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Tuscany & Umbria Questions

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Just posting to the Forum for the first time. Planning a Spring Adventure in Tuscany and Umbria May 01 to May 22, 2010 and would like some expert advice as to what I need to think about including and/or fine-tuning. I am primarily interested in Religious Art and Romanesque Architecture, and am of a more a 'country mouse' than a 'city mouse' so I prefer smaller, more intimate locales to the big city experience. That being said, I do want to spend 7 nights in Florence to explore the Art and Architecture! I am excited about embracing the 'slow travel' concept, however my traveling companion is someone who likes to move on after a couple of nights. We both prefer the 'countryside' and would like to do some 'walking' . . . perhaps from one Tuscan town to another if possible. We will be relying on public transport which will restrict our travel substantially, but we'd like advice from anyone who has used the bus and/or train to travel through Tuscany and Umbria. My itinerary is evolving slowly, but I'm open to suggestions for 'tweaking' and 'fine tuning' the options, and adding towns that are a 'must see 'for frescos, art, and architecture!

May 1-2 Spoleto [2N]
May 3-4 Cortona [2N]
May 5-7 Montepulciano [3N]
May 8-14 Florence [7N]
May 15-17 Siena [3N]
May 18-19 Montalcino [2N]
May 20-22 Rome [3N]

Personally, I am not really comfortable with the number of two night stays as I prefer to stay longer in one place. I was initially contemplating a 7 night stay in Montepulciano and journeying out from there for day trips, but realize that may or may not be feasible with public transport. Any comments? I have also considered the following as possible places to stay: Orvieto, Spello, Arezzo, Pienza, San Gigignmano, Todi and San Quirico d'Orcia. I would appreciate any advice regarding whether it would be better to have two primary 7 night locales, and do day trips out or whether there are more preferred locales to stay regarding transportation. However, I do not want to limit myself to 'transportation links' only. Before anyone comments on the limited time in Rome: it is not my priority, and I am only including it because that was the flight option available.

Thanks!

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