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Cyclades w/kids & my ruins-fanatic DH (itin and accommodation advice)

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2018 is bringing a return to Greece for us and our first taste of the islands (our previous 3 trips were spent on the mainland). As usual, we'll have the boys with us (7 and 5). We will have spent 2 weeks in Italy prior to heading to Greece, so jet lag won't be a factor - just the one hour time diff.

We're flying from Rome to Mykonos and parking there for the first 4 days/5 nights. Plan to see Delos, the archaeology museum in Mykonos, and explore the beaches.

After that... we have 8-9 nights before we head back to Athens where the boys and I will meet up with family friends and head to their family place in Evvia while DH heads to Barcelona for work.

My tentative thought is 4-5 nights on Paros or Naxos, and the final 3-4 nights on Santorini (DH wants to see Akrotiri and Ancient Thira).

Itin/Accommodation Questions:
1. Which island (Paros or Naxos) for a ruins-loving family with kids? The kids genuinely enjoy ruins and jaunts through museums, but they are also kids... playgrounds, pools, beaches, and casual/family-friendly places to eat are important.
2. I'd like to keep our accommodations budget to 200-300E/night and I'd ideally like to have 2 bedrooms wherever we stay. If you've got a rec on whichever island you recommend, please share :).
3. Santorini. Is giving me a headache. Despite hours of research, I'm still at a loss. Santorini is high on DH's list due to the archaeological sights. I'm completely at a loss on what part of the island to choose for accommodations. We appreciate beautiful views, but not enough to spend 900E/night for them to get a 2-bedroom accommodation! Yet a pool or beach access is a priority, as is proximity to a casual and family-friendly restaurant... so which part of the island would you recommend? Driving isn't on our radar as a problem, as we've driven all over mainland Greece and throughout Italy. Correct me if we need to re-think driving for any reason - I'd rather know now!

Many thanks, and any and all advice and insight is greatly, greatly appreciated.


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