Day Trips from Siena to Pienza

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Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Please note that from November to April, and in case of bad weather, lunch will take place indoors. For tours departing on Mondays, lunch is always served in an indoor restaurant. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

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Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.6

(5)

from $269

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

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Private Montalcino and Pienza Tour from Siena

6 hoursFree Cancellation

4.0

(3)

from $549

Price varies by group size

Discover Tuscany's stunning landscape, culinary delights, and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Avoid the hassle of driving yourself and be led by a local guide. Admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with a visit to a winery.

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Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

4.9

(319)

from $223

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

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Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

8 hoursFree Cancellation

5.0

(38)

from $823

Per group

Private Taste of Tuscany Tour

9 hoursFree Cancellation

5.0

(1)

from $388

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Follow the rolling cypress-lined roads south from Siena to reach Pienza, the Renaissance city built by Pope Pius II. Book a day trip to tour the sights, admire the architectural harmony of the Piazza Pio II, and sample the famous Pecorino cheese from local shops. Spend the afternoon walking the scenic city walls for a bird’s-eye view of the Val d’Orcia or tasting local honeys. Guided tours simplify the regional travel through the winding Tuscan hills, returning you to Siena without the stress of navigating the country roads.

Day Trips from Siena to Pienza

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