I went on a dream trip to Greece with my husband October 2011. It is the perfect time to go, weather was not too hot with cool evenings, and it's not crowded :) But if you’re going to hit the islands be sure to go within the first two weeks of October as a lot of restaurants and businesses close for the winter starting third week of October.

Esperas Traditional houses was the perfect place for our Santorini experience. We rented a car at the airport and made our way to Oia (the most beautiful town in Santorini) known for its amazing sunsets. It is a charming little town where cars are only allowed on the outskirts so its walking, walking, walking to get around. Bring comfortable shoes.

The location of this hotel is absolutely perfect. We sat out on our balcony at sunset time and saw the crowd of people up on the left cliff side that had come to view the sunset...meanwhile wine glass in hand, backgammon board on the table we were relaxing and taking in the magnificent sunset.

The staff is very friendly and extremely helpful, going above and beyond. We had the house located ‘lowest’ down on the cliff, so we had complete, romantic privacy- heads up tough- it is a hike to get up to the breakfast/front desk area which then leads into town. However there is a secret shortcut (which front desk will tell you about) down to Amoudi (the fishing town below Oia). So that walk was shorter which was helpful as we walked up and down about 4 times to get to the yummy fresh fish restaurants for lunch.

IMPORTANT: We had a storm that rolled in on our second night there and it rained all night. It was actually quite romantic, however I woke up at about 2am to a trickling sound, water was coming in by each other the three windows and below the door. It wouldn’t have mattered much, as it was easily wiped up the next morning but I had placed my bag in the little area right under the window my bag was soaking wet. I was able to hang dry my clothes the next day, thankfully we had another day there, and thankfully I didn’t have any electronics laying there either. Speaking to some of the other guests the next morning I realized that it wasn’t just our room. So personally I think the hotel should let you know that this can occur and not to place any belongings below the windows or near the door.

Just quickly a few other notes:
We did a swimming tour into the center of the caldera to swim in the sulfur waters on Nea Kameni (the island still remaining in the center of what used to be the volcano) we took a private tour with a captain named GEORGE LAMPROS who owns his own “little pirate ship”. If you don’t want to do a lengthy half day tour with 30 other people and food and wine on board. Just book George we did a two hour tour which ended up cheaper than the other tours crowded with passengers and we had the boat all to ourselves. George is very friendly, knowledgeable and fun.

Some great food:
TIS PANDORAS It is in Amoudi (the town below Oia) again heads up here there are many steps down this cliff. There are donkeys but after watching and hearing tourists get their legs scratched on the walls (the donkeys always walk on the most outer part of a turn since the stairs are widest there) I don’t know that I’d recommend that. Get the fried Snapper, the “little fry fish” and the dolmades (stuffed vine leaves) absolutely amazing
AMBROISA-NECTAR: Not too far of a walk from Esperas and such good food. The baked feta appetizer is so yummy.
Can’t remember the other restaurants but the hotel staff made the recommendations and they did not disappoint. They were honest about which places were worth going to, which were overpriced and which had the fresh catch of the day. I would trust their recommendations.
When returning to Santorini, as I hope to do some day, I will be staying at Esperas Traditional Houses. I highly recommend it!