Greece Itinerary

Your itinerary seems perfectly balanced to me.

To go from Naxos to Nafplio the easiest way is to go through Athens.
The ideal, instead of taking a ferry, would be to take one of the first Naxos → Athens flights on September 27.

To date there are 3 Sky Express flights scheduled between 9:30 a.m. and 2 p.m.

Then rent a car at Athens airport, and two hours later you will be in Nafplio.

On September 30 you can return the car at the airport and take the metro bus or taxi to Athens or return it to the rental office in Athens.

Regarding the Santorini→Naxos ferry on September 23, see the schedule here:

https://www.ferryhopper.com/en/#results?itinerary=JTR%2CJNX&dates=20230923

No need to book in advance, you can buy tickets on site in Santorini

I agree with JoLui. Sounds like a great trip. My only comment is that if you’re planning to go this September, you should begin reserving flights & hotels ASAP. It’s a busy year in Greece.

We did a similar itinerary, swapping Crete for Santorini, in June.

If you use ACR for your Athens car rental, as many on this forum do, I would recommend considering driving into Athens and parking the car at a paid garage near your hotel, having arranged for ACR to collect it from that address.

This saves the 2+ hours of time of an unnecessary drive out to the airport and transport back into Athens.

We drove into Athens at about 7pm. My husband was navigating and a huge help in reading signs and keeping it clear where I needed to go.

It was challenging, but not impossible. If you are confident driving in European cities then you should consider it for the hours you save.

I also should say that , like you, I was concerned that the trip was too complex and I was worried about making all of the connections. But everything came together and we had a great trip. (and I had two pre-teens in tow)

We did what the previous poster suggested and flew Naxos-Athens then drove to Nafplio. This worked well. Only hiccup is that they could not accommodate our rolling carry ons in the cabin of the tiny plane so we had to wait for them at Athens.

I would not want to have only one day in Athens, so would encourage you not to pre-book that Delphi side trip.

I would return the car to the Athens airport and take a taxi to your hotel. Much less stressful.

And I would spend the second day in Athens. There is a lot to see and do in Athens: ancient ruins, amazing museums, the Athens central market, and more.

After Napflion visit Delphi en route back to Athens. Spend a night in the mountains in beautiful Delphi.

Suki, are you asking OP to change her flight tickets in order to have a night in Delphi? She may not have that option or the $$ it would require. Actually, her schedule is tight, and I think that 2.5 days (half of 9/3 plus 10/1-2) is barely time to do justice to the World-famous Landmarks in Athens, plus Acrop. Museum and maybe a glancing blow at the magificent Nat. Arch Museum. I too am a fan of Delphi, but maybe not in this cram-jammed first trip unless there is a classics scholar along, who can explain it adequately. I saw Delphi as a day-trip on my first visit to Greece, unprepared, in a mob-scene bus tour... a nightmare. Ten years later, I went back on my own, D-I-Y, and after Classics courses, books, etc & print-outs. It was wonderful. For others, a licensed guide a help.... it's something to save for trip #2.