Itinerary

Please add number of days and time of year--arrival and departure times can also make a difference. Without those details, it is nearly impossible to offer much in the way of advice.

According to your previous post it's a three week trip in September 2023.

As Janet and I told you in response to your January 10 post, your biggest concern will be to traveling between the Cyclades and the Dodecanese Islands.

In your project you want to do this trip twice. A first time from Crete to Rhodes and a second time from Rhodes to Santorini.

These trips cannot be made by direct flight, and according to the ferry schedules of previous years there are provided once a week either by Anek Lines or by Blue Star or Seaspeed Ferries

Anek Lines operates the Rhodes-Santorini route once a week. The trip takes about 16 hours.

Same for the Heraklion - Rhodes route. Once a week. 16 hours

Seaspeed Ferries company also operates once a week the Rhodes - Santorini route (via Crete), Trip duration approximately 19 hours.

Blue Star ferries have not published its schedules for September between the Cyclades and the Dodecanese Islands, it is possible that it will go a little faster but it will also be once a week and a minimum of 11 hours.

As discussed in your original thread, the ferry trip from Crete to Rhodes takes at least 10 hours and the same time to return. I am assuming knowing that you are planning to fly.

We actually did exactly that trip once. We started in Crete then took the earliest flight from Chania to Athens and immediately transferred to a morning flight to Rhodes. As I recall we were in our hotel room in Lindos by 11am. That plan works well.
However you now have to get from Rhodes to Santorini. You are going to have to use the same strategy. Fly Rhodes to Athens then fly to Santorini.

Or you can do this trip on a logical pattern.
When you arrive in Athens fly immediately to Rhodes. Then fly Rhodes to Athens then to Santorini. Ferry Santrrini to Naxos and ferry or fly back to Athens for the end of your trip.

You will have a more simple plan if you drop Rhodes.

I think you should save Rhodes for another trip, when you can focus on the Dodecanese islands. There are some truly amazing sights in Rhodes and Kastellorizo and Tilos and Nisyros. Just a short ferry ride from each other. Easily enough to occupy 2 or 3 weeks.

When I first started visiting Greek islands I did what you’re doing … made a list of places I wanted to see and twisted myself in a pretzel (to use Janet’s term) trying to make it work.

So much better to simplify & really enjoy Greece than to run from airport to airport to ferry. Add those Rhodes days to Crete, and when you get home, start planning the Dodecanese trip.

Check out Windstar cruises. I found the most perfect itinerary that leaves September 10. It includes your islands, except it stops at Patmos not Naxos and it includes Nafplio, Monemvasia, and Ephesus as a bonus.

I think this is more than necessary for only three weeks but if you do it there are three extra-long travel legs here: From your point of origin to Crete (which is where I would recommend you begin), from Crete to Rhodes (eight-hour ferry), Rhodes to Santorini (5-hour flight but door-to-door that is eight hours) and Naxos to Athens. Oh, shoot, that's four extra-long travel legs. Grueling.

How about substituting Amorgos for Rhodes? That's only about 90 minutes from Santorini, which is easily reached from Crete. And then Naxos is right next to Amorgos. Now your long travel days are only from your point of origin to Crete and from Naxos to Athens. You could include Syros if you're hell-bent on adding another island that is "on the way" to Athens.

There is a way to do it NOT In March-April, but from May onward ..

• ARR ATH Airport. Allow 2 hour lay-over,.
• Fly Aegean or SKy-Express to NAXOS. 5 nights recommended
• 1 pm Blue Star Ferry (2 hrs) to Santorini. 3 nights recommended
•  late afternoon fast=ferry (2 hrs) to HERAKLION CRete
-- at least 5 days recommended (First to Chania, then to South Coast? end in HEraklion)
• FLY To Rhodes (there is now a daily 7 AM Sky Express Heraklion - Rhodes town)
• RHODES - 3 days if mainly Old Town & LIndos.. 5 days if you rent car to explore
• FLY to ATH (numerous flights) ... recommend at least 3 days for major sights, museums

... this is the only sequence that avoids backtracking, and minimizes transit time. And these days, if you plan far enough ahead, and get promotional prices on flights, the price difference between a flight and a fast-ferry is very little.

Janet
We are interested in your suggestion and think your idea is much better than our plan.
I have investigated travel from Herkalion to Chania but not sure the best way to travel. We have no desire to rent a vehicle due to some eye issues. We are not opposed to buses but I was trying to find something a little nicer ..... yet affordable.
Also, trying to find something available without having to spend a night in Herkalion on front and back end of trip to Chania.

Karen, Karen, I think you may be one of those US car-folks who's never taken public transportation. Many Americans think of slow bus routes in inner cities, used mainly by rowdy kids or those unfortunately unable to afford cars. Welcome to a new world! In Europe, busses are very different, especially Greece -- which has almost no rail network as an alternative. The national intercity bus networks in Greece, called KTEL, use modern up-to-date reserved-seat busses, A/C, upholstered seats w headrests/footrests, used by EVERY level of society. Between major towns, frequent schedules, prompt service. So please don't seek "a little nicer." These are nice.

Your ferry from Santorini is due to arrive at 7:30, I think. The KTEL Bus station with busses for CHania is right by the pier. If you're off the ferry promptly, you probably can catch the 8 pm one... if not, then buy a ticket, sit at a cafe for a drink & snack & take the 9 pm. It's about 2 hours... and if you have a rollable bag, most Old Town hotels are easily reachable from Bus Station. I recommend you do some homework on websites, maybe google 3-D, for Chania and Heraklion.

Janet thank you for your reply. Like your plan! Our travel in Spain on buses was an experience that we choose not to have again.
We do laugh about it! However, do not want to do it again. Sounds like the bus system in Greece is better.

Glad I could be helpful! My experience traveling around Greece, on islands and mainland, makes me wistful.. wishing that the so-much-wealthier USA govt would support regional public transportation better than it does. Alas, so many states wedded to the private automobile (ahem ahem) seem to elect Congressfolk who oppose public transit. As a retiree on limited income I am fortunate to live where I do, but find it hard to visit relatives.

I have been to Greece four times and found that the best way to see the islands like Corfu, Crete, Mykonos, Santorini, and more is one a cruise.

We almost missed our ship when the city bus from Athens to the port did not make it's scheduled stop. Instead of being picked up we had to wait for the next one and there was a huge crowd since many were in the same boat (no pun intended). We were told this was not that unusual. Just food for thought.

Windstar cruises = $$$$$$$$