Booking choice: The Tuscany in One Day tour, from $115 per person. Check dates Compare the options below
The two towns sit about 15 minutes apart on the ridges above the Val d'Orcia. Montepulciano is the bigger, steeper wine town; Pienza is small, calm and almost perfectly Renaissance.
On the classic tour you have a guided walk in Montepulciano and free time in Pienza, so it pays to know what you want to see.
The quick answer
In Montepulciano, walk up to Piazza Grande for the cathedral and town hall, and look into a Vino Nobile cellar. In Pienza, see Piazza Pio II, the cathedral and Palazzo Piccolomini, then walk the lanes to the terraces over the valley and buy pecorino. The classic day gives you a guided walk in the first and about an hour in the second.
Where are Montepulciano and Pienza?
In the Val d'Orcia area of southern Tuscany, in the province of Siena, about 160 to 170 km north of Rome.
The Val d'Orcia has been a UNESCO World Heritage cultural landscape since 2004. Pienza sits above the valley itself; Montepulciano is on the next ridge to the east, looking over vineyards.
What should you see in Montepulciano?
Piazza Grande at the top of the town, with the cathedral of Santa Maria Assunta and the town hall, and one of the wine cellars under the streets.
The main street climbs steeply from the lower gate to the piazza, lined with palaces, shops and cellar doors. Film fans may recognise the square from The Twilight Saga: New Moon. Below the walls stands the Renaissance church of San Biagio, begun in 1518, which the classic tour visits as a photo stop.
See it with a local guide: the classic day includes a guided walk in Montepulciano.
Check dates for the Tuscany in One Day tourWhat is Vino Nobile di Montepulciano?
The town's red wine, made mainly from Sangiovese (locally called Prugnolo Gentile), and one of Italy's first DOCG wines.
Many cellars in the old town offer tastings, some in tunnels dug into the hill. On the tours, the wine comes with lunch; for more tasting time, see Tuscany wine tours from Rome.
What makes Pienza special?
It is a Renaissance planned town: Pope Pius II, born there in 1405, had his home village rebuilt as an ideal city from around 1459.
The architect Bernardo Rossellino laid out Piazza Pio II with the cathedral, Palazzo Piccolomini and the town hall around it, and the historic centre has been a UNESCO World Heritage Site since 1996. It is small: you can walk end to end in ten minutes.
What should you do with free time in Pienza?
Walk to the terraces on the southern edge for the view, wander the tiny lanes, and taste pecorino.
The lanes have names like Via dell'Amore and Via del Bacio (the street of love and the street of the kiss). The cheese shops along the main street sell the local pecorino, young and aged, often vacuum-packed to travel.
Montepulciano with a guide, a farm lunch and free time in Pienza, from Rome.
Explore the Tuscany in One Day tourHow much time do the tours give you?
Around two hours in Montepulciano with the guided walk, and about an hour of free time in Pienza, depending on the day.
The Tour Guy's day also gives an hour in Pienza, after Civita and a winery. Veditalia swaps Pienza for Montalcino. A private driver lets you set your own times.
| Tour | Montepulciano | Pienza | Also |
|---|---|---|---|
| City Wonders | Guided walk + San Biagio | Free time | Farm lunch |
| The Tour Guy | Winery nearby | 1 hour | Civita di Bagnoregio |
| Veditalia | Winery + tasting | No | Montalcino |
| Private driver | Your pace | Your pace | Lunch extra |
Is it easy to walk?
Montepulciano is steep and cobbled; Pienza is flat and easy.
Wear shoes with grip, and take the walk up Montepulciano's main street slowly in summer. The tours are not wheelchair accessible.
Can you add Montalcino or Bagno Vignoni?
Montalcino is on the small-group and private options of the classic tour and on the Veditalia day; Bagno Vignoni needs a private car.
Bagno Vignoni, whose main square is a thermal pool, is a short drive from Pienza and a good reason to book a private driver.
Want Montalcino too? The Veditalia day covers Montepulciano and Montalcino.
Check dates for the Montepulciano and Montalcino dayFrequently asked questions
Which is better, Montepulciano or Pienza?
They are different: Montepulciano for wine cellars and a grand hilltop square, Pienza for Renaissance calm, views and pecorino. The classic day gives you both.
How far is Montepulciano from Pienza?
About 13 km, roughly 15 to 20 minutes by road.
Was Twilight filmed in Montepulciano?
Yes, scenes of The Twilight Saga: New Moon were filmed in Montepulciano's Piazza Grande.
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Choose your day
Free cancellation up to 24 hours before on every option. Prices are from-prices in USD and move with the season.
Tuscany in One Day: Val d'Orcia, Wine & Lunch
- Round-trip air-conditioned coach from Rome with Wi-Fi
- Guided walk in Montepulciano with a local guide, photo stop at San Biagio
- Three-course lunch at a Tuscan farm and winery, wine tasting incl. Brunello
Montepulciano & Montalcino Wine Day
- Round-trip air-conditioned coach from Piazza del Popolo, 7:30
- Medieval winery with a 2,000-year-old Etruscan tomb
- Vino Nobile and Rosso di Montalcino tasting with a sommelier
Montepulciano & Pienza Private Day
Your own driver and hotel pickup; lunch and guide extra
