Itinerary Advice - Peloponnese and an island, May 2024

Olympia is farther away from Athens than Delphi. Both are wonderful, but if you can only see one on your itinerary, visit Delphi.

Just a remark.

You arrive in Athens on May 1st which is a public holiday, and you will be there during the Holy Week of the Easter holidays.

Friday 3, Saturday 4, Sunday 5 and Monday 6 are public holidays, the opening hours of the sites may be modified, or for some they will even be closed and the vast majority of businesses will be closed on Sunday May 5 and Monday May 6.

There will be a lot of people on the roads leaving Athens

The good thing is that on Friday the 3rd you will see many processions in the streets of Athens and on Saturday 4 you will probably see fireworks.

Thank you, JoLui. But to clarify: those are note the DATES I am visiting, but the DAY number of the trip. We arrive on May 15, missing the holidays.

My mistake!

The day numbers corresponded to the dates in May (Sundays 5, 12)

It is always a bit risky to fly back from an island on day of international flight. People do it (including my son) but would make me nervous.

I would reverse your trip and add a few days, since you are retired.

Fly to Santorini your first day. You need to allow several hours for an unconnected flight. Stay 3 nights. This will give you 2 days. We did this and a great way to get over jet lag.
Ferry to Naxos. We did this and stayed 4 nights. It wasn’t enough. I would stay a minimum of 3-4 nights to make it worth the trouble.
Fly to Athens. Rent car and drive to Delphi.

Do rest of itinerary ending with returning car at airport and staying in Athens.

Our itinerary was a little bit different than yours but I absolutely agree with BethFL’s suggested order for your trip.

We flew on one ticket from our home airport (Boston) to Santorini with a layover in Zurich. This was our itinerary.

Santorini - 3 nights
Blue Star ferry to Naxos
Naxos - 4 nights
Fly from Naxos to Athens
Pick up rental car
Nafplio - 5 nights
Return car to airport
Taxi to our Athens hotel
Athens - 4 nights

I would not substitute Hydra for Santorini and Naxos.

Spend 3 nights on santorini and rent a car for one day to travel around the island. Do the same on Naxos.

The consensus from other posters is leave Athens for the end of your trip. Jet lag can be overwhelming particularly in Athens.
We always fly to our first island on day of arrival. For connecting flights you need 2 hours to collect your bags, go through passport control leave arrivals and go upstairs to Departures. You check your bags, go through security and get to your gate. Chances are you will have time for your first Mythos beer while you wait for the next flight.

This is what I would suggest.

Fly to Santorini first as there are more flight options.
Santorini and Naxos are great companion island. You get the dazzling caldera views on Santorini and a much more authentic Greek experience in Naxos. Its a short 2 hour ferry hop to Naxos.
Here are some images.
Santorini and Naxos https://www.flickr.com/photos/stanbr54/albums/72157689937827955

Fly back to Athens from Naxos and rent your car from the airport.
We arrived Delphi in mid afternoon and got a hotel and we visited the museum. The museum really sets you up for visiting the site next morning. Staying in the village provides you with some amazing views.
Next day drive to Nafplio. Ancient Corinth is a good site but the spectacular feature is right next door. Be sure to drive up to Acrocorinth. It is a massive fortress with 360 degree views over the countryside.
Corinth Area. https://www.flickr.com/photos/stanbr54/albums/72157711755443483
Nafplio https://www.flickr.com/photos/stanbr54/albums/72157632094108982

We did the drive from Nafplio to Monemvasia. It is an amazing drive with so many interesting sites on the way (don't miss Mystras the last Byzantine city at Sparti) We made so many stops that it took us all day to get to Monemvasia. I would suggest that you do two nights there and drop Kardameli.
The first 40 or so images are Monemvassia
Peloponnese, Mani and Monemvassia. https://www.flickr.com/photos/stanbr54/albums/72157711323535897
Now return the car at the airport and head into Athens.
It is important that you are in Athens at least a day before your return flight.
We were on a flight from Naxos to Athens and had a 3 hour delay. There were Australians, Americans, South Africans, French and Brits who all missed their connecting flights home.
We stayed in Athens for 3 days before our flight home.

Thank you all for your responses - and the pictures! Can't wait for the trip!