Santorini/Naxos/Athens or Naxos/Santorini/Athens?

I would do 1. Make arrangements ahead of time for taxi to hotel. I went with my family to santorini and Naxos. It was with adult children so we arrived on different flights. Three of our group took 11:00 pm flight to santorini and taxi to hotel.

We had tighter connections to santorini than you are proposing but flying from US overnight not from London.

My brother in law who joined us flew to santorini via Munich so maybe you could find a flight like that. As I recall he had a long layover but decided he preferred that to three flights.

I would do #1, avoids losing precious time staying near airport ... and 3 hours is ample time for the connection, so take the 9:45. In June, after 6 pm, there won't be throngs in the airport, and Unless you are taking Ryan air to Santorini (not my recommend), the domestic flight should still be in same building.

Also I would knock a day or a half-day off Santorini & add it to Naxos. -- spend day 2 & day 3 On Santorini, and on day 4, take the Blue Star @3:15? to Naxos. Santorini is mainly about the Famous Caldera View , NOT beaches, (black volcanic grit) , constant cruise-ship and tour-group mobs you have to strategize to avoid (You have to visit OIA at 8 am or between 4-6 pm to have a chance to walk in the lanes) ... and that always-promoted hike from Oia-Thira is just because there isn't any other hike to speak of. By contrast, Naxos is "a paradise for Hikers" according to the most thorough hiking website http://www.cycladen.be/NaxosEng.htm ... and about 15 miles of golden-sand beaches all in a row, readily available by frequent busses. Plus, the port town is fascinating and NOT clogged with people... and the interior has dramatic landscapes... hillside villages... mountainsides of marble... so much to see/do.

I have to agree with Janet in the day allocation. We had theee nights in santorini and four in Naxos. We would have loved another day in Naxos and we’re fine leaving santorini after three nights (two days). We would have had enough to do had we stayed another night but Naxos has even more to see and less crowds.

My young twenty something sons met us at a beach front restaurant the first night we were in Naxos. They had rented an atv and were exploring the beaches. They came back and told us that Naxos was even better than santorini!!

If you like hiking, we hiked between Oia and Fira the first day we were in santorini. We stayed in Oia so took bus back. Most beautiful hike I have ever done. On Naxos, we climbed to the top of mt Zeus-the highest point in the Cyclades. We could see for miles!

I am going to go with the, fly out same day as arrival in Athens, option as well. While it is a very long haul from the west, sucking it up for another few hours to catch that same day connecting flight will bring you jet lag recovery on an island rather than in Athens. Which is a good thing.

Athens airport is compact and efficient with arrivals on the ground floor and departures one floor up. We normally recommend you need 2 hours to make a connecting flight. For some reason you have ignored the 21:45 (9:45pm ) flight to Santorini. That is three hours so you will have lots of time to make that flight.

I too would recommend you stay three nights in Santorini. While I consider it to be a must see island after three nights the expense and the cruise ship crowds begin to wear on us and we are ready for a much more authentic Greek experience on Naxos.

Adding that day to Naxos will be something you will be happy that you decided to do.
Here is why.

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

Thanks for the advice. I am going to book the 9:45 pm flight to Santorini on the night of our arrival. We are flying on British Airways. Any advice on airlines to use within Greece?

I'm also looking for advice on lodging. We have reservations but all are flexible. Since our trip is short, I'm willing to spend more for a good (convenient, beautiful views) location. Also our rooms have to have two beds.

For our three nights in Santorini, I have a reservation at Scirocco: https://scirocco-santorini.com/
For our four nights in Naxos, I am considering Kalergis Studios: https://studios-kalergis.com/ or Iria Beach Art Hotel: https://www.iriabeach-naxos.com/agia-anna-hotels.html. Both have availability. I want to stay on the beach, but maybe being at Saint George beach near Naxos Town is better?
For our three nights in Athens, I have a reservation at Attalos Hotel: https://www.attaloshotel.com/

One more question - is it worth splitting our time in Naxos between the beach and inland (closer to hiking)?

Be careful with santorini reservation. It looks like they have two complexes and one is on the other side of island. I don’t know exactly where the one in Fira is but probably someone does.

On Naxos, i would absolutely stay in st George beach area. You can easily walk into town. And you are central to everything. We rented a car for several days. We went beach hopping one afternoon and drove around the island the other two (one day we hiked). I would not divide your time to move. It would be much easier to just drive.

There are buses too and our original plan was to take a bus to Plaka beach and then have a car for two days. The man at the desk of the hotel told us we could rent a car for the same price as five us taking a bus round trip. You have two so not the same but I would rent a car in Naxos for a couple of days.

In santorini we did the hike the first day and rented a car the second.

Kalergis studios is on St George beach. Its a great location.

Any thoughts on Santorini lodging? Now I'm thinking Firostefani might be a better location - considering Villa Ilias. https://villailias.gr/

Just noticed the last part of your earlier post. There is no reason to change hotels from St George. All the island transportation uses Naxos town as the base. Its a short walk into town to take the bus to teh mountain villages and hikes.
Naxos Mountains and Villages http://www.flickr.com/photos/stanbr54/sets/72157632110674306/

Villa Ilias is a good choice ... great location, views, has a pool but not as pricey as other pool hotels in the area.

I like your Option 1 better, but I think you should spend just 3 nights on Santorini, 4 nights on Naxos. So much more to do on Naxos.

I agree that Kalergis Studios is a great option for Naxos. If you get a ground floor room, it's just steps from your patio to the sand. We loved that. Also there are sunbeds available from the beach bar adjoining the hotel. When we were there in May, the sunbeds were free for hotel guests. In June, they might require you to make a purchase in order to use the sunbeds. But a small price to pay for the luxury of relaxing by the sea at the end of a busy day, just steps from your room.

Be sure to walk to the far end of St. George's beach (away from the town) to Flisvos Sportscenter. You (and/or your daughter) can rent jet skis, windsurfers and other beach toys there. And just up from the beach is their hotel, with a wonderful "front porch" with comfy couches where you can watch a gorgeous sunset.

Thanks for all the advice. We are set on Kalergis in Naxos. Considering Stefani Suites in Santorini - it's a bit more expensive than the other hotel we were considering (Villa Ilias) but I like the idea of being at a very small place.

Also planning on the 9:45 flight out of Athens.