated prices
Then we continued to Ios. It also was very crowded, but with what seemed a slightly younger set of people. Spent most of the day at the beach here, and shopping at night.
Then we made our last leg back to Santorini.
I stayed in Kamari, near the airport and the black sand beaches. Near the airport was correct, as you can see the planes up close as they pass over the beach.
I then took a flight back to Athens for the last day and a half of my trip. The Acropolis, ruins, and museums are amazing, but the rest of the city is meh. There is so much graffiti and trash around, but I guess that happens during economic crisis.