So after all that, I decided to change my itinerary slightly! As much as I want to see/stay in Senigallica, I decided we wanted to be closer to Ascoli Picente for a bit longer, and I realized that my husband probably wouldn't really enjoy being on a crowded beach as much as I would (his bald head and British skin). I still wanted to be near the sea though, and since Sandra recommended the area of Porto San Giorgio, I looked on a map at that region and found a tiny village on a hill overlooking the sea called Torre di Palme that looked sooooo pretty and isn't far from Porto San Giorgio. So I can get my fix of a crowded beach while my husband has a choice to be somewhere a bit less hectic.
SO...Unless we change our minds again, our itinerary is as follows, although still needing to make a couple of final decisions on how many nights to stay in one place vs. anogher...
Sun July 1-Thurs July 5th - Rome, an apartment/loft in Trastevere (via airbnb)
Thurs July 5th-Sat July 7th OR Sun July 8th - Ascoli Piceno, via booking.com, an apartment in the historic city center
Sat July 7th OR Sun July 8th-Mon July 9th - Torre di Palme, a B&B right in the village overlooking the sea (via booking.com)
Monday July 9th-Thursday July 12th - an Agriturisimo in Mondavio, where we can visit Senigallia and Urbino fairly easily (via booking.com). Flying out of Bologna on July 12th, at either 11am(ish) or 6pm(ish)
All lodging is in the 100 euro range per night.
I have time to adjust the dates if needed. I am having trouble deciding whether I want to stay 2 or 3 nights in the center of Ascoli Piceno, or 1 or 2 nights in Torre di Palme. The two towns are pretty close to each other, we're just switching b/c we like variety and I wanted to be closer to the sea for at least a little while even though it isn't my husband's main priority. Neither of those two places are air-conditioned, so that could be a factor in my decision. In July, will it be a little bit cooler on a hill above the sea? That could be a reason for 2 nights! Does it cool down at night either way? Then maybe it doesn't matter.
Any thoughts/feedback on places to eat or visit in any of those towns or the vicinity would be welcome, although we're definitely developing a plan of action of our own using the Blue Guide of Le Marche and San Marino!
It's quite a bit of moving around, but like the last poster said, there are pros and cons to that. We generally like having different lodging experiences and b/c it's our first time in Italy, I like the idea of moving around a bit more.