Greece in September

Indeed your request is a little too broad :))

There are at least a hundred Greek islands that can be visited. About twenty are in the Cyclades (those with the blue domes and white washed houses).

Note that September is now still high tourist season until at least mid-September. It's not as peaceful as it was in the 90s.

See the official Greek tourism website:

https://www.visitgreece.gr/

With 2 1/2 weeks it is impossible to see/visit everything, so you will have to make choices (and when I say visiting it doesn't mean consuming famous places one after the other, it's really visiting and enjoying them)

Here are roughly the possibilities:

Athens + Mainland +1 island (possibly 2) On the Mainland, partially visiting the Peloponnese takes a week.

Athens + Crete

Athens + 3 islands maximum

We want to go to places that aren't very touristy

Avoiding overly touristy islands means avoiding islands with airports.

In the Cyclades the most touristy islands are in order:

• 1: Santorini (2 million visitors / year for an island population of 15,000 inhabitants)

Then come:

• 2/ Mykonos
• 3/ Paros and Naxos
• 5/ Milos.

So if you want to avoid the crowds, choose other islands. Which will mean going there by ferry and not by flight, which with 2 1/2 weeks is not really a problem.

Your best option is to find two islands that are on the same ferry run.

I combined Tinos with Andros (Syros would be another option)

Tinos is a gem of a Greek Island. One of my top 3 favorites.

I also combined Astypalea with Amorgos.

Astypalea has an airport which one would think makes it easy to get to but it's not Big Name Island. When I was there early October it was very quite but very Greek.

I then took a ferry to Amorgos (no airport). Lovely island one of my top 3 favorites.

Depending on what part of Sept. you go can make a difference. If possible aim for the second half.

A number of other combinations available so more research is recommended on your part.

Hotels, transportation, tours, etc. would also require more work on your part once you determined where you want to go.

In September 2019, we spent 2+ weeks on Crete, Greece’s biggest island. September was the time to be there, for decent weather and fewer tourists. It has many archaeological sites from the Minoans, a culture that preceded the Ancient Greeks, Later, but still centuries ago. it was part of the Venetian empire. The year before, at Easter time (April), we spent 2 weeks on the island of Hydra (Rick Steves’ favorite), then on mainland Greece, driving around the amazing Peloponnese peninsula, up through Galaxidi and the ancient sights at Delphi, and finishing with several days in Athens. Having a rental car on both trips allowed us to visit lots of places.

Several places on Crete were not busy or touristy at all in September, compared to other times of the year. We used the Lonely Planet guidebook, plus the Rough Guide for Crete. Rick Steves doesn’t have one, so it’s off the radar for a lot of potential visitors. As we drove through Agios Nikolaos in northeastern Crete, we saw lots and lots and lots of pedestrians heading to the beach, towels and inflatable pool toys in hand. We kept driving.

In southeastern Crete, we stayed in Kato Zakros. Nice black sand beach (although in September the water was a bit cool, but still acceptable - we sure went in), wonderful archaeological Minoan sight a two minute walk from the beach area, good restaurants, and almost zero other tourists.

Other key places on Crete that we enjoyed were Iraklio and its archaeological museum, the ancient Knossos palace sight just south of Iraklio, Pitsidia and the nearby Festos ancient sight, Hania (don’t try to drive in Hania old town), the Samaria Gorge, and Tzermiado on the Lasithi Plateau.

We are thinking of flying into Chania and spend a week on Crete, then a week on Antiparos, and lastly a few days in Athens and fly home. It looks like booking a flight through Expedia (or equivalent) is way cheaper than booking directly with the airline — the roundtrip works out to use 2 different airlines. I’m concerned about the complexities of working with the airlines when the flight is booked through a third party (to buy/book seats. Expedia isn’t letting me select seats for some of the legs.). Any advice on that?

Most experienced travelers recommend booking directly with an airlines to avoid any confusion on what you are getting with the ticket and better customer service.

Many of the third party booking sites usually list the least expensive flight but that flight may not offer checked luggage, seat selection, refunds, rebooking, etc.

If you decide on a third party be absolutely sure what you are getting with the ticket.

Most airlines will list what you are getting with a ticket.

I would be extremely surprised if Expedia offered way cheaper prices than the airlines. It's sometimes the same price but most often it's more expensive

If I compare a Paris→Athens flight with Aegean the prices displayed are the same on the airline and on Expedia.

BUT!

At the end of the booking process the same flight Paris→Athens at €112.51 with Aegean costs €130.51 with Expedia.

The other trap is the options that are more expensive on Expedia.

For example, the selection of extra legroom seat costs €8 with Aegean and €18 with Expedia.

And I'm not even talking about communication problems with third parties in the event of flight cancellation or modification.

I had purchased flights in 2020 directly with the airline, the flights were canceled due to Covid.
The airline refunded me within 48 hours of my request.
I know people in the same situation who booked through third parties who waited months to be refunded, and some who were never refunded

For our 2019 trip, just on Crete, flew Denver to London, then booked London to Crete and back (in at Iraklio, out from Hania/Chania) on easyJet. They’re a “budget” airline that serves the UK, but you have to get yourself to London (or another easyJet airport) to take their flights. And we always book directly with the airline involved. Expedia, Kayak, etc. can be helpful for researching flight possibilities, but book with the airline.

Great suggestions all! I just pumped into an alternative itinerary for islands hopping that starts in Athens, then Evia-Andros-Tinos-Naxos-Santorini. Apart from Santorini which is packed all year round, I really love this concept of visiting less famous or less crowded islands that still can make a trip to Greece just marvellous.

Thanks all! We are now thinking of Naxos instead of Antiparos, based on a local Paros’ resident’s suggestion. Does anyone have experience with travel insurance? The type that covers cancellation of the trip for medical or other reasons? Booking.com seems to have it for UK residents. Couldn’t find anything for US residents. Any suggestions appreciated.

FOrr at least 10 trips I have used Insure My Trip - an outfit that is not tied to one company, offers you a range of companies. I just use them for medical trip insurance (Not for insuring cost of a tour or ship). if you use this link - http://www.insuremytrip.com/plans/package.html - you put in your data, and can pick 2 or 3 of the many options, and you can view them side-by-side to see exactly what's offered, the costs & conditions. Then you can purchase online. OR, if you want a little hand-holding, you can call their number, and NO ROBOTS ... just nice ladies who sound like the folks who work the phones at LL Bean will walk you thru the process & order for you. One tip - request if possible the paperwork (giving all the specifics) to be PAPER, mailed to you, vs. an email which can be endless. Luckily, I've stayed healthy on all those trips, but once when I had a "glitch" regarding I think luggage, was able to use the customer service line from Greece direct to US.