First Trip to Greece - Looking for Suggestions

The highlights of our trip to Greece, similar number of days, were: Sifnos, Meteora and Athens. Delphi was interesting too but less so, perhaps because it was quite crowded the day we were there. We also spent a couple of days in Milos which, while beautiful was, for us, too touristy and less interesting.

Just curious, are driving to Delphi the same day you arrive Athens? If I remember that was over a 2 hour drive through the mountains just to get there. I’m not quite sure I would want to drive and then walk the site jet lagged. And I loved Hydra and Naxos. Santorini was crowded with tourists but then your itinerary sounds like a check it off and move on so maybe enjoying the places isn’t that important. We all travel differently.

We did the Rick Steves tour of Greece and spent 10 days on our own. My favorite places were Meteora, Santorini, Naxos, Nafplio, Monemvasia and Athens. We also went to the Pelion Peninsula, but you won't have time for that. Greece is an amazing place and anywhere you go will be great.

What is the purpose of this vacation? Is it to check boxes and be able to say “I did it”?

Because with this itinerary you are making the basic mistake of spending too much time driving and almost not enjoying the places where you will spend the night. That being said, if this is your way of discovering a country, why not.. But I can tell you that this is not the right way.

What time does your flight arrive in Athens, and are you sure you want to drive to Delphi after a long flight?
You will have to drive in an unfamiliar environment for approximately 3 hours while being jetlagged. This is not reasonable, and once you get to Delphi I don't think you will have the time or inclination to visit anything.

In my opinion for the Peloponnese part you should remove Delphi, start with Nafplio, spend 2 nights in Nafplio, then Monemvasia 1 night. Then Kardamily and Mani 3 or 4 nights, and finally Olympia 1 night before returning to Athens.

Even with this itinerary I think it's quite busy. (I did it in 9 days/8 nights)

Don't trust travel times estimated by Google Maps or other apps, you will spend a lot of time driving in the mountains on small winding roads. You can add at least 15% to the estimated times (and this without taking the time to stop for a coffee, a drink, lunch, take a break, or enjoy the scenery).

Your itinerary is basically what we did in April 2018, except in reverse (you’re going counter-clockwise, and we went clockwise). We did stay on Hydra, and that was our island visit on that trip. We did spend a night in Monemvasia, and it was a magical place. Saving Athens for the end of the trip worked well.

https://community.ricksteves.com/travel-forum/greece/first-time-to-the-peloponnese-with-2-3-weeks

This is a great thread that you might find helpful. The island of Kythira is suggested for a visit part way through the trip.

I haven’t gone any further into Peloponnese than Nafplio and surrounding area but doing so is something on my “list”. I have been to Delphi and I agree with those discouraging you from driving there after an international trip. I was surprised how difficult the driving was. Nafplio is easier driving than Delphi.

I spent 3 nights in Nafplio. Perhaps I could have cut back to 2 nights. The town has an art museum (when I was there it was closed Monday and Tuesdays), the palamidi Venetian fortress, and an archaeology museum with the Dendra Panapoly. I didn't make time for any of: Kardamyli, Mani Peninsula, or Monemvasia. Are you sure you have time for Santorini or would you like to save it for another trip? Can you revise your itinerary with how many nights you think you will stay in each location, and one or more sights you want to see each day? My tentative suggestion is, maybe sacrifice Santorini, stay on the mainland, and re-write your itinerary with your other stops more pleasantly spaced out.

I know you say you like to see a lot on your first trip but I think you are trying to cram in too much on this trip. We spent 16 nights in Greece in 2022 and we had 4 overnight destinations. I think you will spend too much time traveling and not enough time at your destinations. Our itinerary was:

Santorini - 3 nights
Naxos - 4 nights
Nafplio - 5 nights
Athens - 4 nights

I'm not suggesting you do exactly what we did but I think it helps to get an idea what other people do.

Regarding what island to visit, you should probably read other guidebooks to become more familiar with the Greek islands. I suggest Lonely Planet, Michelin Green Guide, and Rough Guides.

Personally, we loved Santorini! I know people will say it's crowded and touristy but that's for a good reason. Santorini is stunningly beautiful and very unique. If you decide to keep it in your itinerary, I recommend renting a car for a day to drive around and see other parts of the island, such as the Akrotiri archaeological site, red sand beach, black sand beach, etc.

In Nafplio we stayed at the Pension Omorfi Poli, which we loved. It's in the pedestrianized area; we parked our car in the nearby community parking lot. Breakfast buffet, not included, is delicious and eating outside on the patio is a wonderful way to start your day. When you are there, Nafplio will be overflowing with bougainvillea!!!! We spent 5 nights in Nafplio because in addition to seeing the sites in Nafplio and enjoying its beauty, we visited Mystras (Byzantine ruins; my favorite), Epidaurus, Mycenae, and drove down the Argolid Peninsula exploring some villages. And spent an afternoon at the beach in Nafplio. We saw the most amazing sunset (and the best sunset of our trip) in Nafplio.

I would slow down a bit and try to avoid changing hotels so much. If you can afford it, I'd prioritize islands over the Peloponnese. Something like:
3 nights Santorini
3 nights another island
3 nights Nafphlio
1 nights Delphi
4 nights Athens

I agree with the statement that Santorini is busy because it's incredible. Stay a few nights (we stayed outside of Oia) to see it at different times and have unusual experiences. A cruise around the island and over the caldera was magical!

Oh our hotel in Nafphlio was simple with no views. It was fine; I loved saving money there and would prioritize something nicer in Athens. (our Athens hotel was twice the price yet awful!)

I like your itinerary except for Santorini. Since this your first trip to Greece, go see Santorini but know it isn’t typical of Greek Islands and visit a better island on your next trip to Greece( Naxos.)
You give plenty of quality travel time to the Peloponnese Peninsula which is full of important antiquities.