5 nights in Santorini

Oia is my "favorite thing to see". I know that's not what you meant but I always stay there and love it so much it's difficult for me to leave once I'm settled in. That said, below Oia is Amoudi Bay, worth your time. There are some great tavernas down there right on the water. Sigalas Winery is in Oia, just a short walk from Katikies. There are so many excellent restaurants in all price categories in Oia: Feredini, Papagalos, 1800, Skala, Kastro, Laokasti, Anemomilos, Strogili, Pelekanos, Ochre Wine Bistro, Roka, Kandouni, Petros, just to name a few. Melenio Bakery for amazing desserts!

The island has an excellent bus system and all buses originate in Fira and branch out from there. The bus between Oia and Fira passes close by the hotel. There will be at least one bus each hour. You won't get lost. The island is small. This map will help: http://www.santorini-web.com/map.pdf

When it's time to explore, visit Ancient Thera, Akrotiri (archaeological dig), Museum of Prehistoric Thera and Kamari Beach.

Just wandering and showing up to restaurants was the standard in my experiences in Greece. If you like a place that can't take you, your 5-night stay may mean you have a chance to reserve for tomorrow night. Menus are posted outside, but if it's a pre-printed taverna menu, they don't always have everything. The ready-dishes and fresh fishes are also often on display in a refrigerator case.

Be advised that if you order fresh grilled fish, chicken or beef and it's not specifically priced on the menu it is sold by weight, so be sure to ask the price of the portion before you order it or be prepared for a shock. "Exotic" seafood such as lobster can sell for as much as €75.

I would look into the red beach. It was unique and beautiful, although im not sure what the temperatures will be like in September

sshemali -- the Red beach is CLOSED -- OFF LIMITS -- due to rock falls.

In spite of the obvious dangers, apparently people are still hiking down to Red Beach. If you choose to do so be VERY careful and proceed at your own risk. Personally, I wouldn't do it. I know firsthand just how unstable that rocky cliff above the beach actually is.

The first and foremost reason I would go to Santorini would be to see the two world-class archeological sites at Akrotiri and Thera. While the cliff-side villages and spectacular views would be of interest, the crowds, even in September and higher prices would only encourage me to do a day trip there. If I were to go to Santorini I would base myself in Kamari in the southern part of the island away from the mass crowds and over-toursity main towns. I would take the bus to see the sites at Oia and Fira then rush back to a more laid back area of the island for an evening out.