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Rough September 2025 Itinerary Review

Posted by (Massachusetts) on

Hello everyone! I've been working on a trip to Greece for September 2025, and I have really appreciated the help and feedback I've received here. I have a rough itinerary and would love your input on any mistakes I’ve made or improvements you would suggest, please. I've started booking hotels, so I'd like to make adjustments sooner rather than later.

Itinerary:

  • 09/07: depart Boston (3:00 PM) 09/08: arrive Athens (7:00 AM), fly to Milos (9:35 AM - 10:15 AM), ferry to Sifnos (time TBD based on schedule), check in at hotel in Apollonia
  • 09/08–09/12: Sifnos (5 nights, 4.5 days)
  • 09/12: ferry to Naxos (time TBD based on schedule), check in at hotel near Naxos Town
  • 09/12–09/17: Naxos (5 nights, 4.5 days)
  • 09/18: fly to Athens (3:25 PM – 4:15 PM), drive/bus to Nafplio, check in at hotel in Old Town
  • 09/18–09/20: Nafplio (3 nights, 2 days)
  • 09/21: drive/bus to Athens, check in at hotel in Athens (where is TBD, still looking for accommodations)
  • 09/21–09/24: Athens (4 nights, 3 days)
  • 09/25: depart Athens (6:00 AM)

As a note, I know that traveling between Sifnos and Naxos is not the best use of time, but I wanted to go to those two islands, and I’m stubborn, so I’m accepting that this may not be ideal.

Please let me know what you think! Here are my current concerns, but I'm all ears for any other feedback.

Concerns:

  1. I understand that driving to Nafplio is longer and more difficult than it seems. Is it foolish to rent a car and drive if my flight arrives in Athens at 4:15 PM? Would it be better to take a bus to Nafplio, rent a car in Nafplio, and drop it off at the Athens Airport - this does add a $130 fee, though. I thought driving might be an adventure, but does that demand more time than I have? Would it be better to take the bus both ways?
  2. Is two days in Nafplio worth it, or should I spend all my time in Athens once I return instead? Alternatively, should I stay longer in Naxos? Although, I've already paid $50 to change my flight once - oops.
  3. I plan to rent cars in Sifnos and Naxos. Is it also worth renting a car in Nafplio for just two days?

I’d appreciate any advice—thank you very much!

Posted by
434 posts

Hi rollingandunrolling. The first note I would make would be to doublecheck your dates before booking hotels. For instance, you have 5 nights each listed for Sifnos and Naxos but the dates you list are actually 4 and 6 nights respectively. As far as the car rental from Athens, we rented a car at the airport and drove to Napflio and found it to be a very easy drive. My husband drove and he normally leaves international driving to me, but had no problem with this route. If I remember correctly, the drive was only about 2 - 2 1/2 hours. Obviously, whether Napflio is "worth it" is subjective. We enjoyed our time there, but also did day trips.

We stayed 4 nights in Naxos and found that to be enough for us, I would have preferred 3, but then I am not much of a beach person so you may feel differently.

Posted by
1494 posts

Well this is a busy plan but you are hitting well recommended places and your sequence of hopping seems doable.

If it were me I would rent the car at Athens airport and drive to Nafplio. The car gives you flexability to site-see on the way to and from Nafplio. You may want to stop at Corinth to see the canal then stop at Ancient Corinth and the fortress at Acrocorinth. That stop can be done coming to Nafplio or returning to Athens.

You might use the car to visit the ancient sites near Nafplio as well.

Posted by
2536 posts

Driving from the airport to Nafplio is not particularly difficult, even easy. Rent a car and you will be in Nafplio around 7:30 pm.
Also, the buses to Nafplio do not leave from the airport but from the bus station of Kifissos in Athens center

Is two days in Nafplio worth it

Yes of course. Especially since you will arrive in Nafplio relatively late on September 18th

I plan to rent cars in Sifnos and Naxos. Is it also worth renting a
car in Nafplio for just two days?

By renting a car at the airport to go to Nafplio and returning it to Athens, the question no longer arises, and as stanbr says you can take the car to visit the sites near Nafplio

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