Itinerary Help Please

I found Greece very hard to plan for because there is SO MUCH you could see, so it was hard to choose. We were there for 28 days and it was nowhere near enough.

It looks like, from what you describe, you will fly to Athens and then continue directly on flying to Chania? If you have those 5-6 days plotted out, then thats a reasonable time there. IME Crete required a lot of driving. We chose to move around a little ore than you (we spent 3 nights in Chania and then moved to another spot) to try to mitigate the driving. You can see Knossos and the Natural history museum in one long day. We did. I would have liked another day in Heraklion (we spent one day and one night) so depending on when the ferry departs, choose how many nights from that.

I too was ambivalent about Santorini. I went for what sounds like the same reasons as you: its a bucket list place. We spent two days there and that was enough. It was beautiful in a magazine way but I dont look back at photos of our time there and get a pang like I do of the other places we went. I think Im glad to have seen it because it gets talked about all the time and so now I know, and if you dont go you might wonder if you should have. The fact that there wont be cruise ships is a huge plus.

Now for Monemvasia and the Mani peninsula. Your itinerary will have a lot of driving. You can certainly fit it all in but it will be a whirlwind. From what you describe, Im guessing you will travel from Santorini to Athens, rent a car and drive to Monemvasia in one day. Arrive late (good, better for parking on the entry road) spend the next day there, sleep there, etc. Monemvasia is very small. We arrived at 5p, walked everywhere that night, and left the next day around noon. I dont know what we would have done with a full day, but then again, we were only there to sitesee the 'rock' and not things surrounding it (this was part of an 8 day road trip around the Peloponnese so we did see other things).

I like your itinerary! Your taste is much like mine (we did go to Dimitsana, Stemnitsa, Olympia...) - off the beaten path. I will say that the places we loved most were off the beaten path, which is maybe why Santorini was Meh. So the only thing I might change is how many nights I stayed in Chania, but thats a very small thing.

Thank you for the feedback. Yeah, that's my issue with Santorini, will I wonder/regret not going there? I don't know. You always have to make choices when traveling. I realize that I am mistaken though and the cruise ships will be operating this summer, or at least they are selling tickets. I swore I read on a Greece government site that they weren't operating but googling greek cruises the ads for the various big boys pop up.

Yes, it would be long day of driving to Monemvasia as you described - fly to Athens get car then drive down. I'm a bit worried about the ferry strikes. There is another one planned for the 16th and I suppose if the government doesn't negotiate they'll keep planning weekly ones. But as a friend said, when are they not striking in Greece, life goes on.

You could fly from Santorini, just to make sure you dont get caught in a strike

We drove from Monemvasia to Piraeus to catch a night ferry. The drive was completely doable.

We rented a car from Athens Car Rental, and they will meet you wherever you are, outside the place (port or airline, or anywhere for that matter) and the exchange of paperwork and car took 10-15 minutes. We picked up the car at the Athens airport, then dropped off at the Piraeus port. So you can arrange to meet them at the port or airport and it should be a quick turn around

edited to add: the ferry is a fun experience, but you will have it from Heraklion to Santorini, and the duration of the ferry from Santorini to Piraeus is longer than is interesting .... fwiw. IF the flight is faster and/or more dependable, you might want to consider it because of how much time you are spending driving (expedite the time between locations)

Jessica, you mention you were on a 28 days trip to Greece. I am planning to go there in September for 29 days. Could you share your literary, how long did you stay in each place, you advise if any?

Santorini is a beautiful island with the towns perched on the edge of the caldera. The Red Beach and the black beach at Perissa are fun and in great settings and the Akrotiri archeological site is also worth visiting. Back in the spring of 2016 we spent 3 nights in Oia and didn't ever feel the island or the town was overrun.

I felt no compulsion to go to Santorini when I visited two years ago, but this year I would probably take the risk that I could see it without as large of a crowd, and it does break up the ferry trip from Crete nicely.
I would have pause about all of the driving on the mainland, but then I just really do not enjoy being in a car unless it is taking me somewhere fabulous for a long time (not a day or two). I just don't feel like a few nights makes up for all of the driving. I would look carefully at the drive times.
Dimitsana is not a bad drive from Athens at all, so you could still see some monasteries, and there are some other convenient and impressive places you could fit in as well. Or, just go to Delphi and Meteora, and save all of the Peloponnese for a return trip (you can stay ten days like I did and not see it all).

I agree you could save the Peloponnese for another trip as you could spend a long time there

Eugene D - My itinerary was--
(rented car at ATH airport) - stopped at Corinth canal to walk the bridge
To Nafplio (3 nights, 2+ days) - Epidauros, Mycenae, Palamidi Fortress, beach...
To Nea Figalia (2 nights; small completely un-touristed village, chosen as a sleeping place for that reason. Midway between several things we wanted to visit) - En route drove to Dimitsana, hiked the Lousios Gorge from there past the monasteries to Stemnitsa, ate dinner in Stemnitsa, then drove to New Figalia (night 1). V. long day
Olympia in A.M., then to Temple of Apollo at Epikourios P.M. (night 2). Wanted to stop at Neda waterfalls but too tired
To Kardamyli, early (1 night, 2 days). First day sat on the beach at Stoupa ALL day ;) Second day hiked, then departed around 3p
To Monemvasia (1 night) - stopped in Githio en route for gelato. Arrived at 5. Spent 5 hours exploring the rock. Departed the following day at noon
To Piraeus for 9p ferry (1 night) departure (where we returned car) - stopped at Mystras en route
To Chania (3 nights)
To Loutro (3 nights) - this was special. Hiked the Imbros gorge instead of Samaria (we were traveling with three kids and they were still holding that Stemnitsa hike against us ;) )
To Kerames (3 nights - another small less-touristed village near things we wanted to see/do)
To Heraklion (1 night) - Knossos and Archeological museum
Ferry to Santorini - (3 nights/2.5 days) - hiked Fira to Oia, took a dinner cruise on a catamaran (!) for 5 hours around-ish the island, explored the usual places
Ferry to Naxos (4 nights? 5?)
Ferry to Athens - 2 nights/2 days....

I am reluctant to give advise because I seem to travel differently than the average RS Forum person. We are less interested in creature comforts and more interested in adventure, for now anyway. The catamaran tour was fun, but could have been a lot shorter duration for my taste. That was sort of a joke touristy thing that my Dh wanted to do and it was definitely different than our usual, so fun for that reason. I know people take tours and classes - we haven't done very much of that, so I cant advise.

I guess I would say there is a ton of information on this forum - go to previous posts, even years past. I got a lot of information from Janet and Stan in planning. But also be aware that everyone brings their personal sensibility to their advice, so what one person says might be too fast a pace, for example, or a must see/do, may not be true for you. Pay attention to the kind of traveler you are and your tastes, and then take advantage of the enormous amount the forum Greece travelers know about specifics

Thank you for the replies and suggestions. I've narrowed down as follows:

Day 1 - arrive late, overnight in Athens
Days 2-6 - Chania (5 nights in Chania)
Days 7-8 - Milia - rustic mountain area (2 nights) - 2ish hour drive to get there (2 nights here)
Day 9 - longer drive to Heraklion, hit Palace (and museum if we have time/energy) (1 night in Heraklon)
Day 10 - fly back to Athens then drive to Monemvasia hitting Mycannae and Corinth Canal (1 night in Monemvasia)
Day 11-12 - Mani penisula (2 nights in Kitta)
Day 13-14 - drive to Olympia then on to Dimitstana (2 nights in Dimitsana)
Days 15-17 - return to Athens (3 nights in Athens)

I'm still a bit nervous about the drives but they are separated and I really want to see these areas. I can spend all day in a museum but frankly I remember so much more when we've done shorter guided visits; I think left alone I get too bogged down in all the details. Lol.

Appreciate any feedback if you see any issues.