We are two couples planning a trip in mid September for about 3 weeks. Nothing is booked and we are open to ideas and suggestions. We are looking for beautiful towns, good food, and exploring with short hikes. We are not into nightlife and big crowds. Our thoughts are to divide the trip into 3 parts. Islands: maybe Naxos 4 nights, Milos 3 nights. Peloponnese: Napflio 4 nights , Limeni 3 nights (Mani coast), and then Meteora: 2 nights stopping in Delphi and ending in Athens. I am looking how to best arrange this and the best way to travel. Meteora is definitely a long drive but a bucket list item. We are comfortable driving and have done it on many European vacations. In what order would make the most sense? I have looked at Greece so many times but always get overwhelmed with the planning, but this time we are going! I would love some suggestions. Thank you.
Yours is easier than most! Fly to islands on arrival (someone else can advise on that part). On return to ATH, pick up car and return it when you return to Athens.
I'd play around with the driving times and such for doing Meteora first or the Peloponnese first--try all iterations for the order to see what works best for you. I found Google maps fairly reliable.
FYI :
Naxos is in the Central Cyclades, Milos is in the Western Cyclades.
The only ferries that connect these two islands are the ones that have a tortuous intracycladic route in high season.
- The two fast catamarans Superjet 1 and SuperJet 2 from Seajets follows this route (departure 15:15, arrival 20:00):
Naxos → Paros → Mykonos → Paros → Sifnos → Milos
It's a 5h ride in very uncomfortable ferries where you are stuck in your seat like in an airplane cabin.
There is also a conventional ferry once a week that operates between Naxos and Milos;
Naxos → Ios → Sikinos → Folegandros → Kimolos → Milos
The journey Naxos - Milos is more than 6 hours and you arrive around midnight in Milos
I think the reason you are having some trouble is the distances you are trying to cover are a lot.
If you start with the islands, then go to Napflio and then Limeni, it is a 8 hour drive to Meteora. And you want to see Delphi too.
What about this? Napflio 4 nights, Limeni 3 nights, substitute island of Kythira for Naxos and Milos which is off the coast of Peloponnese and can reached by ferry 5 nights, (probably would need one night nearby to catch ferry there), then one night Delphi, and two nights Meteora.
This would take 8 island nights you have and give you 5 on island of Kythira, 1 to catch ferry (different options nearby), and 1 to stay in Delphi (which would be very difficult to do otherwise on way to Meteora).
Or if you prefer Naxos, go to Naxos but spend five nights (skipping Milos), add a night to Peloponnese and a night to Delphi.