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Tuscany & Umbria

Returning to Italy for our 5th trip but have not been back to Tuscany for 6 years and first time in Umbria. We will have a car and staying in Spoleto 3 nites while in Umbria and Montepulicano 3 nites while in Tuscany. Last time in Tuscany stayed 4 nites in Siena as a base. What suggestions do you have for Tuscany (have been to all the touristy hill towns) small wineries, small towns worth seeing. Also what not to miss in Umbria?