There are Italian hill towns, and then there is Cortona. Rising dramatically from the Valdichiana plain, it has been inhabited since before the Romans — and it looks it. The medieval clock tower, the crooked stairways, the worn stone piazzas, the views that seem to stretch halfway to Rome — there is nowhere quite like it in Tuscany, or perhaps anywhere.

Frances Mayes put Cortona on the world's map when she bought a crumbling villa on its slopes and wrote Under the Tuscan Sun. Millions of readers fell in love with the place through her words. Today you get to walk it. The light is extraordinary. The views are extraordinary. The whole afternoon will be extraordinary.

This is the optional Carmela personally recommends above all others on this itinerary — and guests who've been before always wish they'd signed up.