For wine enthusiasts Montalcino and Montepulciano are heaven. The first for its famous Brunello wine (Brunello di Montalcino) and the second for the Vino Nobile de Montepulciano. Both are medieval towns and on Hilltops so the views are incredible. This also means that you will have to walk steep streets. We were based in Montalcino for some days and drove to Montepulciano for a day visit. Approx. 1 hour drive and parked below Fortezza di Montepulciano (P n.8).
Montalcino was until the 80’s a poor town that blossomed when the Brunello wine became world known. Going from a small selection of wineyards to over 100 today. The town itself is very small, most visitors come mainly because of the Brunello wine which is sold everywhere in the town center. There are many wine shops which you get charged for tasting. You can easily spend hours going from shop to shop tasting what seems to be endless selection of Brunello wines.
There are 3 restaurants we liked, Osteria di Porta al Cassero for lunch. Il Re di Macchia and Locanda Demetra for dinner. Apart from the Brunello, Montalcino town is cosy, but not particularly exciting. It’s the surrounding areas with the wineyards, castles, beautiful landscapes that make Montalcino such an amazing place.
Montepulciano is a bigger and dynamic town with more people, wine shops, restaurants, cafes, galleries and stores. We spent a day here and strolled in the beautiful narrow streets. Head to Piazza di San Fransesco for a scenic view. Unlike Montalcino, wine tasting is not charged. Understandable seeing that Vino Nobile is generally less expensive than Brunello.
We recommend having lunch at Osteria Acquacheta. Great place and food, but prepare to share your personal space with complete strangers. The concept here is to seat guests together, litterally filling up each table and guests are not given the option to sit at empty tables. Was awkward the first 10minutes, but you get use to it. We liked it here. After that have wine tour and tasting at Contucci winery near Piazza Grande.
We liked both towns, allthough we did spend most time in Montalcino. We would visit again.