Using Crete & Naxos as a home base for 2 weeks

Are you asking if Naxos is a good choice? Are you asking if you should go to Santorini at all? Are you asking if these three are good choices (or is Crete a given)? And then lastly, you are asking what order to do them.

Im only responding because no one has so far and I am doing a similar trip and have kids ;p (same islands you mention). I think your plan sounds good. Crete has something for everyone and can easily fill that week and offer the kids lots to do. I think going there first is the right order. And then I also think Naxos is a really good choice. From all my research, it also offers a lot for different ages, and like you said, the surrounding islands can offer something different as needed. The ferry we are taking from Santorini to Naxos is 90 minutes OW. So that would be a long day (3 hours travel). When I was making my plans I was debating going to Santorini and everyone here said its a bucket-list type of place. We'll see. I know people go with kids and find plenty to do, so the question is perhaps whether you 'should' stay a night or two, maybe en route to Naxos? (We're doing Crete- 10 days/nights, Sant. 2 ½ days/3 nights, Naxos 5 nights/4 days)

Not helpful but something. Good luck

Thank you! That is another idea we are floating around. Staying in Santorini for a night or two and then the rest in Naxos it vice versus. We definitely want to stay in Naxos and Crete. Just don’t want to feel too rushed.

Especially with that number of people. It would be hard to move that crew from island to island. I think you could do the day trip to Santorini. Check ferry times. It is a volcano, so there is that point of interest for kids. I did see a youtube video where this mom talked about her family trip to Santorini and her conclusion was that they wished they;d had a week there. But I think in your case there is a lot to be said for a base, and I think Naxos makes a good one...

I don't think a day trip to Santorini would be worth it. It's a long haul. There are numerous closer islands for a day trip including the small Cyclades which are lovely and far less touristy.

Or . . . just spend your entire time on Naxos. It's the largest of the Cyclades with enough to do to keep you occupied for your stay there.

There is also the option of a day cruise to Delos and Mykonos with Delos a fantastic small island devoted solely to it being one of the most sacred of the Ancient Greeks. Superb archeological remains, no one lives on the island, lovely museum and just a few structures for maintenance and archeological workers.

Mykonos is visually stunning but was outrageously crowded while there. Nice for part of the day trip but I wouldn't want to spend a whole lot of time there and this was in October!

The ferry from Athens takes 5 hours on a fast ferry and much longer on the conventional ferry. I wonder if you check out Aegeans web site for seat sales you may find the cost versus time equation makes it much more advantageous to fly to Crete.

As for Santorini. You have to stop there after departing Heraklion. That would be an opportunity to check your bags and take a later ferry to Naxos. That way you can experience Santoini without paying Santorini prices.
The other option is to take the day excursion boat for Naxos to Santorini. It departs around 8:30 and returns around 7 at night but you get a good 6 hours in Santorini. The same boats do Delos and Mykonos plus the small Cyclades as mentioned by tommyk . We have done these excursions to small Cyclades and Delos Mykonos and indeed it is a long haul but all three of them are about the same length of time. If any of them isn't too long a day then they all are not too long.

Thank you SO much! Do you have the name of the line that takes the small day trips out to Santorini, Mykonos, etc or will we be able to find it easily at a port?

The two ships are MV Alexander and Naxos star. Alexander is a cat and has a wide beam. In my opinion it is more stable if the sea is acting up. When you arrive at the port and walk up the waterfront promenade there a several travel agents. Every one of them will be advertising the excursions. Just stop in and ask about the schedule. They used to do the same excursions daily but the last time we were there they do different cruises each day giving you more opportunity to plan.