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3 week itinerary help needed

We are two couples planning a 3 week trip September 2025, nothing is scheduled and we are somewhat flexible.. I have done lots of reading and my head is spinning. Our loose plan is to divide the trip into 3 parts
-Two Islands in the Cyclades, leaning toward Milos (4 nights)and Sifnos (3 nights).
-Peloponnese- Nafplio (3 nights) Kalamata (3 nights),
-Meteora (3 nights), Stop in Delphi for a few hours on our way back to Athens (2-3 nights)
I realize that there is travel time to consider and that travel takes good chunks of the day. I am looking for input on how to make this come together. Once I have the Itinerary, I will dive deeper into the day trips from the bases. Any help would be very much appreciated!

Posted by
2781 posts

We spent 2 nights in Meteora and 1 night in Delphi and that allowed us to see most of the monasteries and we saw both Delphi and the museum. Delphi is very small and I would think 1 night would be adequate.

I would add nights to Peloponnese.

Posted by
1923 posts

I just got back from Greece. I would agree with Beth that two nights in Meteora would be sufficient. And I'm not sure it's necessary to visit all the monasteries. I only went to two of them (I was on a tour), and I didn't feel shortchanged by not visiting more of them.

Two places we went that I would highly recommend:

I also visited Naxos on my own at the end of the tour. I can't compare to any other islands, since I didn't visit any of the other Cyclades. But I loved it.

Posted by
2315 posts

I also think that your stay in Meteora can be shortened to 2 nights. But maybe you also want to do some hiking in the area or, being motivated by spiritual desires, you want to do more than just a basic visit to the monasteries and leave once it's done.

It's up to you.

While Nafplio can be an interesting base that has its charm and allows you to visit a few places within a 40-minute drive, Kalamata (which I know) is in my opinion not the most pleasant place to establish a base given that you seem attracted to touristy places. The city of Kalamata is not strictly speaking a very touristy place, at least for a non-native Greek. And above all, there are quite a few other places in the area with more charm than this big city.

But as you don't say why you are thinking of Kalamata as a base for 3 nights it is difficult to advise you on another well-located place.

As you have noticed, travel from one place to another in Greece is very time-consuming and often underestimated.
So consider that your 7-night stay in the islands (Milos-Sifnos) will include the equivalent of 2 full days of transfer from one place to another, or 1/4 of your stay in the islands.

I don't know what made you choose Milos, maybe the countless photos on Instagram of the lunar beach of Sarakiniko now transformed into a marketing object, but as for many regulars in the Cyclades islands, Milos is far from being my favorite island, so I will stay at least 4 nights in Sifnos