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Greece- why is this so difficult?

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With two BIG birthdays coming up in the autumn my husband and I want to take our family away.
It looks as if it will be Greece and sometime after the `12th June.
Without going into the reasoning these are the things that I think will work
1. We like small local places (hotels I suppose) from which we can walk to restaurants at night. Not looking for five star but it would help or in fact we DO need a pool. Recently we have returned to the Hotel Anixis in Naxos Town which would be ideal if it had a pool.
Needs to be quiet at night

2. Not ruling out a villa ( which is probably more likely to have a pool) but that is less likely to be within walking distance of a town as per 1. above. If it was to be a villa we'd probably want two because of a tot who doesn't sleep the same hours as us.

3. As we would be flying from different places we are looking at somewhere with direct flights from the UK.

4. Duration of 7-10 days

We will be six adults and one grandaughter who will be three. We have seen many Greek islands and that should make it easier but it doesn't. Current fave is Naxos but we've been there 4 times in the last five years and so my husband and myself have really seen a lot of it. However I always remember thinking that Skopelos was really the best destination with a little one. On the other hand its 34 years since we were in Corfu and I loved that. To be fair I should say that probably the only island I've visited which I wouldn't consider is Alonissos and that is because it was all closed- it was Sunday!

Any ideas please?

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