Tuscan Hill Towns

Montalcino, Pienza, Montepulciano, and the scenery in between.

During our three-day stay in Siena, we took a day trip these Tuscan Hill Towns. Montalcino is very mellow, which complements its star the Brunello de Montalcino, while Pienza is a planned Renaissance hill town, and Montepulciano is the most impressive with its medieval cityscape and cavernous wine cellars snaking under the city.


Sitting atop a hill surrounded by a sea of vineyards. This is the home of the Brunello, the pricey 100% Sangiovese red wine. This is primarily why we are here as the enoteca enticed us to try then buy wine. The best offering was near free shipment on a case of Brunello. But what made this experience truly wonderful was how empty the town was and how great the proprietor of the Enoteca di Piazza was in letting us try a variety of Brunello and calling out his favorites and his recommendations for something we would not be able to get in the U.S.

There are few sites here besides wandering the town. The best view come at the Fortezza, which is the ruins of a 14th century fort built under Sienese rule. Alongside the city hall are a series of stone plaques, which show off the annual rating of the Brunello harvest.


Pienza was admittedly not on our “must see” itinerary until we read about it in Rick Steves’ Italy guide book. The history is fascinating — in the 1400s Pope Pius II remodeled his birthplace into a “city fit for a pope” in the Renaissance style. Pienza’s architectural focal point is the main square with the Duomo and the Pope’s family residence. This is a quick stop and allows for a nice little walk along a street grid plan. Here we had a little snack of charcuterie as we meandered the fairly empty lanes.

We have it on good authority that the town becomes lively in the height of summer but in April, we were the only tourists among locals. This is a great little stop off to stretch our legs between Montalcino and Montepulciano.


Montepulciano might be the best part of this day trip. Between the meandering medieval hilltop lanes to the Palazzo Comunale, or town hall, to the deep cavern wine cellars interlacing tunnels beneath the town. The central square is a beautiful microcosm of Italy — the Palazzo looks very Florentine, the Renaissance Palazzo Targum and Palazzo Contucci, and the dimly designed duomo.

A highlight of our Montepulciano tour was walking into the most impressive wine cellar in the town – De’ Ricci Cantine del Redi. Just a few steps off the main square, there is an unassuming door, and then a lot of stairs down. To be honest, we felt like we shouldn’t have been there. We walked down, and walked down some more, and then it got cold, chilly, and damp. We turned a corner and we came to the largest wine cellar we’ve ever seen with barrels 20 feet tall. Finally, we wound up in the shop where we tasted the famous Vino Nobile de Montepulciano. Having a perfect snack and this wine made this trip to the Tuscany Hill Towns so memorable.

Note: This post recounts a trip to Italy from April 2016 and some information may have changed.

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