Thanks, JoLui -
I think I'll be giving that helicopter service a hard pass. While I do love me some occasional travel by whirlybird, only under the right conditions. And those conditions include fares that do not run into 4-digits for just a short hop...such helo flights are not impossible to find (have done them before, am doing another soon, actually), but helicopter flights tend to be either expensive, or exceedingly rare and generally obscure...but yeah, those in your link are eye-watering.
Speaking of eye-watering fares, it didn't take me long exploring the links you provided to stumble across what appeared to be standard, even routine, ferry hops, but with price tags north of €130. That's for just a seat, not a stateroom or for taking a vehicle, and not a super-long crossing. Heck, with ferries at that price, I might reconsider the helicopter - nah. But fer cryin' out loud, that's an expensive ferry ride.
I'm taking a slightly unconventional approach to booking transportation for this trip. I'm trying to skip Athens altogether on the inbound (because flying via Athens, I'm finding lots of night-time arrivals, or loooong, overnight connections - or both - most of which look like a pretty miserable way to end your flight to Europe (I'm coming from the far northwestern corner of the USA, which contributes to flight schedule challenges, it takes a full day plus an overnight to reach Athens from where I live, so I don't want to inject a second overnight into "just getting there").
So rather than flying to Athens and getting off the plane, switching to a local carrier, and pushing on through my second night of travel to eventually arrive at an island, I'm looking at connecting somewhere else on the continent and then flying directly to an island - in fact, all the way to "the end of Greece" in the far south/southeast, eg possibly Crete or Rhodes (I've been surprised to find more options to do that than I had first expected). Once we get there, and start the actual time in Greece, we would work our way back with some island hopping, possibly a combination of short direct flights (which as you correctly point out, are indeed limited, but some do seem to exist) and of course filling in the gaps with ferries when flight options are crazy or non-existent (which I know is most of the time).
I am loathe to fly from one island to another by first flying back to Athens, that seems crazy - but I am learning that crazy is not unheard of in this corner of Europe. After the island hopping, we would head back to Athens (not sure of flight or ferry, haven't decided on our island list yet), then spend the last bit of the trip on the mainland, including (but maybe not limited to) Athens. Flying out of Athens after that.
I'm still in the very early stages of figuring things out. And yes, the ferry links are definitely head-explosion material. We'll see how this goes, but I'm starting to get a general sense of the flight options; but I'm still just scratching the surface on the ferry options. When I saw those €130 ferry tickets it was definitely a coffee-spewing moment.
I'm probably going to step away from the Greece trip planning for a few weeks (we have a trip to Italy coming up in two weeks, and I need to wrap up some stuff for that and start packing). Will pick back up the Greece planning in October after we get home.
Thanks again for sharing insights and resources.