Planning next vacation. Suggestions on which shoulder months to travel with warm weather from east coast JFK, Newark,Phila.to Santorini, accommodations,cave villas,hotels, etc. Airlines and hotels. Thanks so much. Rosetta

May is perfect. The weather is mostly stable and warm, prices are low, villages aren't crowded, the locals are friendly instead of burned out and the sea is warm enough for a swim as long as the wind isn't blowing strong. Aegean Airlines has cheap flights from Athens to Santorini: http://www.aegean-air.gr/aegeanen/home/

Village and room prices vary according to your requirements. Beach or Caldera view? Swimming pool? Nightly budget? Access to nightlife or quiet? The more information you volunteer the more precise the recommendations.

Hello, It has been awhile but we now are seriously trying to make plans for 2008. It seems you are the local expert so here are some pressing questions for your help. Same time frame May or Sept. Santorini, pool , caldera with views, quiet side. I like the cave rooms, budget no more that $200 a night, we are hoping to stay 1 -2 weeks and move onto Crete. Thanks Rosetta

If you are willing to splurge it does not get any better than Astra Apartments in Imerovigli. Best views of the caldera, centrally located on the island. We were there in Sept last year. The weather was great, the crowds had thinned and the vistas were to die for.

Hi, Nice guy, Thanks for your rapid reply! Could you tell me what accommodation you booked for comparison? Your evaluation of the room/apartment/suite etc? Thanks so much. We have traveled so much overseas and want new sights/experiences. I found all my help here on Fodors. If any one interested see my screen name and read reviews,especially Positano/ Priano. Thanks again. Rosetta

With the shrinking value of the dollar, $200 narrows the choices considerably for a hotel room with a pool and a caldera view. Check Scirocco Apartments, Villa Ilias, Nikos Villas, Kyma Villas, Studios Margarita, Volcano's Villas and Sunny Villas.

I prefer Oia to Imerovigli. I stayed at the Volcanos Villas for 155 euros per night for double room including breakfast. It has a nice size pool and breathtaking caldera view.

We stayed in one of the Senior Astra Suites. Here's the view on our balcony: http://picasaweb.google.com/pughphot...02461918125506

Just back from Santorini. Stayed at Esperas in Oia. Absolutely fantastic place to stay. Quiet but close to the town and bus route, stunning views, pool, small restaurant/snack bar and really helpful staff.

Hello - my husband and I just returned from Greece last night. We srtayed at Rimida Villas (check the B&B category on tripadvisor) in Oia. We have a great stay - very affordable place. We had an apartment style, traditional cave house. The view of the caldera was truly amazing!! There is a pool a very short walk from the rooms. Short walk into the center of Oia (Closer to town than Kirini and Ikies). We paid 128 Euros / night. My only complaint was that the bed was not very comfortable. The furnishings were appropriate for a traditional villa - not luxury. We loved Oia - in our opinion - the best place to stay on the island. There is a rent a car place, a couple of mini markets close by, oh and a nice wine shop as well!

We flew agean air - pleasant 40 minute flight from Athens.

The weather in October was beautiful!! But, we hear it was unseasonably warm. Wich was perfect for us!! Warm enough to go swimming; The water was refreshing at the end if the season. (I would think it would be very cold at the beginning of the season.)

We went to Santorini in May of 2006 and as mentioned previously the timing was perfect...but the water was cold. We stayed at the Dana Villas and loved it. Here is TripAdvisor's review of the hotel http://tinyurl.com/229o48 . We liked staying here because even though it was in the busier town of Fira it was on the north end and was VERY quiet. Oia, although very nice, is at the north end of the island and is more remote.

The Dana Villas are a cliff style hotel that cascades over the cliff with an wonderful view of the caldera. I believe in May it will be close to your price range.

My husband and I were in Santorini this past July and stayed at Sunny Villas. Rooms were beautiful, view is amazing and the people were terrific. We loved Imerovigli. You are between Fira and Oia so it is quiet but there are still restaurants nearby.
Just an amazing stay. Enjoy

My group was just there in September. We stayed at the The Vedema resort. It is not close to town or anything. But, the service there was unbelievable and the resort was great. We booked the Presidential Villa for the 3 couples and a basic room for me. My 'regular' room was bigger than any of the rooms in the villa. I know this resort will blow your $200/day budget as it is a bit pricey.

I will go back and I will probably stay at the Vedema again.

I'm glad you enjoyed Vedema, it's one of the best hotels on the island. If you plan to stay there again clearly you can afford it. But why bother recommending a hotel where the cheapest room in their time frame is over TWICE what they can afford ("_NO MORE_" than $200)? They want to stay for 1-2 weeks (Vedema=$2800-$5600 minimum!), what should they do, mortgage the farm so they can "blow their budget"?? They asked for recommendations for hotels with a caldera view, and Vedema's location severely limits that. There are no cave rooms at Vedema, something else that was requested.