3 week Greece itinerary in May

Posted by vaneliunas on 12/29/25 12:55 AM

Hello - I've read several of the Q&A in this forum in my attempt to generate an itinerary, but would love to get some additional help. We will be a family of 4 (youngest age 19) travelling the first 3 weeks of May. One of my daughters is more interested in the islands over mainland and may have to go home early for work, so I'm planning for the islands at the beginning of the trip. I know that many of you have suggested leaving Athens for the end since ferries can be unreliable, but since we will be on the mainland the latter portion of the trip and my daughter would like to see Athens, I have it at the beginning. Here's what I have planned so far:

Monday, May 4: Land in Athens (3 nights Athens).
Thursday, May 7: Fly or ferry to Santorini (3 nights Santorini).
Sunday, May 10: Ferry to Naxos (5 nights Naxos).
Friday, May 15: Ferry or fly to Athens (if my daughter has to leave early, she will fly home from Naxos that morning).
Friday, May 15: Rent a car in Athens and drive to Nafplio (see Corinth dam on the way). (4 nights Nafplio).
NEED TO FILL THIS IN!
Sunday, May 24: Fly home from Athens (12:45 pm flight departure).

Questions:
1) I'm torn about whether I should keep this first half as is (3 nights Athens, 3 nights Santorini, 5 nights Naxos), or if I should do 4 nights Athens, 3 nights Santorini, 4 nights Naxos?
2) If we check out of Nafplio accommodation on Tuesday, May 19 and have 5 remaining nights before our departure, how should we spend it? I'm thinking we will spend our last night in Athens, so that would be 4 nights elsewhere. Please feel free to suggest a different itinerary (ie. somewhere else before Nafplio), but the islands must remain at the beginning of the itinerary.
3) If we wanted to rent a car on Naxos, should this be arranged in advance to get best rate? Any particular location to get the car rental from (ie. airport vs ferry terminal)?
4) Similarly, for car rental in Athens, where would be the best to rent from? I'm not sure whether we will be flying or taking the ferry - I assume that if we fly, airport car rental would be best. However, we will likely ferry - where would be the best location to rent from?
5) My daughter would very much like to do a boat or catamaran excursion and my thought is that a sunset cruise in Santorini would be nice. However, I think she would also like an excursion that would lead to a beautiful beach with clear, calm water for swimming. If anyone has a suggestion for this type of excursion from Santorini or Naxos please share.

Thank you all, and please feel free to comment on anything I haven't specifically asked about!

Posted by JoLui

France Southwest

12/29/25 11:20 AM

3363 posts

1/ You can keep your original plan with the 5 nights in Naxos. But it all depends on what you intend to do there. If you rent a car, you'll have plenty to keep you busy for 4 days (I spent a total of 15 days in Naxos and I didn't see everything).

2/ It's always difficult to recommend places to visit in the Peloponnese. Especially since in 4 days you'll have to make some choices.
The best thing would be for you to do some research and see what interests you. Don't try to see too much, travel times in the Peloponnese are much longer than you might think from looking at Google Maps.

Another option would be to dedicate these 4 days to visiting Meteora and Delphi. It's up to you.

3/ On the Greek islands, I always rent from local car rental companies. I don't have any particular preferences except that I prefer rental companies that don't require prepayment through an online booking system.

Try Google Maps, center the view, and zoom in on Naxos Town (where the port is) and search for "Rent a Car".

Then you just have to choose based on rates, car types, reviews, etc.

The vast majority of rental companies can arrange a pick-up and drop-off of the car wherever you want, whether it's the airport, the port, or sometimes even your hotel. Sometimes all it takes is sending an email asking about prices and availability. No formalities are needed; you can often pay in cash when you pick up the car, this is quite common in Greece.

4/ Same principle as for Naxos. If you want to rent a car at the port of Piraeus, zoom in on the port with Google Maps and search for "Rent a Car".

If you're returning to Athens by ferry and want to head straight to Nafplio, the best option is to rent a car at the port of Piraeus.
From the port of Piraeus, the airport is in the opposite direction from Nafplio and about an hour away. Renting a car at the airport adds at least 2 hours to your trip to Nafplio.

Alternatively, in Athens, all the car rental companies are located on Siggrou Avenue in the city center. Some have an office at the airport. I sometimes rent cars from Athens, either in the city or at the airport, using the same principle: no prepayment through an online booking system. This provides some flexibility for last-minute cancellations.

Siggrou Avenue is located here:

https://maps.app.goo.gl/yEV5KeTKjX2mvXEf7

5/ In Naxos you will find all kinds of excursion and daytrips options at local travel agencies. You can take a look in advance at some travel agencies that have websites. One agency established for years in Naxos is Zas Tour, but you'll find others there. They have signs in front of their shops showing the tours they offer.

Since boat trips depend mainly on the weather, there is no point in booking in advance without knowing what the weather is going to be like.

https://zastours.com/naxos