Siena - staying in or outside walls
#2
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If your purpose is to be as close as possible to the center of town, stay at one of the places inside the walls. There are also several places to stay just outside the walls. If you are driving a car, staying just outside is usually easier unless your hotel can arrange inside parking.
#5
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The choice is an easy one. I've stayed twice within Siena's walls and will again in Spring of 2003. Outside the walls Siena is "just" another scenic Italian town. Within...it's truly magical! Parking the car in one of the convenient parking garages is no challenge.