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La Marche region/Italy

Last May had a wonderful trip by car to and thru the hill towns of Tuscany and Umbria. Now this coming May we want to visit east of there. Fly into Rome and head towards the "bottom" of the area, Ascola. May stop briefly on the way at L'Aquila as this is where we purchased our wedding rings several years ago. We would like recommendations as to other towns we might like to see in La Marche. We like medieval environments. We know of Urbino and plan on visiting there. Will be on the ground in Italy 13 days. Would like to spend at least a week or so in La Marche then head to Ravenna, then to Bologna then to Milan and the airport. We are not particularly interested in seaside destinations unless they are special. Suggestions would be MOST welcome. Thanks in advance.

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Gubbio, San Leo, SanSelproco. Visited all last September on a self guided bike tour. Wonderful towns. San Leo totally undiscovered, TINY, with a wonderful fort above it on a hill, easy to walk up to see. SanSelproco offers an old walled city within the modern one. Gubbio, take the cable car to the top of the mountain for great views and a fun experience.