help with Greece itinerary

I can't answer all your concerns but I can add a few comments.
* I would go to Athens first, and see the sights and have some good and reasonably priced food.
• its about 5 hours on the ferry from Athens to Mykonos, but the time and price varies depending on the ferry company - depending on how long and how many stops at other islands. Prices were about 36-52 eu per person. Santorini is even further. Add to your expenses taxis to and from the airport. In Mykonos we ended up paying 20eu for 3 people to go a few miles to get back to the ferry station - as opposed to a little more than that for 3 people in Athens to go 30 miles away. As mentioned below, every aspect of going to Santorini will likely be expensive.
• research the weather well. We found Mykonos really cold and windy and fairly unpleasant to be outside in November, and related t that, 90% of the shops and restaurants were closed. I don't know what spring is like, but don't assume it's nice.
• Make sure to check prices before making a decision. It seems those islands are super expensive for both hotel and restaurants. The one bit of good news for us was that we only paid $200/night for hotel, for a room that would be $500/night in main season. But $100 for simple lunch for three people (no drinks), and the food was not very good at all, and then they openly ask for tips on top of that. Everything was cleaned up and cutesy, but it was so geared toward rich tourists, that I would never go back there, and I doubt I would go to any other super hyped Greek Island. It reminded me a bit of Capri in Italy, which is way more scenic actually.
• We were going to go to Napflio too but some changes of plan cut down our time. I actually tried to get transport there from Piraeus (Athens port) but got lost, and changed plans. So next time we will research that trip better.
• One friend from Greece recommends Delphi. And another friend who went to Greek raved about Meteora. One Greek lady we were talking to was very proud of Corfu and its mix of cultures. And I have very pleasant memories of Chios where we spent an evening transiting from Turkey to Greece.

Hope that helps a little.

Experienced Greek visitors often recommend you fly to your first island immediately on arrival in Athens. Santorini has several flights a day so finding a flight even in the evening should be available. Spend 2 or 3 nights in Santorini depending on your budget. Then ferry to Naxos. Naxos needs a week, 5 days minimum. It is a great companion island with Santorini. Naxos will give you an authentic Greek experience compared to Santorini.

Make the ferry hop Santorini to Naxos your Ferry experience. Fly from Naxos to Athens and do your exploration of the ancient sites. 2 or 3 days can do the important sites easily. Be sure to be on the mainland the night before your return flight.

While Nafplio is a great destination you simply do not have enough time to do that.

Here is why Naxos needs 5 days
Around Naxos town 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299959098
Back to Naxos 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299940917
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Thanks to you both for your different perspectives -- food for thought! Both approaches Athens first, or last have their very good points. Stanbr, I had seen your Naxos pics as I scoured the travel forum, and was so impressed with the beauty of Naxos and your pictures! I especially loved the wine glass shot-- very, very clever! I agree, the ferry between Naxos and Santorini is the "ferry experience" and will fly between Athens and Santorini. The question is if we can get a direct flight home from Santorini ( via another European city where we can fly direct to Boston) and we can skip flying home from Athens. Once I figure that piece, it will be # of nights in Athens, etc. But I think it's determined Athens, Naxos, Santorini . Whether we can do Napflios as a day trip from Athens or if it's pushing it, I don't know. And is Delphi possible as a day trip from Athens?

TO your last question, no. Not if you want the best experience, not a taunting sample. But if u want to try ---

DELPHI - day bus tours are a nightmare - spend an hour just picking up @ hotels, 3.5 hrs on road (w rest stop) arrive site same time as TEN-TWELVE other busses, rush thru site, then cramjam into museum, then pulled away for a lunch u don't want & a souvenir stop (both for kickbacks?) ... need I go on?? A D-i-y is posible if lu take intercity bus (or car-hire) up to arrive late afternoon, see museum, spend nite, see ancient ruins 8 - 11 AM< then, when tour mobs arrive, leave. Unless well-versed in classics/history, u benefit from use of licensed guide (€60 per hr/2 hr minimum). Town of delphi has several excellent ones, meet u at the site. Also, decide what return bus u want, buy tix in Athens if iti's the last bus... reserved seats/popular times can sell out.

NAFPLIO - DIY trip possible if take KTEL intercity bus (earliest 6:15, next in about 2 hrs?? -- COVID has upended schedules) ... big intercity hiway right by the sea for 2/3 of way, then on local road thru olive groves, citrus orchards, arrive 10:30 - 10:45. Explore Old TOwn, check out swell tiny museum... up to Acronafplia, wander town, sunset at Harbor. Last bus 9:30pm best to buy tix on arrival, seats r reserved & can sell out. Best guide for sites = http://www.visitnafplio.com READ BEFOREHAND - and have on phone for reference during yr vists.

Here is a list of airlines that fly direct to Santorini. Perhaps this will help.
Airlines Destinations
Aegean Airlines Athens
Seasonal: Tel Aviv-Ben Gurion
Alitalia Seasonal: Milan-Linate, Rome-Fiumicino
Austrian Airlines Seasonal: Vienna
Aviolet Seasonal charter: Belgrade
Blu-express Seasonal: Bergamo, Bologna, Rome-Fiumicino
British Airways Seasonal: London-City, London-Heathrow
Brussels Airlines Seasonal: Brussels
Condor Seasonal: Düsseldorf, Frankfurt, Munich, Stuttgart

It would be possible to visit Napflio as a day trip, but I'd recommend spending at least one night, preferably two or three. There is so much do do around there.

Also, I recommend trying to avoid driving at night especially when not driving on the tollroads.

@Janet thank you for the details about a Delphi day trip. Very valuable details.

I have been reading and researching more, as well as hearing from DH what he wants to do, and with your input think this is the plan -- but I'd still love to hear suggestions for tweaking it.
fly Boston to Santorini
2 nights Santorini
ferry to Naxos - 3 nights
fly Naxos to Athens, rent a car from airport and drive to Napflio
3 nights in Napflio - visit various sites and explore around there
Drive to Athens, return car and 3 nights Athens before flying home

My main question right now - is 3 nights Napflio too much? better spend 4 nights in Naxos and 2 in Napflios?

thanks once again for your input!

that question Naxos or Nafplio? is like asking me, which of your 2 children do you love the most? For me, unanswerable! If pressed, I would say 4 nights in Naxos, because it's so big & varied. BTW, I don't like talking about "nights" because it makes it seem like longer in that place... I prefer saying "4 nights/i.e., 3 full days".

If u want to have the view leaving Santorini, you can get it on the 1030 AM fast-ferry standing on rear deck for 20 mins or so deprting caldera, then indoors w windows, to Naxos by noonish. If u take the 3;15 Blue Star (and hustle fast up to the rear deck to snag seats) u can sit on deck most of way... but don't arrive until 5:30. Thus to get 3 full days, do 4 nights. After your Naxos time, in order not to scant Nafplio, grab the earliest available AM flight to ATH(Aegean is 10:30, SKy Express is not til 11:45) -- you could be in your rental car by noon!

Enroute to Nafplio, 15 mi past canal, suggest a quick stop @ ANCIENT NEMEA. Overlooked gem, "ancient Games runner-up" with temple columns, PLUS swell stadium, beautifully excavated & atmospheric. This map - https://tinyurl.com/zekuft9 - shows big intercity highway route clearly. Then just 30 min over local roads to Nafplio. Before dinner, stroll Old Town, enjoy sunset at seafront. Since less time, I suggest using next AM to see the small superb museum, go up cliff elevator (ask your hotel) To the Parapet & towers of Acronafplio.. after lunch, I suggest you skip Mycenae, instead stop at another wonderful (and unvisited) Iliad-era fortress, ANCIENT NEMEA just outside NAfplio -- awesome boulder construction, NO tour busses.

On AM of day 3, leave after breakfast, you can visit ANCIENT EPIDAURUS enroute back to ATH airport without backtracking. How? dont return on biggie highway = instead drive EAST across the "thumb" of the peloponnese (consult this map) to Epidaurus - dont spend much time in ruins, the awesome Theatre is the Main Event... then just drive up the coastal road to ISthmus. You can stop to see the Old BRIdge over Corinth Canal before you rejoin the big intercity higihway. Remember to turn LEFT at ELefsina to get on bypass road straight to airport (see map). Job done! NOTE; you may pick up car @ 12 -- arrange for return no earlier than 2-3. then take taxi or Welcome Pickups car (same flat fare) to Central Athens hotel. -- second NOTE: On way out of NAfplio, if you have a good early start, you could take an hour to drive up Back way for a qick stop at Mighty Palamidi... just for the view and taking some incredible photos!

Just a few thoughts. Both Naxos and Nafplio are worth more time but you do not have that luxury. Your plan seems well balanced and you will see just enough to cause you to start planning your next Greek trip.

If there is a reason to add one day to Naxos it might be one day less expense on the car rental.

I would like to add something to your drive to Nafplio. Most people pull off the highway for a view of the canal. You might want to walk across the viewing bridge to the west side of the canal. There is a path that runs parallel to the canal. There is interesting stuff along that path. There appears to be a machine gun nest not active, views of the canal, an abandoned rail line and rail bridge over the canal and further along you will come to a rocky section f the path where there are scratches in the rock. They are from the keels of boats that had to be dragged across before the canal was built.
As you drive west you will pass ancient Corinth from the biblical time and right next door is Acrocorinth a huge fortress with 360 degree views over the countryside. You can choose to do Corinth area either going to Nafplio or returning to Athens.
In Janets comments she recommended Ancient Nemia twice. It is an excellent site particularly the stadium. I think Janet was referring to Ancient Tiryns which has massive bolder construction. Its just 4 km from Nafplio so an easy stop.

Here are some additional images of what is available in and around Nafplio.
Nafplio https://www.flickr.com/photos/stanbr54/albums/72157632094108982

Corinth Area. https://www.flickr.com/photos/stanbr54/albums/72157711755443483

You are going to have a wonderful time.

You're right Stanbr, I misspoke... the heap of rocks outside of Nafplio was indeed TIryns. For my first visit, I just hopped a bus heading for Argos & told the driver to let me off at Tiryns... it's right ON the road. And I lucked into a major Repair Performance... there had been a rockfall from the highest wall, up on the hill. A crane at the bottom had lifted a boulder the size of a Volkswagen high high in the air, where it hung, swaying. At the high wall, an argument was going on between a construction engineer, and an archeologist. The crane operator was obviously nervous. What a show! Happily, they eventually agreed. When finished at the site, a visitor can get back to Nafplio by going across the street & standing in front of a grocery store, & flagging down the first Nafplio-bound bus.