Trip Itinerary

The general thinking is that Hydra is a convenient island for folks who don't have time to go farther afield. Since you're going to several other islands, I wouldn't bother with Hydra. Having a condensed 4 or 5 nights in Athens would allow you to do a pretty deep dive into the local museums. Or you might try to squeeze in Nafplio on the mainland. Or you might add a bit of time in Crete. That has always seemed to me like an island that needs at least a week. It's quite different from your other islands and quite large, with a mountain range down the middle.

Is the 1 night in Athens because you’re flying from Rhodes to Athens, and you don’t plan to get to Hydra the same day? I know it’s only a 1-hour flight between Rhodes and Athens, and there are several flights a day, but I’d try to get to Hydra right away, and minimize the 1-night stands. Rick Steves does say that of all the Greek islands, Hydra’s his most favorite.

Then again, on Crete, would you consider a night (or possibly more) somewhere other than just Hania/Chania? Maybe Iraklio/Heraklion? The archaeological museum there, and the ancient Knossos site just south of the city, are among the top sights in all of Crete. When done, the ferry from Iraklio to Santorini is more direct, and faster than flying from either Hania or Iraklio, if that was your plan.

I agree with acraven about Hydra. Add that night somewhere else. Crete or Rhodes makes the most sense.

Why do you have one night in Athens and then after Hydra 2 or 3 nights in Athens? That is wasting a lot of time because it takes an hour by taxi to get into Athens from the airport. If you drop Hydra, then you can condense your stay in Athens. So you could add the Hydra night to Athens for a stay of 5 nights in Athens. Or as I already suggested, add the Hydra night to Crete or Rhodes.

I like your allocation of 3 nights for Santorini, which is what we did. We spent a day visiting Fira and Oia. And on our second full day, we rented a car and visited the Akrotiri archaeological site, the Akrotiri lighthouse, red sand beach and black sand beach. It was one of our favorite days. The caldera is stunning, obviously, but seeing the rest of the island is very worthwhile and I think makes for a more rewarding trip.

Five nights in Naxos or Paros is good. We visited Naxos and loved it. Haven't been to Paros so I can't compare. While we were on Naxos, we rented a car for a day to visit the mountain villages and fishing villages, and had an awesome lunch of fresh fish and shellfish at a fish taverna about a foot from the Aegean Sea. This was another one of our favorite days.

RIck steves for some reason doesn't really favor the Greek Islands.... his tours only do mainland (Maybe because it's easier and more economical to zip people around in a bus rather than take them aboard ferries or planes) ... he always suggests Hydra for Rick-Heads taking his tours, because it's an easy day-trip add-on. But when you've been to the isles you list, Hydra is unnecessary and may even be a let-down. (as another adviser said, on a recent thread, It's OK to disagree with Rick).

The one Outlier in your list is Rhodes... because it's not on the Route. You're OK for 1st 3 stops (Fly to Chania, then get to Heraklion for AM ferry too Santorini; then many choices of ferries to PAros/Naxos) .. but then what? No real ferry connection (there used to be a wonderful 3x week Blue Star that stopped at Santorini about midnight & you woke up in Rhodes -- but alas no more). You get a 2-part flight - back to Athens out to Rhodes... less than 3 hours I hear.

According to your planning you seem to be arriving in Chania directly from Dallas?
You are likely to have a layover at Athens airport before.
Have you checked the possibility of being in Crete from the first day?

As janet told you, adding Rhodes to your trip isn't going to be easy.
Rhodes is in the Dodecanese islands which are not in the same group of islands as the others you want to visit.

Provided your dates match the ferry schedule, it will take at least 10 hours by ferry to get from Santorini (or Crete) to Rhodes. and there are only 2 or 3 ferries per week for this route.

As indicated above, it is useless to go to Hydra if you are already spending your time in other islands. Hydra is just a convenient destination to visit a Greek island from Athens when you don't have time to go to other islands