Greek Islands – island hopping advice

There are several things wrong with your itinerary. The main one being that you can't visit all of these islands in just 12 days (11 nights).

When it comes to island hopping in Greece: Less is more

Allowing 2 days on an island means that you will only stay there one night.
Any trip from one island to another takes a good part of the day. You have to:
Packing your luggage, checkout, transfer to the port, waiting for the ferry, traveling on the ferry, transfer from the port to your accommodation, checkin, unpacking your luggage.

This means that you will actually only spend a few hours and one night on the island before having to leave. Whatever you would like to do or see, it will not be possible.

So, you have to reduce the number of islands. With 11 nights including a last night in Athens, the reasonable is to visit 2 islands max.

And since you made the mistake of booking the first 4 days in Santorini which is the island that does not match your preferences at all, I don't see how to help you but I can already warn you that keeping your itinerary as it is will be a waste of money and vacation time.

If you can't cancel Santorini, add either Sifnos or Paros. And return to Athens from one of these two islands.

Listen to JoLui he is absolutely correct. Greece is best appreciated slowly. Your plan is handicapped by the ferry schedules to and from each island.
Concentrate on where you want to go after Santorini since that is set. Choose an island on a direct ferry route from Santorini. In my opinion/experience, the best Options would be Paros and or Naxos. Either one will be a good companion island with Santorini and both need at least a week to truly experience and explore. They both will provide a more realistic Greek experience in contrast to Santorini.
How long do you have for Athens portion of your trip? You need plan to be there at least the day before your return flight.

Also note that the ferry trips you want to make on your itinerary will only be possible 90% with Seajets fast catamarans.
For two passengers it will cost you around €600.

For some ferry journeys you will have to get up before 7 a.m., for others you will not be on the arrival island before 7 p.m.

Thanks for the replies!

To clear up a few things:
• I gave a bum steer saying ‘2 days’. I meant 2 NIGHTS on each of those islands, so by that I meant we’d have 3 full days on each. On some of the smaller ones, might that be OK?
• Athens days are not counted here, they are outside of these days, so these are purely for the Cyclades. Once we are back in Athens we will be picking up a car and heading north on a road trip (we won't book the car until we know what's happening with island timings – don't need to worry about making a flight or anything like that, bit flexible there).
• We are coming from Australia, Santorini is the only one that's easy for us to fly into, which is why that was chosen, and it is also at the far end of the islands, so the thinking was, start there and work our way back to Athens by hopping islands, using the ferries.

Agree we probably need to thin down the amount of islands and bump up the days on the chosen islands. Paros is up the top of choices, Naxos seems more for families, but totally open to that if I am wrong there.

With the Seajets fast ferries, we have also included that in the budget, as speed is the priority over cost for those trips, although I agree the other ferries are waaaaay cheaper but soooo much slower and not available every day. Good tip though, thank you. We will switch to those if we are lucky and the timings work.

How about this? (total can be 14 nights)
(flying in) Santorini 4 nights
(ferry) Paros 4 nights
(ferry) XXXX* 3 nights
(ferry) XXXX* 3 nights (must be able to ferry back to Piraeus)

*These 1 or 2 XXXX islands are to be determined for the remainder of the nights. Can I get some suggestions for these, as there are so many and they all look amazing. We are open to any of the islands – Tinos, Ios, Naxos, Sifnos, Syros have all been in the mix at some point, open to absolutely any of them that work though. Paros can be moved or swapped, depending on what works.

With a stay of 14 nights, your new schedule is much better. As for the number of nights on each island, it's up to you.
4 nights is the minimum, however 4 nights on an island means only 3 full days.

If this was my trip I would only go to 2 other islands after Santorini. I take the time to visit the places I go. And I always rent a car on the islands so I can explore how I want, when I want. But since it's your trip, it's up to you

I know all the islands you have chosen, I have been to Paros and Sifnos several times for a total of almost on month each, I would still need about a week more to claim that I know very well these islands.

In Paros, Naoussa, this small fishing village has become the least authentic place on the island. Very promoted by social media influencers, it is now a destination for honeymoon packages with lots of high quality product boutiques and expensive restaurants. In my opinion, like Mykonos, it now looks more like a Las Vegas themed hotel than a Greek fishing village.

Naxos is the largest island in the Cyclades, I only stayed there for around ten days exploring the island by car every day... I don't think I know it well enough. It could be a good choice too.

Paros, Sifnos, Naxos are good choices. Folegandros too but it is a small island (barely 600 inhabitants) and very quiet, especially in May, with very few accommodation options.

You didn't mention Amorgos which is one of my favorite islands, 1h30 from Santorini.
From Amorgos you can reach Paros or Naxos then finish in Sifnos before returning to Piraeus.

https://amorgos.gr/

(there are two ports in Amorgos: Katapola and Aegiali)

Tinos is also possible provided you forget Sifnos / Folegandros in your itinerary. Daily ferry routes are incompatible with these islands. And ending with Tinos means that you return to the port of Rafina and not to the port of Piraeus.

Regarding the order in which to visit the islands you need to look at the ferry schedules on your dates.

ferryhopper is a good website to check timetables

https://www.ferryhopper.com/en/#/

Also try openseas which shows you the schedules for an entire week

http://www.openseas.gr/

Please note the first week of May is Orthodox Easter week with many Greeks traveling on the islands.
May 7 will be probably a day of ferry strike.