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Le Marche - Two Locations for Trip : Ascoli Piceno and ???

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I am thinking way ahead to a trip planned to re-visit the southern area of Le Marche and Ascoli Piceno and area. But also this time to travel to the Northern ends and I am trying to decide on a place to lodge for several nights.

We are not beach lovers and also will not be there at a time when beach is even an option so I am thinking of places more inland (i.e. Urbino maybe rather than say Ancoa for instance). But I am reading that Urbino is very steep plus a problem for parking. We will have a car and we do enjoy both staying in small towns/villages but also in small B&B's / agriturismos slightly away from town, especially if we want to, as in this case, to not just "park ourselves" in one city center to explore only that city, but want a base where we can day-trip in the area.

I would love to hear suggestions and advice on where to stay from people who have been or have knowledge.

Thanks in advance!!

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