Need Help - Leaving this Friday
Hi from Montepulciano!
Consider that now is stillhigh season in Tuscany, and finding an accomodation in town could be not so easy.. You could try to contact Strada Del Vino Nobile, www.stradavinonobile.it, the local tourism board, to check if they find you any availability ..
About restaurants, in my opinion there are only 2 restaurants "not to miss": La Grotta, just next to San Biagio church, and "Osteria Acqua Cheta" , in Via del Teatro. For an apéritif with a view, "E lucevan le stelle" in Piazza San Francesco ( near Piazza Grande).
We were in Montalcino and Montepulciano a few weeks ago. We chose to stay in Montalcino because we love brunello wine. We had an outstanding lunch at Il Leccio in Sant'angelo in Colle (you must eat the homemade pinci pasta), after going to a wonderful tour and tasting at Ciacci Piccolomini d'Aragona which makes fabulous brunellos. In Montepulciano we loved the florentine steak at Osteria dell'Acquacheta (and the owner is quite a character) and we enjoyed our tour and tasting at Avignonesi winery.