First trip to Greece June 2020 with Teens

We brought our teens to Greece several years ago. We took them to Naxos as it was( and still is ) our favorite island. We spent a weeks there. They loved it. They felt safe to wander around Naxos town their own. It is still a safe place. We stayed at St George beach so it was an easy 10 minute walk into town. They loved the drive up into the interior, small mountain villages, switchback roads and a smattering of antiquities along with amazing beaches.
We then ferried to Santorini for three nights and flew back to Athens for the last few nights.

Later on they told us that they thought Santorini was amazing but they would have been happy with two days there and an additional day in Naxos. They still talk about that trip. You will be making lifetime memories with your kids on this trip.

Post script. We took our now married son and his wife back to Greece. My plan was to spend 10 days in Naxos and the last three in Athens. My son insisted that his wife had to experience Santorini. So we flew there, spent three nights then ferried to Naxos for 7 nights then flew to Athens for the last three. It is still a wonderful memorable island trip for a family.
Here is what we saw.
Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/

Trip around Naxos

http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Athens http://www.flickr.com/photos/stanbr54/sets/72157632121475515/

Thank you. Your photos are beautiful!

How does this sound?:
Fly out of Chicago
Day 1 Fly to Santorini
Days 2-3 explore Santorini
Day 4 Ferry to Naxos
Days 5-8 explore Naxos
Day 9 Ferry to Athens
Days 10-12 explore Athens
Day 13 Fly home

We'd like to get flights book in the next few days.

Your updated itinerary looks good to me. We loved both Santorini and Naxos! I would suggest that you fly from Naxos to Athens, rather than take the ferry. It's a 45 minute flight on Aegean Airlines. The Naxos Airport is extremely small, so no need to get there hours ahead of time. Enjoy your trip!

Do you have recommendations on where to stay?
In Naxos, we would like to be on the beach. A kitchenette or breakfast would be nice.
In Athens, we would like to be able to walk to our sites.
I'm open to suggestions in Santorini.
Thanks again!

We were extremely pleased with all of our accommodations:
Naxos: Hotel Grotta (small, family run with a huge delicious breakfast; sunset views from our sea view balcony; they also have a rooftop garden; not on the beach, but an easy walk to town; excellent price point; )
Santorini: Lithies Traditional Homes in Firostefani is heaven on earth! (on the caldera; five star service and advice from Maria who makes your stay perfect; breakfast included as well as afternoon wine and snacks; loved every second of our stay and hated to leave; it books up early; excellent value in Santorini; there are different "homes" to choose from)
Athens: InnAthens (near Syntagma Square; easy walking distance to everything; breakfast buffet as well as made to order items; modern rooms that are immaculately clean; friendly and professional staff)

In Naxos we booked a private half day tour with Naxos Discovery Tours that was wonderful! Nicolas is a wealth of information and you will see things that are not on a larger bus tour. IMO it was very reasonable priced and worth every cent.

Hotel Grotta is not near a place to swim (the "grotta" swim area, from steps decending off the causeway, is not a beach, and few people swim there, near the ferries. One can stand on the main road near the hotel and catch a bus to outer beaches. However, for teens, in June we always recommend St. George Beach (Ag Giorgios) -- for a number of reasons:
• Hotel Grotta doesn't have accommodations for parents & teens to stay together. St. George has a number of family-run pensions (12 - 25 units) that work well for these 4; a bedroom, pllus a large main room with 2 daybeds, kitchenette nook, table & chairs & large balcony.

• It's ON a beach yet an easy 10-minute stroll to the port town attractions of cafes, shops museums, theKastro, etc. Thus a family doesn't need a car except for driving around the island to explore.
• This family has older teens who want to be independent & not stuck with parents fulltime, and Naxos is a great place where teens can safely congregate with other teens, on the beach & at town gathering-spots like Waffle House -- just have them take phones & check in periodically. Grotta is not a teen-type place.
• Ag Giorgios is also good for active sports -- theFlisvos Sports club rents & coaches for kayaking, windsurfing & other water activities.
• From Grotta, you must always leave to find dinner... if you're feeling lazy at sundown, Ag. G has several tavernas right on the beach, where your chair-legs sink in the sand and you watch the stars come out.

I would second the suggestion of flying back to Athens from Naxos. Both Sky express and Aegean/Olympic fly this route. Prices will only go up so now is a good time to book this flight as well. 45 minutes to Athens versus 5 hours by ferry. I will always fly in order to get going sooner in my next location.

We normally recommend St George beach because its part f Naxos town. Its also the transportation hub which is important for you when you want to get up into the mountains for hiking.
However if you are really into beaches you could consider Plaka beach. Its about 3KM long and has a string of Hotels and tavernas for accommodation and dining. Its well serviced by local bus so you can get back to Naxos town easily. Here are some images of the various beaches.
St George Beach Hotels Naxos http://www.flickr.com/photos/stanbr54/sets/72157632162394787/

St George Beach Naxos http://www.flickr.com/photos/stanbr54/sets/72157632113170279/

Plaka beach tavernas hotels https://www.flickr.com/photos/stanbr54/sets/72157655106193251

Aggia Anna and Ag Prokopious beach areas
https://www.flickr.com/photos/stanbr54/albums/72157656297072028