Ah Santorini...one of my favourite places in the world.
We stayed in Firostefani at Tsitouras Collection, which was beyond fabulous. It's a former private residence - only 5 rooms. The best room by far is the Nureyev, with it's own private terrace, then Winds and Portraits which are also very nice but no comparison. The pool is brand new and stunning.
http://www.tsitouras.com/
The owner Eleni Tsitoura is AMAZING!!! Tell her I referred you. The service is like nothing you've ever experienced. It's like having your own private hotel but with round the clock staff who are incredible yet unobtrusive.
The property is located right on the edge of the caldera, up very high. It can be chilly at night so take sweaters. It's also super casual, like SBH. It's very private too yet it's a 5-7 minute walk from where the town of Fira starts, which is the very touristy area with all the shops and restos. We walked into Fira every day/night. The hotel is also walkable to lots of very good restaurants. We rented a car so we could drive around and go to the beaches. Eleni's husband runs the car rental company and he was lovely. He brings the car right to the hotel.
You must drive to Oia, the most westerly tip of the island known for the most beautiful sunsets in the world, though the sunsets from our hotel balcony were identical and totally peaceful. Literally hundreds of loud, belching tour buses arrive in Oia very afternoon filled with German, Dutch and Brits all there to gawk and take pictures. Go to Oia for lunch and to walk around and then head back to Tsitouras for a private sunset viewing from the chairs at the top of the property - the most stunning, unobstructed view of the same sunset but without the crowds.
Restaurants
Lunch:
Lucky's Souvlaki - a whole in the wall right on the main road in Fira heading towards Firostefani. Counter seating only. The best gyros I've EVER had and owner Lucky is a hoot. Super cheap and just fun.
Dmitris - Ammoudi - For me the best meal of the trip. Ammoudi is past Oia at the far west end of the island. It's a wild drive (not wilder than SBH) through beautiful terrain. Right along the water are a handful of seaside restaurants. Walk right to the very, very end and that's Dmitris. Owned by Dmitris and his Canadian wife, Dawn, she'll take care of you. The fish is caught right there. Don't miss the fish!
Perivolos Beach is a black beach at the far eastern end of the island. It's filled with beach clubs which are very fun. By far the nicest beach club is called JoJos. You can rent chairs and hang all day listening to great music and eating and drinking. The beach boys serve you at your chairs. Very chill. Best Santorini salad. Big and varied menu. Lots of other restos along the beach too.
Dinner:
Aktaion - A stone's throw from the hotel is a teensy, charming, very traditional family taverna in Firostefani. Nothing fancy, but nice home cooked Greek food.
Il Cantuccio - also a stone's throw from the hotel - very good Italian fare - cheap - pizza, pasta.
Archipelagos - Fira - carved into the cliff of the caldera with a stunning view if you go before dark. Big and varied Greek menu. More gourmand, superb food. The feta, artichokes were to die for as was the fish. Beautiful and special. Doesn't break the bank.
Vanilia - my FAVORITE resto by far for dinner. We went 3 times! Two minute walk from the hotel in Firostefani. OMG! Gorgeous, outdoor, romantic, vine covered, charming Greek resto. But the FOOD!!! Ask for the owner Dmitris. Tell him Gayle from Toronto (Jennifer's friend) sent you. He's fabulous. And his two waiters - Niko and Kosta - fabulous!!! Do not miss this resto! Reservation a must.
Have fun. Book soon.