Wine and Dine in Montepulciano, Pienza and Montalcino

Posted by aislinnwalters on 04/03/25 05:49 AM

I will be spending three days/two nights in the Heart of Tuscany at the end of May. My husband and I will be renting a car and driving down from Florence. We are lodging in Montepulciano but we will also be driving to Pienza and Montalcino. We want to enjoy the beauty of the countryside and also partake in some wine tastings! I love wine, but am by no means an expert, and I am absolutely overwhelmed by the amount of wineries to choose from in the area, especially because I know some require reservations for tastings.

What are some of your favorite wineries in the region? I know the famous Brunello and Vino Nobile di Montepulciano, but what are some others? Also, if there are any recommendations for places to eat, I would like to consider those as well.

Posted by ChristineH

Gettysburg PA

04/03/25 04:09 PM

7713 posts

Plan to do your wine tasting while IN Montepulciano unless you have a designated driver or go with a tour
The alcohol limits in Italy are much lower than in US

Almost all wineries will require reservations
There are several shops right in town that offer tasting

Posted by Larry

Granite Bay, CA

04/03/25 04:48 PM

102 posts

If you love Brunello, then the Enoteca la Fortezza in Montalcino should not be missed. It has a huge selection of Brunellos to taste and buy. For individual wineries, I like Fattoria dei Barbi and Casanova dei Neri, but there are a lot to choose from.
In Pienza, we enjoyed Chiostro di Pienza's outdoor patio for dining, and nearby, in Monticchiello, is Osteria La Porta, with excellent food.

Posted by Larry

Granite Bay, CA

04/03/25 04:53 PM

102 posts

I meant to add, that in Montepulciano, Avignonesi winery offers tours, tastings, and a gourmet lunch paired with 7 of their wines, all overlooking the Val D'Orcia.
Not cheap but definitely worthwhile.

Posted by bethb

04/03/25 08:22 PM

153 posts

We liked Patrizia Cencioni winery/vineyard outside Montalcino very much - run by a woman and her daughters.
https://patriziacencioni.com
Casanova de Neri seemed more corporate, it's a lot bigger estate. I didn't like the tasting experience as much, though the wine was excellent!

We hired Fabrizio from Ciao Faby Tours to pick us up form our accommodations near Montalcino for a day of winery visits, tastings, and lunch at a sheep farm outside Pienza. Fabrizio (Fabry) was fantastic - warm, funny, and very knowledgeable, and definitely had a lot of local connections. I believe he also does cooking classes at his home in Montepulciano!
https://www.ciaofabrytours.com/best-private-tours-in-tuscany/exclusive-private-wine-tour-in-tuscany/

Our favorite meals in Montalcino were:
Re di Macchia
Il Grifo
Taverna Grapolo Blu

Posted by sanomh

04/04/25 01:06 AM

301 posts

In Montalcino we ate at Il Moro for lunch and really enjoyed it. Not fancy, but good food and service. It's family run, and seemed like there were many locals eating there. We didn't have reservations, not sure they even take them, but had no trouble getting a table for 4 at about 12:30pm on a Tuesday in mid March.