Wine Tasting in Tuscany
- Phil Stewart
- Mar 29
- 5 min read
Updated: Apr 6
As the weather turns warmer this Spring in the UK, thoughts turn to our summer travel plans. Last summer, I did a magical day trip to Tuscany from Rome, with City Wonders, taking in the medieval walled hilltop town of Montepulciano, a three course dinner and wine tasting session at the Pulcino winery and finishing in the afternoon at the UNESCO listed city of Pienza

Unlike the tour to Pompeii from Rome, this tour was much more leisurely, the distances being that much shorter from Rome to Tuscany. Still an early morning start, but the difference here was we arrived at our first stop - Montepulciano by mid morning:



My first impression on seeing the unique hilltop town of Montepulciano was its similarity to the city of Gondor in Return of the King as depicted by Peter Jackson in the 2003 movie of the same name. I have no evidence to suggest J.R.R. Tolkein ever visited Tuscany but perhaps the movie's creator Peter Jackson has? The hilltop location, the walled town and the heraldic flags all looked oddly familiar; but the original is definitely prettier here. Local allegiances mattered in Renaissance Italy, and the people here aligned themselves to city of Florence, which is reflected in the architecture of its town hall - a broader, shorter version of the Palazzo Vecchio in Florence.
Montepulciano was founded in the sixth century by the people of Chiusi who were fleeing a Barbarian invasion. The first settlement was known as Mons Politianus which is why the people are known as Poliziani. Beacause of its strategic hilltop location, the town was constantly fought over between the Sienese and Florentines. In 1202 the people decided upon Florence as its protectorate (hence the eventual town hall replica).

Over the next 200 years Montepulciano changed hands several times before becoming again under the protectorate of Florence in 1511. In modern times, after the unification of Italy, the town became an important centre for agriculture with the drying out of Val di Chiana as an important area for wine production. This region is famous for the Vino Nobile wine. On the last Sunday in August, a.competitive barrel-rolling competition is held where barrels are rolled uphill through the town with participants chosen from each district of Montepulciano and competiting under that heraldic flag.
The tour of Montepulciano was leisurely and relaxed here. There was a tour guide who met us at the town's gate and this continued up to the Torre di Pulcinella with its striking clock tower and Neopolitan character who strikes the bell on the hour. After the guided walking tour, there was then a good amount of time left to explore the town on your own. For me, this meant an excursion to purchase some local pasta:


Before the onwards trip to the winery, there was a photo stop next to the Temple of San Biagio, just at the foot of town:


Arriving at the Pulcino winery just before lunchtime we were given a very warm welcome by the family owners and a short tour of the winery itself. An Italian welcome often involves food and this most certainly was the case here with antipasta, pasta and a dessert wine and biscotti all being served for the tour party:



You will see that the Pulcino winery has very mixed reviews on Tripadvisor so I wanted to provide my own take on this. I found the food and wine tasting to be excellent and had no cause for complaint on either front. However, I do agree with the reviews that the experience in the shop was very disappointing for a number of reasons. Firstly the items were not marked with a price. Secondly, at the till I was asked for cash rather than a card payment (they do accept card payments to clarify). Whilst I appreciate that Italian merchants pay slightly larger merchant card transaction fees than the rest of the European Union average, this is the same for all Italian merchants, who do not engage in this behaviour. I also found that the wine I purchased in the shop was significantly cheaper back in the UK by a considerable margin (£50 in the shop vs. £25 at home in the UK) and the currency conversion alone did not account for the difference in price. My only conclusion then is that there must be considerable mark-up going on in store so I would not purchase again from this store. It left a sour taste in my mouth, if you'll excuse the culinary pun. It's a shame because it's tainted in hindsight what was up to that point a wonderful experience.
The day was rounded off with a visit to the UNESCO listed town of Pienza. Owned in part by the Piccolomini family since 1300, it then became home to the exiled Silvius Piccolomini who became Pope Pius II. He had the town rebuilt by the Florentine architect Bernardo Rossellino from 1459 onwards. It became the blueprint for municipal centres across Italy due to its humanist urban planning concepts.

The town is very compact and is easily walkable. Perhaps one of the more famous attractions is the Palazzo Piccolomini since it was used as a location for the 1968 movie of Romeo & Juliet by Franco Zeffirilli:



The Palazzo and its gardens (with its stunning views of the Val d'Orcia) are accesible for a small fee. Outside the main entrance to the palazzo is a wonderful ice cream parlour serving the most amazing Italian ice cream.


In closing, I highly recommend this enchanting day tour from CityWonders as overall it represents excellent value for money (two town visits and a tour of Montepulciano , wine tasting and a three course lunch). I caveat the recommendation with I cannot recommend purchases from the Pulcino winery shop at the tour end, owing to their not price marking items and insisting upon cash payments. In my experience, stores not marking prices are either high end luxury or are trying to conceal something. I will leave the reader to deduce which applies here.

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