In Santorini we stayed in the capital city, Fira. On this island I would definitely recommend staying in a more developed city because there’s more things to do and everything is close which is much more convenient. The other main city is Oia, which we visited one of the days. The hotel we stayed at is called Kastro Suites. It’s quite small with less than 10 rooms but I really loved how quiet and private it felt and every room has an amazing caldera view. This was the most important to me when looking for a room. I would suggest looking for a hotel that provides breakfast. It was very convenient not to have to look for breakfast every day but just be able to eat quickly and start exploring. Be prepared for a lot of walking and stairs all over the island! Even within the city we stayed at, there was stairs between the shops and the ground is all uneven stone. To get up to the hotels you have to drag your suitcase up a large hill. Most hotels can help carry the luggage so I would call ahead to check.  I packed a few pairs of heels and ended up wearing sandals the whole time! For exploring the island you can either get a rental car or lots of people get ATV’s. We decided to get a rental car because they picked us up from the airport, there was A/C and they drove us to the ferry port after our stay. We used Spiridakos for car rental and we didn’t have to pay for parking anywhere. The fun in Santorini is going around and seeing everything from one end of the island to the other. It’s quite small and you can drive the whole thing in about an hour. If we had more time I would have done a sailing cruise but I feel like I got to see everything I wanted to.