My friend Rheanna and I spent two days on Santorini. We were skeptical about our visit because of the high profile of the island. We stayed in Fira because it is so centrally located and we had limited time on the island. It’s definitely not a beautiful town, but it worked for our needs. We stayed at the Fira Backpacker’s Place. We booked a private room through Airbnb.com. For $71USD a night, it is one of cheapest places to stay on the island.
The town of Oia is worth visiting and is the quintessential Greek town. If you are going for the day, I highly recommend going early in the morning before it gets too busy. Keep in mind it is incredibly expensive compared to other Greek islands and towns. The rest of the island has a lot to offer so don’t spend all your time and money there. We visited a few of the wineries (check opening hours if you’re there outside of the tourist season), hiking trails, and beaches. The bus system was very helpful, somewhat easy to use (with little help from the drivers), and was the only cheap thing on the island.
We used the buses to get to some of the wineries on the island as well. We took the bus towards the airport/Kamari. On the route back, it stops near the town of Exo Gonia. There are a handful of wineries that are walking distance from each other. We visited Art Space Winery and Estate Argyros as well as Artemis Karamolegos, which also has a restaurant. Here is a link that helped us find all of the wineries.