Naxos or Paros, and many more agenda dilemmas!

Before we spend time on this complex wish list, can you tell us -- have you already booked international & domestic flights and also any hotels in these destinations? All too often I work hard at tweaking an itinerary, to maximize enjoyment, and minimize travel time, only to have people say, oh I'm locked in to such & such.

Hi Janet,
So far we’ve only booked flights. Arriving on Sept 3 and departing on sept 17. No other transportation yet. Thank you!

I think you are trying to see as much as you possibly can and it’s starting to cram in too much for 2 weeks. Traveling with four people in your group makes going to too many destinations even more problematic.
You have 6 destinations for 14 nights. That’s 2 nights in each one plus two floating nights. Being in Athens the night before your return flight home is mandatory. I would make it three nights in Athens so you have time to see
The Acropolis and the Parthenon, the Acropolis Museum , the Ancient Agora, the Roman Agora, the National Archaeological Museum, the Plaka, The Temple of Olympian Zeus. Give yourself extra time in Athens so you can see these incredible monuments.
Until you’ve seen all that Athens offers, it makes little sense to cut it short to go see other remote sites.
To maximize time, I would ✈️ fly the 1-hr flight to Santorini immediately upon arriving in Athens. After your 3 nights in Santorini, ⛴ ferry 2-2.5 hours to Paros for a few nights. You can then move on to Naxos by ferry or catamaran in 30-60minutes for several nights. I would drop Crete as it’s the outlier and a time sink in relation to transport to the other islands.
Fly back to Athens from Naxos in 40 minutes. You can also ferry back to Piraeus, Athens’ Port, in 3-5 hours but flights are about the same price as ferries if you book them now. Nafplion is about 2 hours by bus or car from Athens. Mycenae is 45 bus minutes from Nafplion on the way back to Athens . Mycenae is interesting as an archaeological site and I recommend it. I also have been to Olympia but-unless your group is obsessed with seeing it- I would drop it. The towns near Olympia are not that interesting and it is 2.5 hours drive or taxi ride from Nafplion. Public transport there will take hours longer.
You can check airfares at Skyscanner.com and boat schedules at Ferryhopper.com
You’ll find when traveling with a group less is truly more.

Have a great Trip!

I would pare down even more. I think four locations for 14 nights is about perfect. I would pick either Paros or Naxos not both. We went in 2018 with a group of 7 and we spent 3 nights in Santorini (flying there upon arrival) 4 nights Naxos, 4 nights Nafplio, and 3 in Athens. I am partial to Naxos because we loved it but I haven’t been to Paros. I am sure you would enjoy whichever you chose.

In my view, Crete is a separate trip. In fact, we are going there in a few weeks!

I'd pare down as well. I'm not going to tell anyone to spend more time in Athens than I did, but I do plan to return. You don't have any time for a day trip to Delphi since you only have a day in Athens, and I would definitely not fly from Crete the day I needed to catch an international flight (too risky!). Plus, traveling with four instead of two means you may need a slightly slower pace.
The drive to Nafplio is easy, but practically you get there and turn back around, so I'd exclude something. More time in fewer places has never been a disappointment to me, but moving around too quickly definitely has.
Please look at drive and travel times carefully and I think you'll find it easy to rework this plan. I don't think it's a tragedy to fly to Crete for four nights, but I would personally save it and explore the whole island on a separate trip, then give more time to your other destinations.
Short answer, just listen to Janet

I also think of Crete as a separate trip— it is huge for an island. It is about the same size as the island of Cyprus which is its own country.

Kenka has taken the time and care to give y ou a do-able itinerary, and Beth and Valdelplhia have further tweaked it to give y ou a better experience. Hold off on crete, save for your next trip (and when you DO get there, do not spend time in Elounda unless you are fond of upscale resorts with no historical or landscape highlights). Choose Naxos or Paros for at least 4 days... and I'd say Naxos, very vibrant in Sept, and as fertile, productive island has vineyards (sometimes September wine festivals in hill village).

Fly from there in the AM & get your rental car & set off for Nafplio.. that way you'll have time to stop at ANCIENT NEMEA -- hidden gem -- a "sacred games site/OLympa runner-up ... look it up! Splendid stadium.. a real thrill... without a 2-day trip to Olympia. DO your homework to get the most from amazing Nafplio - http://www.visitnafplio.com/ is THE best-ever website, read Every LInk!!! (If u don't feel like Mycenae, Tiryns is another fab Iliad-era fortress 5 minute outside of Nafplio; NO crowds, huge boulder-walls).

Get into ATH in the afternoon so u can have 3 FULL Days to sightsee. Either do Acropolis at 8 AM, or 4:30 pm, avoid crowds. If u dont want to be in a tour, go to RICK STEVES Athens website & you can get FREE download audio guides-- step by step DIY, so u can do it on your own; alas downloads for Ancient Agora and "10 top sights" of Nat. Arch Museum. With only 3 days to cover just the Athens Highlight I would not cut it short for a day-trip to Delphi, certainly not as a day bus tour, or unless u have done Classical History. Read up & do it next time.

This itinerary will work; I've done something similar with newcomers half a dozen times & they loved every minute.

Thank you all for the information. I feel a lot more educated in planning for our trip!