Pienza Tours and Tickets - page 3

49 results

Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up

Escape the bustling streets of Rome and explore the picturesque Val d’Orcia on this private day trip. With a friendly English-speaking driver, visit the charming towns of Montepulciano, Pienza, and Montalcino, known for their stunning landscapes and rich wines. Enjoy the flexibility to customize your itinerary to include a winery visit and tasting, or simply savor the breathtaking views and local cuisine at your own pace. This tour offers a unique glimpse into Tuscan culture, perfect for wine enthusiasts and travellers seeking a personalized experience. - Private transportation in a comfortable Mercedes sedan or minivan - Explore UNESCO-listed Val d’Orcia, stopping in Montepulciano and Montalcino - Customize your itinerary with optional winery visits and lunch - Full-day tour lasting approximately 10 to 11 hours from Rome, with hotel pick-up and drop-off

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Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up

9 to 10 hoursFree Cancellation

from $1,125

Price varies by group size

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What are people saying about Pienza

Small-Group Montepulciano and Pienza Day Trip from Siena

Catherine_D, Jun 2026

Tutto benissimo

10/10 would recommend. Keko was a knowledgeable and charismatic tour guide. While we drove through the Tuscan countryside, he provided engaging commentary about the history, the landscape, and the local food traditions of the region. If you want to see the Tuscan country, this is the way to do it. I particularly enjoyed the lunch at the farm and tasting the local recipes with ingredients made right there. The time in Pienza and Montepulciano flew by. I would definitely take this tour again.

Private Guided Tour of Pienza on Foot

Mark_C, May 2026

Great

Guide extremely knowledgeable. Really enjoyed conversation and meeting locals. Duration of tour was good. Provided great perspective of Pienza.

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Madeleine_R, Apr 2026

So much fun! The farm was...

So much fun! The farm was a definite highlight -- gorgeous views and incredible snacks to kickstart the day! We loved getting to walk around Pienza, and the wine was incredible (though definitely pricey if you wanted to purchase bottles to ship home). All in all a perfect way to explore Tuscany. We also loved our guide Frederico! The perfect balance of informational and letting us relax without pressure.

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Kevin_L, Feb 2026

The Perfect Tuscan experience!

Exactly what we were looking for! A unique experience-. Mattea was a colorful guide, fun and knowledgeable of the area and wines. A small self sustaining cheese farm with olive oil and wine. Pienza is a must see and finally a private wine tasting in montalcino.! Thanks Mattea for a great day!

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Cynthia_P, May 2026

Great scenery and wine

Beautiful scenery and lovely wine. Second time taking this tour. The quality of the lunch has decreased since last year but the scenery is still wonderful from restaurant terrace. Wine pours seemed to be smaller and wine prices are up. Driver was diligent but parking was a challenge and we needed to walk further than last year to reach the restaurant in Pienza and the winery in Montepulciano. This was a bit of a challenge for me in 90+ F degree heat.

Small-Group Montepulciano and Pienza Day Trip from Siena

Jennifer_H, Jun 2026

Our time in Montepulciano...

Our time in Montepulciano was one of our favorite days in Italy. Giovanni was an exceptional guide and he taught us so much about the wine and the area. We highly recommend Tuscan Wine Tours as they book small wineries. Our delicious lunch was at a dairy farm where we overlooked the gorgeous Tuscan region.

Pienza

5.0

(1,082)

Tuscany

Know before you go

Aerial view of the medieval village of Pienza near Siena, Italy.

Wear comfortable walking shoes; the town is best explored on foot.
Some tours of Pienza may include entrance fees, transportation, guides, food, and drink; check with your tour company for details.xa0
Pienza, while small, makes a great home base for exploring the area, and there are a number of hotels in town.

Things to do near Tuscany

More attractions near Tuscany

Things to do in San Gimignano Things to do in Florence Things to do in Chianti Things to do in Montecatini Terme Things to do in Siena Things to do in Lucca Things to do in Pisa Things to do in Livorno Things to do in Arezzo Things to do in Montepulciano Things to do in Isola d'Elba Things to do in Maranello Things to do in Bologna Things to do in La Spezia Things to do in Versilia