Help plan Oct trip starting in Crete, Santorini, Meteora, Delphi, Athens

I would spend your time like this.
7 nights Chania or wherever else you want to go.
1 night Heraklion . Go to Knossos and the archeological museum. You can rent a car to pick up in Chania and drop off in Heraklion. That is what we did.
3 nights Santorini (fly to Athens after and rent car at airport)
1 night Delphi
2 nights Meteora, return car at airport
3 nights Athens

Exactly what BethFL says.

I agree with Bethfl's plan.

The Santorini-to-Delphi trip via Athens will be a busy day, take an early morning flight from Santorini, either Sky Express or Olympic (not Ryanair).
The flight takes about an hour, and you’ll need time to disembark and handle the car rental paperwork. It takes at least 2.5 h to drive from the airport to Delphi (more likely 3h). And you'll probably want to stop for a lunch break.

The Delphi site closes at 6:00 PM in October, with last admission 30 minutes before closing.

So, do the math.

Thank you for all the tips!

Is there a reason why flying from Chania to Santorini is not suggested?

I know that having to stop in Athens is not great, but the flight time is only 2hr 30min on Aegean air and the ticket cost is actually a little cheaper than the ferry tix, no need change hotels, and drive across the island to stay at the port in Heraklion for the night (which adds 1 more night to my stay on Crete). Seems like we'd lose a day that way with the time and expense of driving across the island. Just trying to figure this out.

If the flight is not that bad of an idea, that gives me one more day on the mainland to start the trip from the Athens airport on Sat Oct 17th, there is a flight that would arrive at 10:10am (incase there are any delays, there are still flights after this one) get the car and start the drive to Delphi, maybe staying that Sat night in Arachova and head to Delphi first thing in the morning, then later head on to Meteora and spend 2 nights (Sun & Mon), then would have Tues to stay somewhere interesting on the drive back from Meteora (Galaxidi?? suggestions??) Wed drive to Athens for last 3 nights. This gives a somewhat leisurely pace?

Sounds good in my head, but please tell me if reality is diferent, :) :) :)

Thank you!

Yes, you can certainly fly to Santorini via Athens if you want to avoid an overnight stay in Heraklion. Note that Aegean and Sky Express are currently offering discounts of up to 50%, I’m not sure if this applies to the specific flights you’re looking at, but be aware that the offer won't last long. I posted about this 3 days ago:

https://community.ricksteves.com/travel-forum/greece/discounts-up-to-50-on-aegean-olympic-and-sky-express-flights

The rest of your mainland itinerary starting on the 17th works well, too. Since you have to leave Santorini that morning anyway, you could take the 8:25 AM flight (arriving at 9:15 AM). though perhaps you aren't keen on getting up that early.:-)

I don't have a specific suggestion for an overnight stop between Meteora and Athens. My next trip to the area, whether it happens in a month or a year, will definitely be to the Pelion region. It’s not well known among foreign visitors.

It’s roughly located between Meteora and Athens but along the coast forming a sort of peninsula, if you decide to check it out, let me know what you think, though a single night is probably too short a time.

https://www.discovergreece.com/travel-ideas/cover-story/explore-12-unmissable-villages-pelion

Part of my thinking is that Knossos and the archeological museum are very worthwhile stops in their own right and one of the premier sites on Crete. In other words, going there is not a waste of a night.

But, of course, if you have no interest then flying might make more sense.

Since there will be a lot of sites also to be seen on the mainland, I am not too worried about not seeing Knossos when it would require having to drive across island and change hotels, as it looks like we will be doing a lot of that after Crete.

Thank u for the tip on the flights. This route is slightly discounted. Since it would be a connecting flight, I would definitely want my luggage to be carry on, but I see that they have an 8kg limit on carry on bags. That is where the challenge might be with a flight. Risking checking in luggage

If you're worried about going over 8 kg, buy a Comfortflex ticket for an extra $30. If you have to pay for it last-minute at the airport, it’s going to cost you a lot more.

We’ve already had layovers in Athens with short connection times on Aegean. Last time, we only had a 50-minute scheduled layover (on a single ticket) with checked bags to catch a second flight to Thessaloniki. The first flight was delayed, and our connection time dropped to 25 minutes. We still made the second flight, and our checked bags made it too. When you get off the first flight, you’re in the same terminal area as the boarding gate for your second flight. At worst, you just have to go up or down a flight of stairs.

That being said, anything can happen at any time, but in any case, since it's a single-ticket journey, whether it’s a delayed flight or an issue with checked luggage, Aegean will handle it for you.

Awesome, thanks!