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Best Greek island/s to visit in 4-5 days - need help deciding!

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Hi, I have spent the last couple of days going though the forums on this topic & there are many, but I am still confused! I will be joining my 21 year old daughter in Thessoloniki after her Study Abroad session ends on July 22nd. I will probably be getting there on the 23rd & can either stay there one or 2 nights. That leaves us 4 or 5 days for the Greek islands, from July 24/24 - July 29th.
I had originally decided on Santorini since that was the one I had heard of the most. Since I am trying to do this on a budger, I had even tentatively decided on where we were staying - 2 nights at Hotel Sofia in Firostefani & 2 nights at the Lauda Hotel in Ola..(Any opinions?) We are late starters but tend to stay out later at night, thats why I was splitting the time in Santorini in case Ola is too quiet. We enjoy views but DD also enjoys the beach which is why I am wondering if only Santorini is the right choice. Though maybe she gets enough time at the beach in the month she will be at Thessoloniki!
Should we think about visiting 2 islands in 4-5 days? Flying between islands does add up, not sure if the ferries are much cheaper. Also, if we do 2 or 3 nights in Santorini, which other island should we add? It should be one that is convenient to get to from Santorini & that has different attractions, probably one with great beaches. We will be returning to London so also one that has a good flight connections to London (not Gatwick) or from Thessoloniki if we do the other island first. We have not had a problem moving hotels etc in a couple of days in the past.
Are all the islands fairly safe for two women to be out at night etc? Is any better/worse?
If we do split our time between islands, which town/hotels in Santorini should we stay in? Also, how should we split the 5 days?
Do the ferries need to be booked in advance?
Any help would be much appreciated. Thanks, I know I can always count on Fodorites!

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