It seems like Fira is more in the thick of things---I would assume the views are beautiful there as well. Any suggestions for a hotel that has caldera views for about $250-300 per night?

I've only been to Fira once but we stayed at Dana Villas and really liked it. There are a lot of steps at this hotel...200 or so between the top rooms and the pool/restaurant at the bottom. The view of the caldera is incredible. Check it out at TripAdvisor http://tinyurl.com/23s29w

If you have the time, see both of
them. If not, then Fira would
be the best. They have some wonderful
ruins, there. Don't miss them.

You might not appreciate being "in the thick of things" if you are planning to be in Fira in July or August. Between the thousands of cruise ship passengers and the "regular" visitors to Santorini, Fira is an absolute madhouse during this time. If you stay in the nearby villages of Firostefani or Imerovigli you can still have the spectacular caldera views and be a short walk away from everything Fira has to offer.

Check the Villa Ilias, Vinsanto Villas, Veranda View, Nomikos Villas, Dana Villas, Tzekos Villas, Scirocco Apartments, Hotel Kavalari, Enigma Apartments, Blue Dolphins Apartments, Spiliotica, Theoxenia Hotel, Anastasis Apartments and the Santorini Princess.

Oia is the most beautiful village on the island. There are lots of excellent restaurants, shops and galleries there. The nightlife is limited to a few quiet bars and one venue for traditional Greek music and dance, Santorini Mou.

Check Volcano's Villas, La Perla Villas, Delfini Hotel, Strogili Houses, Oia Mare, Nostos Apartments, Aspaki Suites, Chelidonia Villas, Atrina Houses and Ikies Houses.

Personally, having stayed at Oia and visited Fira by local bus, I would definitely recommend Oia. Fira is very busy and has heaps of tourists plodding around the shops and streets every day having been released off the multiple cruise ships which visit. Oia is much quieter and really beautiful with spectacular views, good restaurants and accommodation. It is the best place to watch the sunset from the church (you will recognise it from the many postcards which depict the scene). Can't remember the name but we had a very small apartment on top of the cliffs overlooking the caldera which had a balcony (tiny) but an amazing view. We could see all the cruise ships entering and leaving Fira. This was about 8 years ago so can't really help with prices.

How difficult is it to get from Oia to Fira--I hear it is a long and somewhat treacherous walk??? How far by taxi or bus?

Stay in Oia. Fira is a zoo.

Stay in Oia, definitely. Quiet, quaint, it has everything that Fira has, but less - less noise, less crowds, less stress. Watching the sunset is a nightly ritual and spiritual event for tourists and residents alike. It is an easy bus trip to Fira from Oia. Your hotel will direct you to the square where you catch it. Oia is small enough to have only 1 bus stop, and it's at the end of the line so you can only go one way. (I think I'm remembering that right.)I also think it costs 1 euro. The bus can also take you to other parts of the island - beaches, ruins. If you do stay in Oia, try to stay near the center. There are some beautiful places to stay a couple of miles from the center, but if you can be right in the middle of things, you can walk to everything. Get your legs in shape for the hills!

I will be going in late September, so maybe Fira would not be as crowded then? I am afraid of Oia because it seems "remote" from the rest of the island, and I would assume that Fira also has beautiful views and we can visit Oia?

There are frequent buses between Fira and Oia between 7 AM and 10:30 PM. The bus will stop wherever you are to pick you up, all you have to do is flag it down. The cost is 1.2 Euro. Get on board and someone will come to you to collect your money.

The bus takes about 20 minutes to reach Oia from Fira.

Oia may seem "remote" but there are plenty of excellent restaurants, shops and galleries there to keep you occupied as well as a few mellow bars and one venue for traditional Greek music and dance, Santorini Mou.

Fira will still be crowded in September, have no doubt.

Thanks so much for your advice. You ahve talked me into Oia!!! Esepcially since the bus ride is only 20 minutes away if we want another "scene."