Advice on Itinerary for first timer - islands and Peloponnese

I can only speak to the Peloponnese portion. Let me assure you, the driving is easy--absolutely no worries. The main highway across the Peloponnese is modern, the rest is rural driving.
It's so hard to offer advice on plans like these since so much comes down to personal preference, and you chose these places for a reason, but here's my 2c. Consider staying in Nafplio July 11-14. The town is pleasant, and there is so much to see within that area. You can see Corinth/ArcoCorinth en route to Athens, ditto Nemea (which many say is superior to Olympia), and close to Nafplio, you have Epidaurus and Mycene. There are some other great sites at slightly longer drive times (Mystras is one I would make the drive for). The Bradt Guide to the Peloponnese is a detail-packed guidebook.
I would find that a much more relaxing pace but with still tons to do--bonus points for giving you time to enjoy Nafplio, while spending less time driving.
I would save Delphi for next time.
Sounds like an amazing trip--I can't wait to return to Greece.

Sorry for this question but you say you are going to see your son who is in Paros, and I don't see Paros in your schedule.
Will you meet him in Naxos?

Thanks for replies - I would definitely like to not move hotels as much - maybe we should drop Olympia ? the boys are very interested in Delphi so we need to keep that. Thanks for info on guidebook - I did not know that name and I love guidebooks. And yes, my son will be off Paros in Athens by the time we arrive. I figured he would be tired of Paros but by being in Naxos if they were things he wanted to show us it wouldn’t be hard to go there.

A vote to keep Olympia , which was one of the highlights of our last trip. The Olympic grounds are fascinating and the museum is excellent. Much, much more than simply a sporting g event, Olympia was a spiritual place basic to Greek society. Everything is well--described in English and brings Ancient Greece to life. Highly recommend the Hotel Olympia, just outside the town -lovely rooms, great breakfast, beautiful pool and dinner in olive grove. Wherever you go, enjoy!!

I have not been to Olympia so cannot compare but we went to Nemea which was also the site of ancient Panhellenic games. It is day trip distance from Nafplio. There was a rotation of sites and Nemea was in that rotation. There is a track like at Olympia, temples, and a lovely air conditioned museum which we very much enjoyed both for its content and coolness! It was very hot when we were there in early June.

It would be a nice alternative that would allow for less moving around.

If you are looking for an extra day for Delphi, there used to be a day trip ferry from Naxos to Mykonos, where you could take the trip to Delos — which is highly recommended. I am not sure if it still runs — hopefully someone here will know.

If so, add a night to Naxos to allow for this day trip, and add the other night to your Peloponnese timetable.

So many places to see, so little time! That's always the problem with trip planning.
I'll throw another wrench in by saying if you do keep Olympia, try to fit in Messene, but they are two hours apart.
Just a thought, but another way to possibly adjust the pace might be to keep Delphi and Olympia but skip Nafplio and stay longer on the west side.

IF you are driving from Piraeus to Nafplio, you can get your "Sacred Games" fix on the way, as mentioned, at ANCIENT NEMEA. Here's a Map of Peloponnese that shows the modern highway all the way from Greater Athens almost alla the way to Nafpllio, and then all of the routes around the Pelops: https://tinyurl.com/zekuft9 (click & it gets huuuge; use side-sliides to navigate). Just beyond the Corinth Canal, exit about 5 miles to this amazing well-excavated ancient site with a stunning stadium... has a hero's tunnel, and starting-blocks 2,400 years old for races (!). In fact there is now a Revived NEmean Games http://nemeangames.org/ every 4 years attracting thousands world-wide, it will be on June 22-24, just before your trip, so its observance wind-up may still be going on.

About driving in the Peloponnese, no worries... if you skip Olympia, (look at the map!! It's waaay on the other side of the peninsula, for the short time you've allocated for this part of your trip) you'll have time to explore SO Much more ... the main roads are modern intercity routes, and the local roads in the Argolid region are easy rolling countryside. Forget "George's Taxi" -- George does not exist any more this is just an over-promoted fleet of vehicles.

Another comment on your itinerary -- in terms of transport efficiency, and also maxxing enjoyment... do NOT waste precious hours going in/out of Central Athens checking in/out of hotel there, while still too jet-lagged to sightsee. What we usually advise is to pick up luggage at bag claim & board soonest-availble island flight -- much more fun to recover on a beach! However, I isee that only fligiht left isi at 18:45 (6:45 pm Sky Express), which isi a long time to hang out in airport. Therefore I say, stick with AM flight on on July 5 -- but on the 4th, take FREE Shuttle to HOTel AVRA, 25 mins away, on a nice BEACH in the little port of Rafina... have your first greek swim, and a great nap, and an early dinner under village trees. FREE Shuttle back early next AM For Naxos flight -- Aegean Air still has seats on its 9:30 flight and for the next day or so, is offering % off on all direct domestic flights.

So many choices! I suppose the good news is that it will all be enjoyable. How about this modification - I was on the fence about seeing Santorini- could fly into Athens and then to Santorini since I read there are more flights and then go to Naxos the next day? I also could add a day I think and start July 3. Is Santorini just too crowded to enjoy though? I also thought of seeing about doing the Peloponnese portion with Eudamonia tours but they may be out of my price range.

In my opinion, you are too greedy in destinations.

Only for the islands, If you add Santorini to your trip you will go to Santorini+Naxos+Mykonos in 4 or 5 days.
This is not reasonnable.

You will spend your time packing and unpacking, transferring between accommodation and ports or airports, waiting for a plane or a ferry, driving a car, etc. etc.

You say you like hiking, snorkeling, sailing... When will you have time to do this?
You will not enjoy the places where you are.

The Greeks are the inventors of the marathon, but that's no reason to want to surpass Phidippides :)

You do have alternatives, if, as the previous writer said, be less greedy, and perhaps drop an island. Here's my thouht:

•JULY 4 - Arr 11:45 am & transfer to flight to SANTORINI. 2 hrs in between usually enough - AEGEAN AiR 13:30 (1:30pm) may be too tight time-frame in busy high season; next AEGEAN Is 1500 (3 pm). https://www.skyexpress.gr/en just as good, has 14:00 (2pm) -- grab it! (Remember, lowest rate = no luggage, take fare that allows 1 big bag. -- Arrive 3 pm ... time to explore rim path, find place (NOT in OIA) For sunset dining. Then crash, to get over jet lag. I advise find cliffside hotel in FIROSTEPHANI because those mobs don't come there... and it's walkable to FIRA town, no need for taxii.
• JULY 5 - Up by 7:30 (YES even the teen!) taxi 8:15 to OIA To enjoy scenery take photos while it's still walkable. @ 9:30-10:00, the mob scene! Invasion by cruise crowds, package-tour busses, narrow lanes jampacked. Grab BUS back to FIRA town & go somewher less crowded --- I recommend taxi to ANCIENT FIRA (Hi bluff with ruins overlooking east beaches) -- afterward u can do quick swim if burny-hot but Beware! BLack lava beach burns feet! Evening? those with pep can walk to FIRA nightlife.
• JULY 6 -- take 3:15 BLUE STAR Ferry to NAXOS Arr 5:30. Get econmy tickets (no reserve seats); Get to pier bldg by 2;30 to be near head of line, have sons rush upstairs to back deck to snag 4 seats... then enjoy 2 -hr mini-cruise.
• JULY 6-7-8-9 -- NAXOS. Do NOT move on to MYKONOS -- if your reason is DELOS, you can take day-excursion MV ALEXANDER which giies you 2 hrs on Delos, and 2 hrs on Mykonos as a sample, without the cruisie-crowd crush & $$$
•  JULY !0 - FLY BACK To ATH (You don't have time for 6+ hr ferry) SKY EXPRESS 8:55 - 940 .. pick up rental car drive to NAFPLIO (do ANCIENT NEMEA On the Way!) Afternoon exploring Old TOwn Overnight in Nafplio (old town if possible, or nearby beach)
• JULY 11 & 12 - NAFPLIO & famous ancient sites (EPIDAURUS-TIRYNS) & Palaimid -- remember it will be HOT HOT HOT ... a good routine is AM for Sites, AFternoon for SWIMS.
• JULY 13 -- To oDelplhi & ovenight
• JULY 14 - 15 16 17 - ATHENS ... Do NOT Stay at Grand HYATT... Booking dot com lisits tons of priivate apts. available in good area to E & S of Acropolls where u can have 2 br & balcony for way less than Big Convention hotel. For browsing, I like to use thisi filter of Booking - https://tinyurl.com/heq6edp --which focusses on Hotels closest to Acropolis. When u put in dates & numbers (4 people/2rooms) you get a long list but instead click on RH corner "Show on map" & see blue "balloons" of all availablel places. Touch a balloon for price & name.. click for details. Better than VRBO or AIrBnB, more safeguards & free cancellaions.

Janet always has great advice. I can only give you my advice on the Peloponnese, Athens, & Delphi. In July, it will be very hot and probably humid. Make sure your lodging has a/c, which I think most do.

Old town Athens if you can get a place to stay is your best bet. We stayed at the marvelous hotel The Zillers, which is likely booked up by now. Make sure you out of your lodging and with whatever tour group (if you wish), at the gate by 8:30, or whenever it opens. You can see the Agora, but I'd see this on a separate day, as it will make your day long to add this to the Acropolis. I'd also recommend Athen Walking Tours. We used them for the Acropolis & a food tour. We had Irini as our guide and she was delightful.

Drive times between cities can be longer or about the same as the estimates. Driving to Delphi is like driving highway 1 on the California coast, so maybe a day trip with a driver. Driving is easy outside of Athens except for the aggressive passing on blind curves Greeks. They admit they are impatient. We used Georgia Hoelkis as our guide which made our arrangements easier. There's also no shade at the archaeological sites, really. Buy your tickets online for any of the sites as ticket lines will be long. Wear a hat.
Driving from Delphi with a stop will take you closer to 4 hours because of traffic, I think, plus there's ongoing construction on the bridge from the north on the way to Olympia.

I do think you're trying to get far too much out of your trip, and believe me I understand. We'll have been here 2 weeks on the 20th (the day we leave) and you will be burned out by the time you leave. Someone suggested Mycene to visit. I would skip that because it may be interesting for your son, but it can be a challenge when the GPS takes you through backroads that you don't need to tackle.

BTW, we went to Meteora instead of the islands and stayed there 2 nights and it was so worth it. Not that you're going there, just perspective as to how many days you're planning for the islands with the Peloponnese in your 2 week schedule. Just know you'll be tired. We had no trouble with jet lag, even with 1 night layover at JFK.

Sue and Janet -
Thank you so much for all the detailed advice. It is so hard not to be over ambitious, but it is nice when you don’t have to recover from your vacation.

Janet, we are planning to do your modifications to my suggested itinerary. You are correct we have no interest in Mykonos - only for Delos, so if we can book the trip to there from Naxos that would be better. I do see sometimes the seas are rough in July though?

My current quest is to secure someplace in Athens July 14-18 as places are going fast it seems. Ideal budget under $200 per night - I think apartment is probably a good idea to have a little more space and be able to eat breakfast in. I have come up with there on Airbnb - if anyone has time and wants to give opinions on location It would be great. Working in booking dot com too. After this will be all the other lodgings and tickets!
https://www.airbnb.com/wishlists/v/1083925077?s=42

Macker glad u like my suggestions but one BIG CHange -- Do air tickets FIRST!! ! You can always find anoher room or apt, even if not perfect, what you can't find is another airplane. If u can't get a flight it screws up the entire plan Stop now with lodging choices -- book Air NOW>

I know -
working on flights but it is complicated because one has to be done through work portal and one will be there on a different ticket. Regardless because of work I know we will be in Athens those days so I decided to work on something I could do this weekend.

I wanted to add that back in 2011 my daughter and I took the day trip boat from Naxos to Delos and Mykonos. It was a great trip and I highly recommend it. Full disclosure---we were fine, but it was a windy day and a few of the passengers got seasick.

In 2018, we took a Viator tour to the Peloponnese and I can also highly recommend that. It was a large bus, but the guide was wonderful and there was a wide variety of folks on the tour--- all different ages, some families with college age like us. The disadvantage of the tour we took is we only stopped at Nafplio to stretch our legs, but we saw Olympia, Delphi, Meteora, Corinth, and Epidaurus (not in that order!). I think it was 3 nights/4 days for about $600 each.
The order of your trip is smart because you will be on the islands the first days when you have jet leg. There was one college age traveler on the tour who slept much of the time on the bus, trying to get over her jet leg. Which was too bad, because the scenery was wonderful. ( She and her aunts were heading on to the islands after the Peloponnese. ) Which was too bad, because the scenery was wonderful.

A PS to Brenda's useful comments ... there are TWO excursion boats that (in normal times) do the day trip to MYkonos... Naxos Star (small, bumpy when affected by wind) and MV Alexander (larger, thus smoother ride). I'm guessing Brenda had the first. HM Alexander doesn't go as often I think/ As soon as you arrive on Naxos, check with any ticket agency to find schedules. ALSO, if you have re which day for your excursion, the day BEFORE, check the weather forecast, before you book the trip. In calm weather, either is OK.

As an independent traveler, I abhore bus tours. It might be right for you. 2 comments on your choices of your stay in Athens. The one that is $234/night is about where we stayed and is a wonderful view of the the acropolis and the area is nice. The Plakka is close and not too close. The one that caught my eye is the Parthenon dream because of the free parking. That would be ideal if you have a car in Athens, although I wouldn't recommend it. We used Bazaar rental car agency for a rental car because they drive you to the edge of town and say bye bye. The car is little and gets us around just fine. If you have no car in Athens, I'd recommend the one for $234/night. The location is perfect.