Le Marche suggestions?

Urbino is a Do Not Miss. The Frassasi (sp?) Caves are pretty terrific. If you go to their web site, you can probably find out when the tours in English are scheduled, and maybe even reserve tickets. We also liked Ascoli Picieno.

I love Senigallia. It’s a good base for exploring the area — the Caverns of Frasassi and the medieval hill town of Corinaldo are nearby. Great restaurants — two with Michelin stars. We were there in early October & things were getting quiet but still lovely.

Thanks Rosalyn and Charlene. Do you remember the restaurant names, Charlene?

Ascoli Piceno has a beautiful pedestrian-only piazza, Piazza del Popolo, great for morning coffee or an evening drink. A must-eat are the Olive Ascolane (Ascoli Style Stuffed Olives). We had them, as well as a delicious lunch, at Migliori Olive Ascolane on Piazza Arringo. Buon viaggio.

Camerino is pretty interesting .

We spent a week in Le Marche last May and split our time between Urbina and Sirollo, to get both the mountain and sea. Both were fabulous. Urbino is very hilly. Parking is outside the walls; there are free lots, but it was hard to find a spot. We found it best to park in a huge garage on the edge of the town (has a small mall on one of the stories) and take the elevator to the top of the town. In Urbino we had a great dinner at Antica Osteria Stella. Sirollo is a beautiful village on the coast. The town piazza overlooks the sea and the views are amazing. We ate at LaRosa, Tavernal and Osteria Sara. All were excellent. We were served little "extras" on the house, such as soup, an appetizer or a liquor at each place, which is a nice touch. One of the things we liked best about this area was the lack of masses of tourist. Enjoy!

What month? What kind of stuff do you like to do?
I'd choose one north and one south spot (depending on your Umbria itinerary), or one coastal and one inland.
We loved Senigallia, where our favorite meal was at Pagaia. I'm going to assume you love seafood! We visited Sirolo as a day trip to hike and visits the scenic beach, and I also considered staying there, but the attraction of a seaside old town in Senigallia was too great to resist.
Ascoli Piceno was also wonderful. It puts you close to the mountains and lots of great hikes.
The caves were a highlight.
There are hundreds of pretty little hill towns, but accommodations somewhat limited -- lots of agriturismi, but we prefer staying in a town. Driving was easy, but slow except for the autostrada.

Thank you all for the great ideas. We will be there early October. I doubt it will be warm, but we still like to visit the coast and love seafood. We hope to stay near Pesaro a couple of nights, a couple of nights in the hill towns and then 1+ near AC.

Thank you all for the great ideas. We will be there early October. I
doubt it will be warm, but we still like to visit the coast and love
seafood. We hope to stay near Pesaro a couple of nights, a couple of
nights in the hill towns and then 1+ near AC.

There is a coastal park starting just north of Pesaro called San Bartolo that is full of pretty little villages. Just gorgeous! I liked it just as much as the Monte Conero area that includes Sirolo/Numana/Portonovo--both are the gems of the coast in terms of natural beauty. Another reason we chose Senigallia was so we could visit those two parks places just to the north and south (40 minutes drive or less each way) and enjoy dining at night on foot. It made a convenient base. I hope you have good weather!

The two-Michelin-starred restaurants in Senigalla are Uliassi and Madonnina del Pescatore. Both very pricey, and reservations recommended.

There are many other great restaurants in Senigallia. We really enjoyed La Tartana, right on the beach. We noticed it our first night there, while wandering along the sea. They had tables in the sand, so it became our spot for an apertivo ... a glass of wine or aperol spritz, perhaps, with a nice assortment of complimentary finger foods. We lingered so long one evening that it was dinner time, so we moved inside and had lovely plates of fresh pasta with seafood.

Charlene, you've sold me! Especially in Italy and Spain, I've loved the bars where you're right on the beach but can enter without getting sand in your shoes!

My evening at La Tartana started out very promising--nice wine, nice appetizer, but when my husband was served raw shrimp, it took a negative turn. We have eaten raw seafood all over Italy, but raw shrimp should result in a headsup. We tried to be very accommodating, but the manager's attitude soured us on the place. That is all just to say order carefully!