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Tuscany itinerary critique please!

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Itinerary critique please?
May 21, 2014, 4:38 PM
Hello,

My husband and I will be driving to Tuscany from Venice and then staying in the wonderfully reviewed Hotel Vecchio Asilo (near San Gimignano but not in it). If I had been able to research a bit more ahead of time before booking, I would have split Tuscany into 2 B&Bs, one north and one south. But as it is we are pretty central. We already have been to Florence and so can skip it this time in favor of small hilltowns. We will have 4 and a half to 5 days in Tuscany, 5 nights. We like hiking, walking, exploring, scenic driving. So I'm not quite set yet on how much we can see but thinking one day for Siena, one day for Lucca and Volterra, one day for Southern Tuscany-Montalcino, Montepulciano,San Quirico d’Orcia, Pienza,etc., one day for the Maremma. I really want to see Pitigliano, Sorano, and Sovana and walk through the Vie Cave. l am thinking a hike through those Maremma hilltop towns and the Vie Cave will be really memorable for us. Would like to get to Monteriggioni and Carrara as well but not sure if it fdits in anywhere or if it's doable. Don't really know if we can/should do all this as it seems like a lot on paper but some of those little towns seem very close together and tiny. I'm thinking long days and getting back to our B&B late in the evening and sitting outside in the garden drinking wine and putting our feet up! Any feedback is welcome and thanks so much

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