Itinerary rough draft

If your days are flexible, why not fly home the day/day after your mom cruises? Why not end the trip with your mom activities?

I think this would work better if you rented car when you returned from islands and mom and boyfriend arrived (and I would fly to simplify things) and then all went to Nafplio. It takes an hour to get from airport to center of Athens so doing it twice is inefficient.

You then would see Athens after they go on their cruise and they after they return from cruise.

I thought with jet lag it would be best to go straight to the islands. My moms cruise does the islands so she wouldn’t want to do that and so I figured we would do land stuff that she probably wouldn’t do without me planning/doing it. But if we fly in/leave a week later then it seems there is “wasted” time unless I figured it wrong.

We could totally go straight to Naplio etc when my Mom gets in, I just thought they might be tired…

As a precaution, I would stay one night less in Santorini (or another island) in order to return to Athens one day before your mother's arrival.

Actually I think you have thought this out pretty well.
Your choice to fly immediately to Santorini on arrival in Athens is a good one. Getting over jet lag on an island is way better than in Athens. I appreciate how tired you are going to be because we live about a hundred miles due north of you. Its a long haul. Waking up in Santorini will go a long way to taking care of jet lag.

I would split my island days 2 for Santorini (very expensive) and the other 4 on Naxos. Excellent choice. The Santorini Naxos combination is a great one. Naxos will give you an authentic Greek experience.

Fly back to Athens from Naxos pick up Mom at the airport, rent a car and scoot to Nafplio. I know Mom will be jet lagged but you will be driving so no problem. Nafplio is very much like an island experience as it is directly on the sea. Nafplio will give Mom a good opportunity to relax and get into Greek mode.
Athens last will give you time to adjust to the Greek way of doing things and you will be ready to explore the city.

For fun this is Naxos and Nafplio
Naxos town https://www.flickr.com/photos/stanbr54/albums/72157632094558042
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481
Nafplio https://www.flickr.com/photos/stanbr54/albums/72157632094108982

You have all been so helpful, thank you!
I have taken out the night stay in Athens on my Mom's arrival and go straight to Napflio.
I am unsure about renting a car...I cannot drive and my boyfriend, I think, would have anxiety with the way people drive over there. Unless it is an easy drive, then there wouldn't be a problem. What do you think we should do? I have been to Italy and the way people drove over there was crazy!

I drove from Athens airport to Nafplio and in surrounding areas. I did not find the driving difficult. My brother in law who had driven to Delphi had warned me about driving in Greece but we didn’t find it anything like that.

There were two challenges though.

1. Signs are all in English (as well as Greek) but only once before necessary exit in contrast to US where signs are there multiple times. So someone needs to be paying attention.
2. The exit we needed for nafplio was not marked for nafplio but some other city that I don’t remember now. We initially took the wrong exit.

To avoid adventures, I would get a map of Greece ahead of time (can order on Amazon) and/or download goggle maps on your phone. I had expected a map from rental car place like in US and was not as prepared as I should have been. We are going back to Greece in a few weeks and I have maps this time!!

Beth

About car rental & driving hesitancy --- IF you rent the car from the AIRPORT, it becomes Easy & SAfe. check out this online map - https://tinyurl.com/zekuft9 --(click & it gets huuuge, and you navigate using side-slides) IT shows the road all the way from Airport to Nafplio. As u can see it's a modern "beltway" skirting Athens,... it's a multilane divided highway all the way past Corinth Canal. And when u turn SOUTH To Nafplio, the local road is 2-lane but at time you are traveling, low traffic, very enjoyable... it goes through olive groves and citrus orchards.

Beth is right about one thing - Greek highway engineers do not cater to American ADHD tendencies... you have to stay focussed to spot the sign you need. Its not lie US, where our highway signs say "exit 42, 1 mile," "exit 42, 1/2 mile," "exit 42, 1/4 mile" "exit 42, 1000yards" . I Greece there's a sign in GREEK saying ΆΡΓΟΣ (Argos) and then, about 100 yards onward, there's a BROWN sign with yellow lettering that says in English "ARGOS" and then BAM!! there's the turn-off. So don't daydream & you'll be fine. ALso, if you don't have a paper map, inform your rental company ahead of time that you'll expect one. They all have them ... they've just gotten lazy about handing them out , with the advent of gps. Also, at your hotel, use your map and ask your hotel people about best way to get to such & such, & have them mark map. They may well tell you about special things in addition.

If you follow my suggestions you will be picking up the car at the airport. That means you will be on a major 4 lane highway (tolls) all the way to Corinth. You do not have to drive in crazy Athens. Just keep over to the right and let fast cars pass. If you have a GPS that would be good. Even with a GPS its a good idea to buy a map so you can follow along where you are going. The drive south from Corinth is on a two lane highway that meanders through wine country. Its a lovely drive. Locals will stack up behind you because they drive fast. don't worry about them they will pass as soon as they can.

The driver needs to concentrate on driving and the other passenger needs to navigate.

The car rental is by far the best option to get to Nafplio and to explore the surrounding antiquities.

Wonderful! Thank you all for being so helpful! I am narrowing down more details now for the area and will probably look for more opinions later on about that. Thanks again :)

Janet and Beth, I appreciate your detailed advice/instructions about driving in Greece. We are leaving for Greece on May 12. I planned my trip with the help of Janet and some other posters on the Fodors forum. I will definitely order a map of Greece from Amazon.

Vintagelove, I have planned almost the exact same itinerary as you, but without the logistics of planning around someone else's itinerary as well. We are going to Santorini first (3 nights); then will take the Blue Star Ferry to Naxos (4 nights); we have airline reservations to fly from Naxos to Athens Airport where we will pick up a rental car and drive to Nafplion (5 nights); then return the car to Athens airport and spend our last 4 nights in Athens. So, even though we haven't left yet, I am confident I have an awesome trip planned, and I am sure your trip will be awesome, too!

I am glad to get the credit from K Woo, whom I led along, through a series fo discussions, on another forum. Her trip sounds very well pllanned by now... and I personallly can vouch for its workability, because I've done it more than once! with aa few newcomers. Will pass along what I've said to anyone planning such a trip: (1) Transport arrangements FIRST... do not get locked-into a hotel becaue you fell in love with the photos of bed linens! FIRST make sure you can get TO A destination & onward to the next ... you can always find another hotel --- if the last flight of hte day is full, you can't magically find another airplane (2) For hotels, LOCATION is more important than decor (3) Do Athens LAst. and (4) Listen to everything Stanbr says .... his advice is GOLD.