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Debating Tuscan, Umbrian Hotels

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This posting is a bit premature as our May 2014 trip is in the early planning stages, but I have been trying to piece together a plan and am having a hard time choosing between various accommodations.

A little background... My husband and I are in our late 30s/early 40s and have limited time available for vacation. Years ago, we visited Florence and Sienna, but have not spent time elsewhere in Tuscany and have never been to Umbria. When we travel we enjoy experiencing/exploring art, history, great food and local culture (and just getting some R&R).

Generally, we look for small accommodations that have a sense of local character, great food, an informal feeling, and warm and helpful owners (preferably Italian owners on this trip). While we do sometimes stay at places that are a bit upscale, we try to avoid ones that have a sterile luxurious feel and prefer ones with character.

Sadly, we can only spare about 6 nights in Tuscany/Umbria. I'm considering basing ourselves part of the time in Val D'Orcia and part of the time in Umbria (but I'm not wedded to that idea). I know it would probably be best to just stay put in one hotel for those 6 nights, but I do like to move around a little and experience different areas and the hospitality of different hosts. At this point, we're considering...
Il Locando di San Francesco (in Montepulciano),
Il Fontanaro (in Paciano),
La Palazzetta del Vescovo (near Todi), or
Casa Fabbrini (in San Casciano dei Bagni).

All of them have strong appeal -- but each also has some drawbacks. Would love to hear (read) thoughts on any of them in particular or on any of the locations as a base. I apologize for writing such a long-winded post!

Thank you in advance for sharing your opinions and insights!

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