Thank you to everyone who has posted on my years-long planning thread: https://www.fodors.com/community/eur...h-help-1085396
I am starting a new thread now that the itinerary has shaped up (and five pages was a little onerous).
Here is the plan, and if you have any suggestions, please share. Special interests: food(!), birra artiginale, pottery, hiking/nature (formal/botanical gardens also), archaeology
I'll add any last-minute questions here as well. As always, nine days is not enough and the sheer number of appealing hill towns is dizzying.
Late May, arrival and departure Ancona airport, w/ rental car.

Ascoli Piceno, three nights. I'll be content if we don't even leave the city, but I am still researching hikes in northern Gran Sasso or southern Sibilline. If that does not materialize (weather could be iffy, but too soon to tell of course), I still have the immediate region to research--cross-referencing locales with multiple books is not easy! The day we leave, I was thinking we might check out San Benedetto del Tronto and/or Grottamare (but that would mean leaving luggage in trunk, an annoying concern on travel days). Or, maybe we'll take the long way and stop in Montottone to shop for pottery.

Senigallia, three nights (I had hoped to stay here last for proximity to airport, but accommodation availability determined the order)
We'll definitely visit Monte Conero for hiking and possibly San Bartolo coastal park to the north (checking out Fano and Pesaro--archaeological museum). The day we leave, I hope to stop in Mondavio and look for fava bean flour products, perhaps Fratte Rosa for pottery.

Sassoferrato, three nights. This is the peace and quiet portion of the trip, and I found a nice apartment in what seems like a convenient spot. We'll certainly be exploring Gola della Rossa for hiking, possibly tour the caves (I dunno, I've maybe done enough underground tours in my life, they can cause anxiety). I think we can flip a coin and set off in any direction and be pleased here.

Last night, we'll stay in an agriturismo within a 30 minute drive to the airport. I have a few contenders, but please share if you have a suggestion.

AIRPORT QUESTION
Our flight is at 10am, but the rental car office opens at 8:30, and I would rather do a face-to-face drop-off. Given that we will do online check-in if able, have carry-on luggage, and our flight is to Germany, do you think that it would be okay to arrive at 8:30, drop the car, and proceed to gate?

Topping my post for any last-minute tips before we head off next week. Fingers crossed the unsettled weather will settle down!
I would especially appreciate feedback on the airport question. I suppose we could pay for the extra insurance and then we would have no worries whether the car is checked by a human at drop-off or not. But it's double cost for peace of mind...

Buon viaggio, yorkshire! Sorry, I don't have any airport info for you. It's the kind of thing I'd stress about a bit too.

In Ascoli, if weather is okay you should be able to hike in the Sibillines or at least do some walks. Really depends on how far you are willing to drive. I loved the inland drives from Umbria to Ascoli and then we drove down to Naples through Abruzzo and skirting Lazio--all very beautiful--so some good places nearby, more than I could squeeze in. Try to get to Civitella del Tronto if you can. We tooled around on bikes; there is an abbey nearby too. that you can visit.

I *think* we enjoyed a couple of simple but excellent meals at Ristorante del Corso in Ascoli. I was using a Slow Food guide, I believe. Lunch was better than dinner, for what that's worth. There was a fish special del giorno at lunch that I ordered and my dining companions were jealous. So get the special if you go. Do partake of olive ascolane. I thought they would be too rich or fatty for me--I can be a bit of a light eater at times--but nope, totally addictive and never spoiled my appetite.

Please do enjoy your visit. I would love to go back!

We also had very simple pizze and insalate at La Nicchia. But perhaps we most enjoyed the aperitivi scene. In any case, this was two years ago and I hope to read about your new discoveries!

I have not flown through that airport but have driven by in the train on the way to senigallia it is tiny, and i think you’ll be ok with doing drop-off at 8:30 and then proceeding to security and gate, seeing you check-in online and have only carry-on. I’d say go ahead. On another note, we’ve done non-face to face drop offs many times and never had any problems. I always make a little video of the car before dropping it off, just in case, but never had to use it.
as for food in senigallia, with which i am obsessed and totally in love, have a look at this thread (replies update opinions over four visits in four months): https://www.chowhound.com/post/eatin...1049673?page=2

Thanks everyone, that is reassuring about the airport.
For personal reasons, I was unable to do the obsessive research I usually do, but after six trips to Italy, I figure I can wing it (let's hope).
Vinoroma, I have read about the Michelin starred places in Senigallia, but do you have any low key (rustic seafood is our thing) places to recommend?

Did you follow the link i posted and read through it?

Oh duh I had missed that--loved reading about da Maria, thanks!

Thanks again--we have now settled on Fano for our last night (I was waffling on where to stay close to airport) and have our hotel working on a Da Maria reservation (we are to try again the day before, as two weeks is too far in advance). It sounds like just our kind of place and a great way to cap off a trip.
Your birra artiginale mention was also helpful--my husband brews his own beer, so the explosion of craft beer in Italy has greatly improved his dining (not so much our dinner tabs).