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Summer in Tuscany - Need advice/recommendations

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My entire Italian vacation last summer consisted of advice I received on this board during the planning stages. Once again, I'm looking for any information or direction in planning another vacation for July of 2010.

The first trip last summer was throughout Northern Italy; Summer 2010 I'd like to spend exploring Tuscany (specifically the hill towns). I will have 14 days (not including international travel days) to work with. So far, I've got it narrowed down to Lucca/Pisa, Florence, Siena, Cortona, Montepulciano and Orvieto. I know that 14 days is not enough time to explore all of these cities. Do you have a suggestion on which one/s I should Axe? Am I missing an important hill town?

I don't particularily care to stay in Florence for too long, just enough time to see the Duomo and the Museum. I particularily like cafes', shopping, photography and walking the streets. I'd like to rent a bike and/or Vespa to get around town and maybe a car if needed to go from one place to another. I don't drive a stick...so that may be an issue. I'll also be traveling alone.

My flights are not purchased. Ideally, I'd like to fly in or out of Venice. Even though it doesn't make much travel sense, it was my favorite city and I'd like to spend at least 1 full day there again. If at all possible, I'd like to stay clear of Milan airport (pain in the ARSE, plus the train station scared the beejesus out of me!). That leaves florence or rome as an alternative airport.

I've started looking at Convents/Monastaries as a budget alternative to hotels. Are there any in these towns mentioned above that you could recommend?

This is my starting point (beyond books)...so any advice would be very helpful!

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