Which islands?

yes, those are good islands to check out, look for hotels.

Sounds like a great trip. How many days will you have?

Experienced travellers to Greece recommend you get out to your first Island on day of arrival. Keep Athens for the end of the trip so you are on the mainland the night before your return flight.

Both Naxos and Paros have what you are looking for with an authentic Greek experience with good beaches and lots to see and do. They are certainly low key when compared with Santorini and Mykonos but by after Mid June both will be busy as it is close to high season .
Both need a week to really explore. Naxos is even better with 10 days as there is so much to see and do there. The main town has an active waterfront promenade with an old town topped by a Venetian era Kastro, Naxos is blessed with mountain villages, hikes and beaches. Your kids will not be bored on these islands.

While Milos is also a good choice, Paros and Naxos are an hour ferry hop from each other while Milos is as I recall about 5 hours by ferry as its a bit out of the main Cyclades island chain. Every ferry hop you take will eat up half a day. Naxos or Paros to Milos will get you in by late afternoon so that hop eats up a day of your holiday

The only issue you have to take into account is when does your transatlantic flight arrive in Athens. If it is early evening the flights to Naxos and Paros have finished for the day so you will have to spend the night in Athens and fly the next day.

I can recommend Boutique Hotel Glaros at St George beach on Naxos. It was named on of the top 10 Boutique hotels in Greece by the Times of London a few years ago. While there is a one story taverna in front of Glaros all the rooms have sea views. The breakfast is pure Luxury and the menu changes daily.

We just spent 4 nights there in early June. I do not have my photos ready yet but when I have them I will post here so you can see the hotel.
Here are some images of Naxos
Back to Naxos 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299940917

Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481
St George Beach https://www.flickr.com/photos/stanbr54/albums/72177720299943096

St George beach hotels. https://www.flickr.com/photos/stanbr54/albums/72157632162394787
Images of Glaros are in this album but do not reflect our trip this June.

Thank you so much for all of this info, it’s fantastic and I love seeing the pictures! I think we will have 10 days total. You convinced me to drop Milos from the itinerary. I will look into that hotel! Thanks again!

What activities do you enjoy? If surfing is one, then choose Paros. I have not made it to Naxos and Milos and therefore cannot comment on these.

Also, do NOT bother with Ios, which is a get-drunk-with-strangers-till-dawn type place.

Thank you! We love the water but not surfing. We love sailing, swimming, exploring, SUP and are foodies. We tend to be pretty mellow and despise a party scene.

Here is the Boutique hotel Glaros photos.
https://www.flickr.com/photos/stanbr54/albums/72177720300366468

Congratulations in advance!
What an exciting trip for you and your family!
Asking for good choices is a good question however asking for good islands is like as a person about favorite children!
Are you primarily there for the beach or interested in historical or archeological sites? Other interests?
Also consider how long it takes to get to each island and how you will get there (air plane is quickest but you could take a ferry).

I do think Athens and the surroundings are worth several days (Parthenon, Agora, Archeological museum, etc.) I don’t think you should skip Athens altogether unless your family is not interested in these kinds of activities.

Not sure if one is offered in Athens but I have done Segway tours with my teens/young adult children and they loved it! My advise is to do some things that your kids are interested in. You know your family the best!

My kids have also enjoyed local boat excursions and walking tours in different other European countries we have visited, as well as opportunities to just be by themselves doing whatever they want to do, while me and my husband had “adult time.”

I hope this helps. 😊

Thank you! We are interested in beautiful, calm beaches and water activities mostly; adults are highly interested in history but one of my kids not so much so we need to balance that. Segue tour is a great idea! We also just want to wander around small villages. Provably do some small boating excursions. So mostly nature and authentic Greek in as calm an area (tourist and crowd wise) as possible. We do like really like, luxe hotels (not posh in decor, just high end service and facilities wise). Thanks again!

Thank you everybody for your feedback. We decided on 6 nights in Paros and 3 nights in Athens!

Naxos and Paros are good choices. With these you have the benefit of being able to take the excursion boat to the world heritage island of Delos, which allows you a couple of hours in Mykonos Town Going to Delos from Paros takes less time at sea than if you were to leave from Naxos. There is also a local shuttle ferry from Paros to Antiparos that leaves the west side of the island from the port of Pounta, that only takes about 10 minutes to make the crossing. You can even take your rental car if you have one. Antiparos is a lovely little island and up in the hills there is a fascinating cavern you can safely explore.

Thank you so much! These are all great suggestions. I do think we will rent a car!

Google “A lazy day with Captain Ben” — a boat trip around Antiparos that I think you will all enjoy. He stops at Pounda on Paros to pick up/deliver passengers. Food, music, swimming from the boat.

That sounds like the perfect activity!!! We are boat people so I will definitely do this. Thank you!