Itinerary feedback much appreciated

I think the first 3 stops are fairly good, assuming you land in Athens, fly direct to Chania, ferry from Heraklion to Santorini (I hope v much on a Fri or Sat, because of fewer huuuuge cruise ships), then on to Naxos. Hope you are aware this is a late-start on accommodations for these hugely popular sites, at the height of high season, even if you have deep pockets... especially since you want to find local-owned lodgings Are you doing arrangements on your own, or thinking o using an agency. If the latter, I strongly urge you to use an Athens=based agency ... US agencies often just use a formula, do not know or use the kinds of accommodations you want. In Athens, agencies with good reviews on these forums, include Fantasy travel and Dolphin Hellas. Altho even these may not be able to supply your dream accommodations. I have stayed in great places like those... but began contacting them in January most yeara.

I gather that the 1 night on Mykonos is in order to make that Samos ferry connection. Samos is such a BIG island, with so much to discover, that I'm making a guess that you're again using it as a "hop stop" to get somewhere else, such as Turkey. Otherwise a bit mystified. In Vathy, Samos, there's aa little-known terrific arch. museum housing the Biggest ancient Kouros sculpture ever unearthed (they had to lift the ceililng of the room built for it). But since you say not intoo ancient history, I guess that's not your motive. Interested to hear more.

Janet, thanks so much for your reply, sorry if I was not clear, we do fly to Crete after a connection in Athens and fly out of Samos, I was trying to avoid backtracking so went with that option on airfare. I was going to skip Santorini altogether due to crowds but my daughter wanted to see it and we apparently do have to go through there for this route ferry wise, and unfortunately we are there on Wednesday - cruise ships-ugh. If I'm too late in the game I will have to accept more standard accommodations and it does indeed sound like a good plan to use an agency so thanks for the recommendations. Again thanks so much and if you would suggest any other changes I can make them now before I begin to book lodging.

I have no further comments to add to those given by Janet.

Regarding this final journey from Naxos to Samos via Mykonos, you could avoid spending a night in Mykonos by taking the 9:00 a.m. Seajets from Naxos to Mykonos and catch the 12:15 p.m. Blue Star ferry from Mykonos to Samos.

With your plan you'll waste a lot of time on this journey by spending a night in Mykonos, which is hell in the summer unless you want to party all night (great for avoiding having to find accommodation! lol).

All this just to end up spending only one full day on Samos.

Unless there's a good reason to go to Samos (i.e. it's a stepping-stone to Turkey?) I would drop both Samos and Mykonos for this trip, freeing up 3 nights.

Add two of those nights to Crete, which would then put you in Santorini on a Friday instead of Wednesday. And add the other night to Naxos, giving you time to take a day trip to Mykonos so you and your daughter can at least get a taste of it.

From Mykonos you can fly direct to Gatwick London, Geneva, Amsterdam (twice a week), and other European airports. The same would be true flying from Santorini.

Thanks again all, I really should have consulted this forum before buying airfare into Crete and out of Samos since flying out of Naxos is another $1000 for some reason and involves a 28 hour journey back. So I think my best option is
1. Keep this airfare and dont stay on Mykonos and instead take the 9:00 a.m. Seajets from Naxos to Mykonos and catch the 12:15 p.m. Blue Star ferry from Mykonos to Samos. So that trip would look like this, Crete 7 days, ferry to Santorini and not be able to avoid huge cruise ship hell, 2 nights Santorini, then onto Naxos by way of Mykonos but not staying in Mykonnos, 4 days on Naxos, then 3 on Samos.
OR does anyone have any other suggestions as to other routes and I could look for airfare for that?

I really appreciate the much needed help as Im now concerned that I really screwed this up. And by the way Im a Physiccal Therapist / Physiotherapist and would be happy to remotely help any of you who are having issues with pain or dysfunction since I have unique methods and tools to do so that can be applicable remotely. Just want to pay it forward and help you all enjoy your next adventure ")

It also looks like I could fly into Crete and out of Santorini but omitted that option to avoid backtracking, wonder if I could still do crete, santorini and another island but backtrack to Santorini to fly out. Also flying out of Athens is definitely cheaper but it seemed too far.

I could still do Crete, Santorini, and another island, but backtrack
to Santorini to fly out.

Yes, there are quite a few options from Santorini.

Take a look at the ferry departures from Santorini:
I set July 15th, you can change the date.

https://gtp.gr/greekferries_searchresult.asp?Code=EGRSKY22&AskDate=15%2F7%2F2025&IsDep=True

Regarding the return trip to Santorini, just click on the green "Change to Arrivals" button and change the date.

A little overwhelmed by the options? Remotely, and without being a therapist, I can recommend Amorgos Island without any prescription :))

A real Greek island, not a zoo for Instagram-loving tourists.

https://amorgos.gr/

On gtp.gr, it's listed as Katapola, one of the two ports of Amorgos, accessible from Santorini.

Schedule for mid-July:

http://www.openseas.gr/JTR/AMO/2025-07-15/2025-07-15/itineraries

I would take your one day in Mykonos and give it to Samos. That will eliminate one ferry, which will be helpful. And Mykonos is no better than any other island so don't worry if you feel like you're "missing" it. You'll be having such a great time on Samos that you won't mind in the least.

I would take your one day in Mykonos and give it to Samos

The stopover in Mykonos is just because it is not possible to go directly from Naxos to Samos

Thanks so much everyone as Im clearly in need of help here. Amorgos looks so amazing, thanks Jo Lui, I definitely want to go there, any suggestions on good duration on Amorgos?
I think my options now are
1. keep existing airfare into Crete and out of Samos and do this; Crete 6 nights, 2 nights Santorini, 3 on Naxos, 3 days on Amorgos, then 2 on Samos, but is this may be too much moving around and not enough time on Naxos or Amorgos?.
2. Drop Naxos and go Crete 6, Santorini 2, Amoros 5, Samos 3 which seems a lot less rushed and I'm now really interested in Amoros
3. Attempt to get new airfare into Crete and out of Santorini, use Santorini as base to see Amoros and Naxos? Does that sound feasible?

Again thank you all for your help and seriously LMK if there is anything I can do for any of you in the pain, joint pain, exercise and wellness arena, I have so out of the box things that can be self administered that are game changers for many :)

My suggestion of Amorgos was only if you're returning to Santorini instead of Samos for your fly-out.

You want to visit five islands. In my opinion, that's too many; you'll spend your entire trip unpacking and repacking, going from ports to hotels and back, checking out and in, waiting for ferries, etc.

I can guarantee that in the Greek islands, the more places you add, the harder it will be to plan your trip in a given timeframe.

Our last trip to Amorgos was 6 nights, I can't imagine staying on an island for less than 5 days and we'll be in Greece (again) in a few weeks for 15 nights, we will only go to two islands, + 4 days in Athens on the way back. Only 1 ferry trip and 2 domestic flights. That's it.

That said, a feasible itinerary for you would be (subject to your specific dates depending on the ferry schedules):

Crete → Naxos → Amorgos → Santorini

But also be aware that just one day of bad weather with a canceled ferry can completely change all your subsequent trips and reservations. I've experienced this a few times.

So, think twice...

JoLui has good advice for you, if you can easily change your return airports from Samos to Santorini. Amorgos is a beautiful island.

But Samos is beautiful too. Be assured, as a first-time visitor to Greece, you can have a great experience on almost any island. Samos has plenty to keep you busy for a couple of days. There are two main harbors -- Samos (Vathy) and Pythagorio. I'd recommend staying in the latter ... it's a little more vibrant and "touristy", in a good way. You can rent a car for a day and explore the island ... lots of lovely little beach towns and mountain villages. There are beach excursion boats too, which your daughter might enjoy -- you can check into this (and the car rental) the night you arrive. It's a quieter, less touristed island than Crete, Santorini and Naxos, which might be a relief at this stage of your journey. But still beautiful scenery, amazing food, and friendly people.

So before you make the change, consider just keeping your latest itinerary ... Crete, Santorini, Naxos, then Samos (via Mykonos). And then get busy with your hotel reservations. We can help you work Amorgos into a future trip.

Pythagorio is next to the Samos Island airport.

Thanks again to all you wonderful people! I agree it would be simpler to leave my current airfare (into Crete, out of Samos) and get my "non super touristy fix" in Samos, then work Amorgos into next trip. My plan is; Crete 7, Santorini 2, naxos 3, Samos 4
OR
should I do Crete 6, Santorini 2, Naxos 3, Samos 5?

Thanks again all!

Crete is huge. I would keep the more days for it.

I’d do Crete 7, Santorini 2, Naxos 4, Samos 3.

Great, Ill do Crete 7, Santorini 2, Naxos 4, Samos 3.

I want to stay at Enagron Ecotourism Village for the first part of out stay which is located near due West of Heraklion near Axus and Livada for 2-3 nights since my duaghter wants to do a farm stay type thing and she is studying sustainable forestry and agriculture. Any suggestions on where else to have a second base near Chania? We defiantly want to do the Samaria Gorge hike ant at lest a few other good hikes and would prefer closer access to beaches for that part of the stay. Also thinking just staying in 2 places vs 3 but understand Crete is big so could do 3 bases if better. Thanks again all :)

And we will have a rental cat the whole time, thanks