We've visited Europe a lot, and are only now planning our first trip to Greece. We will have 14 nights, and will already be in Europe, so no jet lag. I welcome feedback on the itinerary generally and the number of nights at each location; me and my spouse are working with our quirks (fear of heights for me; fear of boats for him) and my interest in ancient Greece, in situ or museums, and our joint interest in mosaics. Neither of us are beachy people, though we love good sunset views. We would like to avoid one-night stays. Also, after my first very ambitious plan that seemed to visit every ancient Greek site, I decided we didn't have enough variety in the locations we were visiting.

So, initial thoughts: fly into Thessaloniki, spend three nights. Fly from there to Heraklion, Crete, for three nights. Fly to the Athens airport, pick up a rental car and drive to Naplion for three nights. Then drive to Athens (could visit Temple of Poseidon on the way), spend five nights in Athens. My thought is to have a guide take us to Delphi from Athens as a day trip, in their car. That would be the easiest way for me to get there without having a panic attack, and I really want to visit Delphi because it's such an important site. We've actually already booked the Athens hotel, and it's not available for other dates at this point. Yes, we could find somewhere else to stay but it seems hotel prices have already increased since we initially booked.

I know this doesn't include a lot of places that many people go (for example, Meteora, which I don't think I can handle, and I was willing to not visit Delos on this trip), but it seems to fit our interests. And we can always return, right?

I have read many trip reports on Fodors, so I appreciate all of the helpful information in all of those!

Whatever you choose, I’m sure you’ll have a wonderful trip!

Some comments:

Three nights is not much for Crete. If your only interest there is in Phaistos, three nights in Heraklion could be enough. But OMG, there’s so much else to see there! Maybe defer Crete for a time you can do it justice? Just a thought….

Three nights in Nafplio might not be enough to see all the surrounding sights unless you plan carefully to see sites on the day you arrive and the day you leave AND pack your days quite fully. Maybe it will work for you, but be sure to think through your priorities….l

I’m sure you realize that the Temple of Poseidon is east of Athens, while Nafplio is to the west. With so much to see, I would think you’d need to give the Temple of Poseidon a very high priority to fit it in. It is magnificent, though – your trip, your call.

I see your explanation for using a guide to go to Delphi, but FWIW, I must say how glad I was to see that site with more time than a day trip would allow. It is awesome, IMO, so well worth getting there no matter how you do it. Of course, going to Delphi as a day trip limits your time in Athens, but maybe you’ll still find the time sufficient, and in any case, Athens is among the easiest cities to reach in Greece, so if you have to shortchange it, you might be able to make up the time on a later trip.

Before finalizing your plans, I’d urge you to remember the lesson of the sunk cost fallacy. Changes to your plan for Athens might not be the worst thing you could consider!

You can’t see all of Greece’s many highlights in a single 14-night trip – as you know, you have to make difficult choices that only you can make. Whether you can always return … well, I think that’s up to circumstances no Fodorite can control.

If you haven’t already seen it, here’s the link to my trip report:
With Gratitude for a Glorious Solo Month in Greece

I think your plan isn’t bad but I would skip Crete. Crete is wonderful but it’s a long way for such a short stay and being constantly taking flights doesn’t sound like much fun. You could easily spend your whole holiday - and more - in Crete. There are many possible alternatives but the obvious one is the Peloponnese. The other comment I would make is that your whole itinerary is in cities and we think the best of Greece is its natural environment.

Thank you both for your comments. Kja, your experience in Thessaloniki is what encouraged me to look more into that city. And in terms of the natural environment, that's a good point. Part of the decision-making there is that Greece, from what I've seen, is rather mountainous, even in the Peloponnese, and I'm trying to avoid too much mountain driving. Also, the other part of our trip, before Greece is in more countryside areas, and we live in the Rockies (yes, I know, mountains, but I am familiar with driving in these mountains), so we've more inclined to spend our vacations in the cities (though always some time in the ciountryside).

If we were to add time in the Peloponnese, which specific areas would you suggest?

For more time in the Peloponnese, you might look at Mystras. Definitely worth the better part of a day, IMO!

If you're skipping Meteora because you want to avoid mountains, well, the area leading to those unworldly peaks is mostly flat. The access road to the monasteries is a gently sloping one. Look at google maps to see the route.

It's nice to know that my experiences in Thessaloniki inspired your trip planning -- I thought it a much underrated city!

So many options!

Thanks; Mystras is on my long list of possibilities, I'll look at that again. And thanks for the description of the route to Meteora. Though in terms my interests, it appeals to me less than other places. Yes, so many options - that's always the case when planning travel!

There's absolutely nothing wrong with focusing on cities if that's your preference. And you are absolutely right that mainland Greece can be mountainous - but the main roads seemed to us to be very good (although we took the buses rather than driving ourselves).

One of the things I like about your original plan is spending at least 3 nights in each place. Mystras is both interesting and beautiful but most people wouldn't spend more than a night or two there unless they enjoy hiking as well. You could combine with Monemvasia (and maybe somewhere in the Mani) or one of the small towns along the coast either side of Kalamata. If you have a fascination with antiquity you may enjoy the archaelogical site at Messene (we are yet to visit as it's hard to get to without private transport).

Another alternative would be to do a mini road trip from Nafplio with some combination of visiting Dimitsana, Kalavryta, Nafpaktos, Galaxidi to Delphi and back to Athens. You may not have time for all of these but you get the idea. Be aware though that this is hilly country.

A third alternative would be to drive from Thessaloniki southwards to Nafplio, using those three days to explore along the way (or simply in the region around Thessaloniki). Even if you don't loiter along the way, I'd take the train to Athens and then the bus to Nafplio rather than flying. If you don't want to bother with the transfer between the train station and the bus station, you could take a taxi.

btw, don't feel too bad about missing Meteora. Yes, it's amazing (not least when you imagine why monks built there in the first place) but it's also become a real tourist circus. Visitor numbers, in my opinion, are becoming difficult to manage without detracting from the monasteries.

Lastly, if there is a chance that you'll be back, keep that in mind with your planning.

I’m not a Mykonos fan, but have been there twice, mostly to see Delos with its wonderful mosaics. If you decide to skip Crete, perhaps you could spend some time in the Cyclades where Mykonos/Delos is located. If the tour boats are still running in October you could visit Delos from Paros or Naxos. If not, in October Mykonos doesn’t get the crowds that plague the island in summer. Of course that would involve boats, which you will avoid by your plan of flying to and from Crete.

The Peloponnese has much to offer, and you could avoid both boats and flights if you choose to drive there from Athens. Apart from Nafplio and Mystras, which have already been mentioned, consider the area around Kalamata at the south of the Peloponnese. Near that city is the wonderful Ancient Messene, a huge well restored site, which gets few visitors compared with those in Athens and around Nafplio. It would go well with a visit to Mystras. There are picturesque seaside villages in the south of the Peloponnese which you can reach without taking a boat.