Vino Nobile, winding streets and sweeping views of Val d'Orcia and Val di Chiana.

Montepulciano, image by Edward Riddell

The narrow streets of Montepulciano


Montepulciano, image by Edward Riddell

The narrow streets of Montepulciano

Originally an Etruscan settlement, Montepulciano was founded around the 4th century B.C. due to its excellent position which allows you to see both Val di Chiana and Val d’Orcia. The town was long contended by Siena and Florence, ultimately flourishing under Florence throughout the Renaissance, during which Montepulciano became the Medici’s outpost in the South of Tuscany, partly in merit of the strategic routes that passed by it.

The link is even more evident when observing how similar, if not identical, Montepulciano’s municipal building and Florence’s - Palazzo Vecchio - are. This resemblance was strictly demanded by Cosimo I de Medici.

Montepulciano has always been an important place, it was a garrison (group of troup settlements), during the rule of Ancient Rome and a noteworthy religious centre during the Longobard reign.

Cantina Contucci, Montepulciano

The view from Montepulciano

Vino Nobile di Montepulciano

Cantina Contucci, Montepulciano

The view from Montepulciano

One of the oldest and most refined Tuscan wines, produced from a grape variety known as Prugnolo Gentile, a clone of Sangiovese, due to the prune aroma that characterizes the wine. It has been considered a prestigious wine since the Renaissance, and the number of producers and production area has not expanded much since it was officially delineated. Documents and findings demonstrate that wine production in the area dates as far back as the Etruschi.

Montepulciano’s soil is composed by a mixture of sand and clay, which are perfect for producing well structured, very aromatic wines with fine tannins, however not as mineral as Brunello di Montalcino. Another interesting distinction between Vino Nobile and Brunello is that the latter has cellars scattered all around the municipality, whereas the vast majority of Vino Nobile’s cellars are within Montepulciano’s medieval walls. A great way of depicting the town’s very different histories: one that flourished thanks to farmers turned winemakers and the other from noble families who produced wine and stored it protectively in their palace cellars. Like Brunello di Montalcino, Vino Nobile di Montepulciano is protected under the DOCG appellation, the highest level of recognition that exists.

Sante Lancerio, Pope Paolo the III’s wine expert, would travel all around Italy looking for the best wines to serve the Pope and his court. His note on Vino Nobile was that the wine was “perfectissimo”.

Painting by Italo Zecchi


Fortezza di Montepulciano

Painting by Italo Zecchi

The fortress' existence was first mentioned in the 7th century when it was known as Castrum Politianum and had the purpose of defending the city as its position is extremely strategic: from the top you can see Val di Chiana on one side and Val d’Orcia on the other. The fort which resembles more what we can see nowadays was built in 1261 whilst Montepulciano was under the reign of Siena. A second interesting role the fortress undertook was when, at the end of 1800, Francesco Saverio Melissari bred silkworms in a few of the structure's gigantic rooms. In 1935 it was then transformed into the local high school but has since become Montepulciano’s cultural centre.

Palazzo Contucci interior, image by Palazzo Contucci

Palazzo Contucci

Palazzo Contucci interior, image by Palazzo Contucci

One of the palazzi that sits on the central square is the perfect example of Tuscan architectural Renaissance. Just below the palace are the monumental Cantine Contucci, which were built upon the city’s Medieval walls. The Contucci family is part of the group of families attributable to Vino Nobile’s success—their cellar has been actively producing wine for 1000 years. Their belief on what wine from Montepulciano should be like is the following: “a wine produced from noble grapes intended for the consumption at noble dinner tables”.

Palazzo Ricci's façade, image by wikipedia

Palazzo Ricci

Palazzo Ricci's façade, image by wikipedia

Palazzo Ricci is one of the most well-preserved Renaissance structures in Montepulciano, built in the 16th century on commission by Cardinal Giovanni Maria Ricci, born in 1479 and one of the most influential figures the Vatican had in the sixteenth century. It houses a timeless wine cellar which is known as “the cathedral of wine” as well as a chapel which is ran by the Accademia Musicale Renana. Since 1970 the palazzo has belonged to the town, who has been lending it to the Hochschule für Musik Köln which houses the European Academy of Music Arts since 2001.

Museo Civico di Montepulciano, image by Museo Civico Montepulciano

Palazzo Neri Orselli

Museo Civico di Montepulciano, image by Museo Civico Montepulciano

The palazzo, which used to belong to the Della Robbia family, now houses the Museo Civico di Montepulciano, an archeological museum, worth a visit, especially on a rainy day.

The palazzo is only open Thursdays and Fridays, subject to change according to new regulations.

The cypress-lined road which leads to the Church of San Biagio

Chiesa di San Biagio

The cypress-lined road which leads to the Church of San Biagio

Just below Montepulciano’s historic centre sits the church of San Biagio, often referred to as a temple due to its grandeur. It was built in the 16th century by Antonio de Sangallo the Elder, and is a great example of classic Tuscan Renaissance. Built on a pre-existing pieve which originated in the paleochristian era - around the year 300. Pay close attention to the organ, built by Alamanno Contucci in 1781.

The church is closed to the public on Saturday.

The Duomo, image by E-Borghi

Cattedrale di Santa Maria Assunta

The Duomo, image by E-Borghi

Montepulciano’s Duomo was built between 1594 and 1680, a masterpiece in the hands of the Sienese School, which houses the famous Assumption of the Virgin triptych by Taddeo di Bartolo, who painted it in 1401.

Chisa di Santa Maria delle Grazie, image by Italian Travelers

Chiesa di Santa Maria delle Grazie

Chisa di Santa Maria delle Grazie, image by Italian Travelers

The church is situated behind a beautiful portico with three arches. Inside, pay close attention to the 16th century terracotta altar by Andrea and Giovanni della Robbia.

The well in Montepulciano's main square

Il Pozzo dei Grifi e dei Leoni

The well in Montepulciano's main square

The well found in Montepulciano’s central piazza was designed by Antonio de Sangallo in 1520, when he was residing in the town. The de Medici’s family crest sits above the well: six balls on the front of a shield and Florence’s symbol on the back, with two lions holding up the crest.

Bravio delle Botti, image by Toscana Umbria in Treno


Bravio delle Botti, image by Toscana Umbria in Treno

February - Anteprima del Vino Nobile di Montepulciano
July - Cantiere Internazionale d’Arte
August - Bravio delle Botti - Montepulciano’s historical wine cask competition between all the different contrade.
August - Bruscello - teatro popolare
August - Calici di Stelle
September - Live Rock Festival - over 100 artists perform every year in Acquaviva, a small town just outside of Montepulciano, over the course of 5 days.

Quiet street in Monticchiello

Bike & Walk

Montepulciano to Monticchiello

1 hour 45 minute walk

Begin your walk in Via dei Grassi, Montepulciano, and begin making your way towards Vicolo dei Grassi. Once at San Biagio, walk around the church and turn onto Via di Pescaia. Once you reach the end of the road, keep the farmhouse to your right and turn left, then turn right onto SS146, for a few hundred meters. Keep left onto Via di Poggiano, then keep left at the fork with Via del Termine. After some kilometers you’ll reach an intersection in the woods. Keep left and walk down the winding road. At the intersection keep left again, turning towards Monticchiello, then turn left again on Via 7 Aprile and finally left again onto Via Marino Cappelli, where up ahead of you Monticchiello sits.

Image by


Osteria del Borgo

osteria & view

A family run, rustic osteria with an outdoor terrace overlooking hills, cypresses and medieval forts.

Image by Strada del Vino Nobile

Osteria Porta di Bacco

upscale Tuscan

A great wine selection and refined Tuscan cuisine in Montepulciano’s historical centre.

Image by Histotouring

La Grotta

refined & delicious

Right next to the temple of San Biagio is this delicious restaurant serving classic and reinterpreted Tuscan dishes. Highly recommended for a special occasion.

Image from Pinterest

E Lucevan le Stelle

wine & view

A family owned enoteca with the option of tasting traditional Tuscan dishes or enjoying a drink at sunset.

Image by Enoteca La Dolce Vita

Enoteca la dolce vita

wine & food

The enoteca is home to a great selection of wines, with more than 600 labels, dug into the historic town centre.

Image by @sachabox

Caffè Poliziano

historic cafè & pasticceria

Feel the history etched deep in the walls of this cafè which has been serving locals and tourists their morning coffee since 1868.

Image by La Briciola

La Briciola

rustic Tuscan

Traditional Tuscan food, from crostini with patè to fresh pici with all the trimmings, all accompanied by an excellent selection of local wines.

Image by Il Tosco


Il Tosco

historic palace

A family run hotel with four double rooms in Montepulciano’s historic centre.

Image by Agoda

Locanda San Francesco

historic with a view

A 14th century palace overlooking the Tuscan countryside.

Image by Tablet Hotels

Villa Poggiano

villa & gardens

just 2km from the Medieval town sits a wonderful villa from the 1700’s, entirely restructured and with a marble pool built in the previous century.

Image by Villa Cicolina

Villa Cicolina

noble villa turned modern stay

Entirely renovated 1800’s villa with a great selection of suites and an infinity pool overlooking Val di Chiana.

Image by Lupaia


farmhouse stay

Experience life in an upscale Tuscan podere with the perfect balance between a rustic feel and modern comforts.

Bar in Montepulciano, image by Compass + Twine

Montepulciano's narrow streets


Bar in Montepulciano, image by Compass + Twine

Montepulciano's narrow streets

Bottega del Rame

copper crafts

the last copper craftsmen left in Montepulciano, who sells all sorts of objects and utensils.

Urban Bikery

bike rental

Rent anything from an e-bike to a traditional road bike for your personal excursion or one with an expert local guide



Artisanal goldsmith workshop with a rich selection of unique jewels.

Enrico Crociani


Custom made refined Italian suits and male clothing.



A great selection of handmade jewellery and accessories.