Greek Island Hopping with kids

The logistics of island hopping for the islands you are looking at makes sense. There is no back tracking involved. Although your wish to fly back to Manchester from an island complicates things a bit.

I am assuming that it is your intention to fly to Crete directly from Manchester? You could make your first island hop from Crete to Santorini and immediately catch a connecting ferry to Naxos or Paros. The ferry connections to both islands are good. You can likely be at your hotel on Naxos by 2 in the afternoon.

For your return you can island hop back to Santorini where presumably you can get a direct flight home. Generally speaking 3 nights in Santorini is probably enough. Its certainly as long as my budget can afford.

Crete is very large and you could just spend the whole time there. We have spent many weeks just exploring the west of Crete over the years. Once we spent 3 weeks in East Crete and didn't see it all. Since every island hop will take up a minimum of half a day maybe consider just doing Crete.

I agree with Stan that you could spend the entire 3 weeks on Crete. We are planning a trip of 11 days for next May and are having to make very hard choices.

But if you want to island hop here are a few thoughts.

1. I have been to Santorini and did not think it was very child friendly. Now if the adults want to go--I understand but I wouldn't stay too long there. Beaches are not child friendly, lots of crowds and steps.

2. We loved Naxos and even as we were there with our young adult children, I couldn't help but think that the island would be a great place with younger kids. There is a bit of everything. We stayed at St. George, adjacent to Naxos town, and would recommend. It is walking distance to a shallow beach that would be great with kids. We stayed at Kymata which I also would recommend. We stayed in the roof top suite which has a separate room with two beds and a door that would be perfect for your boys. It has its own TV and a/c. The roof top has a fabulous view and we ate take out dinners two nights there. We had food delivered and the front desk, who are marvelous helped us. The breakfast buffet was wonderful.

3. I have not been to Paros but picked Naxos over it.

I would consider spending 3-4 nights on Santorini (we spent 3 and were happy with that) and dividing the rest of your time between Crete and Naxos, skipping Paros. But Paros is very close to Naxos so could go there too.

Rather than looping back to Santorini to fly home, you could fly to Athens from Naxos (or Paros if went there as well) and spend last night in Rafina at Hotel Avra. They have a shuttle and it is a real town not an airport hotel. This is what we intend to do on our trip. Personally I would rather take an afternoon flight to Athens and leave the next day from Athens then double back in the ferry to Santorini. But then I am not that fond of ferry rides, having a very rough one going from Santorini to Naxos. Or perhaps you can get a connecting flight from Naxos or Paros that requires a change of plane (but on one ticket unlike what I proposed) that would be more efficient to get to Manchester. But there certainly won't be anything direct. I am in U.S. so such tickets are quite pricey but you are in a different market.

Thank you for your advice, we really appreciate it.
I think flying to Athens sounds like the best option. Now to get planning!

Ok since you are now prepared to fly home from Athens then as I stated in my post your island sequence works well. Heraklion Crete to Santorini ,Santorini to Naxos, Naxos to Paros and Paros to Athens on a flight. This works just as well for you to go to Paros then to Naxos.

We to have stayed at Kymata. The top floor room with the second bedroom is probably your absolute best option. Kymata is only a few meters from St George beach which is great for the kids and the bonus is that room has a 180 degree view from the ferry port all the way across to Paros.
Also to support Beths suggestion its not a very good idea to fly to Athens the same day of your return flight. Get there the day before. Hotel Avra is an excellent choice. It is close to the main square for dining and has access to a beach as well. The shuttle service was great and it got us to the airport in time for an early flight next day.

Here is why you are going to enjoy Naxos. It takes a full week to really explore all the island has to offer.
Naxos town https://www.flickr.com/photos/stanbr54/albums/72157632094558042
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Naxos 2019 https://www.flickr.com/photos/stanbr54/albums/72157711294807761

I agree, flying to Athens is the best option for sure. From a general perspective, I've always looked back at the trips to Greece I've taken when I was younger with fondness. However, I will say, the trips I have taken that involved less moving around, and I got to stay in one place, were a lot more enjoyable. There's so much to see no matter where I am! It also depends on how long you are. I think no matter what you come up with, your family will love it!

However, I will say, the trips I have taken that involved less moving
around, and I got to stay in one place, were a lot more enjoyable.

That's how I feel about it exactly. And I don't know about your children, but most children I know are less interested in sightseeing than in exploring. So I would rather explore one island with them in more depth, leaving out another one instead.

Your itinerary is certainly doable. However, if I got to spend three weeks with your choice of islands, I'd either make that three weeks on Crete (Crete is a continent, not an island...), or three weeks on three different Cyclades islands, and save everything else for some future trip. Santorini and Naxos are obvious choices, and Paros certainly isn't a bad choice for a third one. Mykonos is pretty but too much of a party island; wouldn't be my first choice with kids. Tinos might be another island to look into. I only know it from a day trip from another island, but it seemed like a nice island.

I have been to Santorini and did not think it was very child friendly.

To be quite honest, that was my impression on most Greek islands we've been to (and we've been to a lot). Not because the Greek people aren't child friendly (I am sure they are). We simply never saw a lot of tourist families with children. Wouldn't children wish to find playmates their own age? That's kind of hard if they are the only children far and wide. But then, Covid may forbid that anyway.

Well, I have only been to three Greek islands-Santorini, Naxos, and Samos. Both Naxos and Samos have lovely beaches. In both places, I saw lots of families at the beach with children.

Thank you. We had originally planned to just do 3-4 Cyclades islands and then we saw Gordon, Fred and Gino in Chania in Crete and it looks lovely. Maybe we’ll save Crete for another time instead as a few of you suggest.
So, if we did Cyclades, would you still recommend flying to Athens rather than directly to Santorini or Mykonos? I’m guessing if will be cheaper but I thought it would be more hassle with kids.
I did look at Tinos and that looks lovely so we’re open to which islands we do but I definitely want to do about a week in Naxos as I’ve heard such good things and you guys have confirmed that.
Which others would be on your itineraries for the other 2 weeks?

If I remember correctly, the standard ferry route goes from Piraeus to Santorini, stopping at each of these eastern Cyclades islands (Ios, Paros, Naxos, Mykonos, Tinos, Andros, Syros), so you can basically pick and choose along that line. Naxos is the hub from where you can go to other directions like the western cyclades or some of the more remote places like Amorgos.

So you could make Santorini your starting and ending point, or Athens, but if the latter, you are going to have quite a long ferry ride at the beginning. What I would do is look into open jaw options: starting in Santorini and working your way up, ending your trip in Athens.

In both places, I saw lots of families at the beach with children.

Our different experiences with that may depend on the time of year. Families with children obviously can only travel during school vacation. I see that the OP is planning on traveling in August, and many European countries have their school vacation at that time.

One note on that: I hope you are o.k. with heat, because it can get pretty hot during that month. And since it's school vacation time for many parts of Europe, it can also get pretty crowded, which will unfortunately also reflect on hotel rates.

If you can fly direct to Santorini, I certainly would do that unless not reasonable to so price wise. Many of us are coming from North America where such possibilities don’t exist which is why they are not mentioned. I would buy a multi city ticket into Santorini and back from Athens. Then can buy a separate ticket the night before your flight from your last island back to Athens.