WARNING: Do not go to Santorini unless it's July, August, or September if you want guaranteed, stable nice weather. The first two days were very cold and very windy. While the island is still a beauty, this substantially detracted from our experience. Now I understand why many locals leave the island in winter.
A friendly local was waiting at the airport with our rental car (cheapest option at santorinicarrental.com, 75 euro for 3 days). Apart from the fact that the tank was empty, we had zero problems with the car rental. Having read the horror stories here, I was careful to take pictures while picking it up. It turned out that renting a car was the right thing to do: We drove over 200 km in three days, exploring every corner of the island.
Day 1: Drove to the hotel (not easy to find). I have only praise for Remezzo Villas. The place is gorgeous and the service outstanding. Had dinner at Taverna Imerovigli (OK).
Day 2: Our favorite breakfast: visit the village bakery, drive to Firostefani, have breakfast on the bench next to the main square with caldera view. Explored Fira. Drove to Santo winery (great view). Continued to Perissa (semi-deserted). Drove all the way along the coast. Stopped for lunch at a small harbor near red beach. Had pretty good lunch at restaurant overseeing the harbor (I think it was Dimitri). Very good Santorini salad and octopus. After lunch we stopped in Pyrgos, then drove to Red Beach (beautiful). Finally drove all the way down to the lighthouse. Stopped at Boutari winery on the way back. Had dinner in Fira at Nikolas (mediocre).
Day 3: Drove up the island peak. Not much to see there, the monastery was closed. There is a small chapel, which was closed as well. Drove past Kamari to ancient Thera. Very nice, but the wind almost blew us away. Lunch at Galini (good octopus and sardines). Stopped in Fira with the intention to see the museum, but it was already closed (3 PM!). Drove to Oia for the sunset. Lots of people gathered for a regular sunset (duh!). Had the best meal on the island at Roka.
Day 4: Saw the museum in Fira (small but nice), then drove north to Domaine Sigalas winery. Very nice winery, with excellent Vin Santo and very good Niambelo red, a favorite of mine (8.20 euro per bottle at the winery). Lunch in Amoudi bay. The bay is gorgeous. The lunch at Katina was mediocre (I missed Tis Pandoras, the first restaurant coming in). Back to Fira for last minute souvenir shopping and to pick up some gyros at Luckys for our evening flight to Athens.
We enjoyed our three busy days in Santorini. But why is it that fish costs so much? 40-50 euro (except for calamari and octopus), and not at fancy places. I can't believe locals pay that much.