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Tuscany accommodation conundrum

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File this under the most non-problem "problem" I've probably ever had. :)

I'm traveling to Italy with a friend in May and we plan to be in Tuscany for five nights (May 8-13). This is not our first trip to Italy, but is our first trip to Tuscany. Right now I've found the following options in our budget:

1) My first choice - an apartment just outside Montepulciano. The place looks fantastic, gets great reviews on VRBO, and the location seems great. I like that a town is so close but we're still in a farmhouse/agriturismo environment. The issue is that she does not have availability for May 8, so we would need to find somewhere else to stay. Normally I don't do many one-night stays, but I thought we might stay at a b&b near San Gim or somewhere else like that for one night and then come here. If that is a sensible plan, any recommendations on which town to pick would be great.

http://www.poderepoggioalsole.it/?p=849&lang=en

2) This agriturismo is near Montalcino. It also looks great, gets great reviews. We thought about taking a full-day cooking class in Cortona, so it would be further from that if we choose to do it, but otherwise I'm not sure whether it's more or less convenient to towns and attractions than #1.

http://www.agriturismocunina.com/

3) There's also this place near San Gimingnano. I had concentrated more in the Pienza/Montepulciano region, but this place looks beautiful too and has availability.

http://www.casanovadipescille.com/

I think there's probably no "wrong" choice, but any input on the best right choice would be much appreciated!

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