Greece Pre-Tour Itinerary: Which Islands?

You should find a way to fit in Mykonos because it links you via a 40 minute ferry ride to Delos the reputed birthplace of Appollo and Artemis which is designated as a World Heritage designated site and has plenty to see. The other two islands with the most historical significance are Crete (Knossos Palace) and Rhodes (site of Collossus, one of the 7 Ancient Wonders of the World).

Be aware that ferries are weather dependant and if a storm blows in, as they can do in October, your travel plans could be scuppered. Also the ferries are subject to strikes, but you usually get warned of strikes a week or so before hand.so can make other arrangements

Crete is definitely worth a longer trip with a long history and some tremendous sites ranging from Minoan palaces, Roman towns Venetian forts and Ottoman mosques.

Given that you only have one week, you won't have time to go to more than 2 islands.
Bad weather causing delays or cancellations of ferries is also a possibility to take into account when you make a lot of trips in such a short time.
So don't try to make a record of island visits, but make sure you enjoy the places where you will be.

About your thoughts on possible choices:

1) 2-3 nights Heraklion; 2 nights Santorini

In my opinion, Crete is too large to stay there only two or three days, especially if you don't want to rent a car.

Santorini, even if in October is quieter (although this year it is likely to be very busy even in October), is as you say a mixture of a shopping center on a sales day and a blue and white Disneyland, especially if you don't stay long enough to see anything other than the main "attractions" for cruise passengers and Instagrammers.

2) 2 nights in Heraklion; 1 night in Santorini; 3 nights in Milos

By eliminating Crete and Santorini as in option 1, only Milos remains

You can consider 3 nights in Milos as the first island since it has an airport and then go to Sifnos by ferry for the other 3 nights.

> 3) 3 nights in Paros/Antiparos OR Naxos; 3 nights in Sifnos OR Milos

3 nights in Paros/Antiparos OR Naxos...

Even if the majority of the members of this forum will advise you to choose Naxos there is no reason to favor Naxos over its neighbor Paros. Each island has its advantages and disadvantages and both have an airport.
To each argument for Naxos I can give one for Paros, and vice versa.
Naxos is bigger, greener and more mountainous but these are benefits you won't be able to enjoy in just 3 days.

3 nights in Sifnos OR Milos...

From a practical point of view, from Milos you can take a flight to Athens. Sifnos does not have an airport, you will need to take a ferry. And it does not have a few lunar landscapes like Milos but has many other advantages, its authenticity, its beauty, its gastronomy, a very good bus network (better than in Milos), superb and easy hiking trails, and the authentic blue and white villages of your dreams.

That said, an important parameter is the period of October. From October 15 a large part of the accommodation and restaurants will close. The more touristic and larger the island, the more choices you will have.
Which unfortunately does not plead for Sifnos if you are looking for a minimum of animation.

So, taking into account the preferences you have given, I would keep
Milos
Paros/Antiparos
Naxos
Sifnos

By staying 3 nights on each island (if you optimize the travels)

In April, I did your first choice--Heraklion and Santorini. And the same number of nights.

I could have stayed in Crete an entire week there is so much to see. I only spent three nights.

I also took the same ferry you're thinking of to get to Santorini.

Santorini is interesting. I really enjoyed the excavation at Akrotiri. The island is beautiful and the sunset views for Oia were amazing. Yes, Santorini can get a little touristy but mostly, I felt, in Fira and near the beach. While I probably wouldn't want to spend a week there, I'm glad I decided to go. I spent two nights and with the early ferry gave me 1.5 days. It was enough for me.

I had been putting off going to Greece and now I'm sorry I did. I loved it. I'm going back in the fall.

It's really not worth going to Crete for just a few days. It's the largest of the Greek Islands and deserves weeks to fully experience.

I would pick two of the smaller islands that are closer to the mainland for your 7 days and especially islands that are fairly close to one another and on the same ferry route.

There are several in the Cyclades that may work for you like Sifnos/Milos or Naxos/Paros or even Tinos/Syros.

I've been to Sifnos, Milos, Naxos and Tinos and I can highly recommend them. Haven't been to Paros or Syros but from all accounts are worthy of a visit.

Don't overlook Aegina/Agistri the two closest islands to the mainland with Aegina having everything one would want in a Greek Island and Agistri known for it's family atmosphere and beaches.

@dhkhuff - Thanks for the suggestions of Delos and Rhodes.

Although I would like to see Rhodes, I will probably skip it on this trip. Turkey winds on my travels frequently, and so I am thinking that Rhodes would make sense next time I visit Fetiye or Marmaris.

Your suggestion of Delos is moving up on my radar. It appears that one can get to Delos from Naxos or Paros as well as Mykonos. I am exploring whether that might be another option for me, even if it means spending an extra day in the islands.

Thanks, @lanlubber, for reminding me of the possibility of a ferry strike or bad weather. I have an extra 24 hours of padding at the end of the excursion, which might provide some breathing room. Still, it's a good idea keep an eye out for possible interruptions and make sure my accommodations are refundable.

I agree about Crete. It's a big place that is probably worth a longer trip.

@JoLui - Thanks for taking the time to share your thoughts. You have given me some good things to think about. I agree that it would be better to spend more time on fewer islands.

I should have mentioned that the RS tour begins on October 2, and so I actually would be visiting the islands the last week of September. I think I will be there before things start shutting down.

@Frank II -- My first thought when I started the pre-trip planning was that I wanted to see Minoan stuff and Santorini. Maybe that initial reaction was the right one. It's good hear that that itinerary worked well for you. It's also good to hear that you didn't find Santorini too touristy.

@tommyk5 - thanks for taking the time to respond. Everyone seems to be in agreement that one needs more time on Crete.

I haven't looked much at the Saronic islands because the RS tour goes to Hydra. I want to try something different for the pre-tour excursion.

We returned from Greece at the end of May. We spent 3 nights on Santorini and loved it! It is unique and the views of the caldera are stunning! There are crowds but in May it was manageable and did not ruin our trip. If you spend 3 nights in Santorini, then you would have a day to rent a car which will give you the chance to see the rest of the island. There is more to Santorini than just the caldera views. Visit the archaeological site at Akrotiri, the red sand beach, the Akrotiri lighthouse, the black sand beach in Perissa.

We also spent 4 nights in Naxos and loved it! It's a beautiful island and very, very different from Santorini. It's quieter and more laidback. We also rented a car for a day and drove all over the island, stopping at lovely small towns and fishing villages and saw beautiful inland and coastal scenery. It's a very easy and short ferry ride from Santorini to Naxos (2 hours).

While on Naxos, we did meet people who visited Paros and they raved about Paros, too. You would take the same ferry (Blue Star Ferries) from Santorini to Paros. It stops at Naxos first.

By October, Mykonos will be the only island with day trips to Delos. So, find out if Naxos or Paros still has trips to Delos in September.

@leonard - Thanks! That thought had crossed my mind. The boats from Naxos/Paros to Amorgos definitely stop sailing at the end of August. I think the boats to Delos/Mykonos continue through the end of September, but it's on my list of things to double check before I finalize any kind of itinerary.

The possibility of a day trip to Delos and Mykonos from Naxos or Paros definitely increases the appeal of Naxos/Paros/Sifnos itinerary. It would add a major archaeological site and give me a chance to take a quick peek at a hugely popular (over-touristed) destination without breaking the bank.

Marie, for more certainty about Mykonos day-excursions, I suggest something "old-fashioned" -- use the email link on the website to write an actual e-inquiry. I have done that in previous years (re Start-date of those day-trips ), got a prompt useful response, different from info on the website... conditions & demand may cause date-changes. Also, always good to be polite ("appreciate very much your help") ... in Greece I've found manners matter.

The boats from Naxos/Paros to Amorgos definitely stop sailing at the end of August.

The boats for Amorgos do not stop at the end of August. You will find several possibilities every day between Naxos/Paros and Amorgos in September, October etc. With Seajets, Blue Star Ferries and the Express Skopetilis of Small Cyclades Lines. The ferries operate all year round, they are not just for tourists, they are the main means of transport for people who live on the islands and the main means of supplying food, various equipment, and materials.

The possibility of a day trip to Delos and Mykonos from Naxos or Paros definitely increases the appeal of Naxos/Paros/Sifnos itinerary. It would add a major archaeological site and give me a chance to take a quick peek at a hugely popular (over-touristed) destination without breaking the bank.

In Naxos or Paros you will find several travel agencies that offer day trips to Delos. In Paros departures are from the port of Naoussa in the north of the island. The price varies between 50 and 60 euros and does not include access to Delos which is 8 euros (in 2022). Access is free on the last weekend of September (European Day)

Since your trip is scheduled for September 2023, you have plenty of time to view these details of excursions and ferry schedules. The priority is to know which islands you want to go to, find the accommodation that suits you and look at the September 2022 prices to get an idea of ​​​​the prices. Use Booking, Airbnb, and Google Maps to find this information.

And don't forget, it's up to you but 3 islands in a week it's too much. It's transforming a trip into a visit to an amusement park and the islands into a ride in this park

Thank you all so much for your responses. The discussion has helped me to crystallize my ideas. My big takeaways are:

• 3 nights minimum at each stop;
• 2 islands max (for a week of travel);
• Keep my plans flexible in case of storms or ferry strikes;
• I would enjoy either itinerary -- Crete(Knossos)/Santorini, or Naxos(or Paros)/Sifnos(or Milos). One really can't go wrong either way.

Create(Knossos)/Santorini has the blockbuster sites with the drawback of more crowds and higher prices. Naxos/Sifnos seems the slower, more laid back option. At the moment, I am leaning ever so slightly toward the Naxos/Sifnos option, although that may change over time.

If you do include Crete, make Heraklion a day trip from lovely Chania. There is no comparison between Heraklion and Chania. Visit Knossos and Archeological museum, and return to Chania.
I recommend that you visit Paros and/or Naxos.