The Val d'Orcia, a UNESCO landscape of cypress roads and wheat fields, is under two hours south of Florence by road. Tours stop in Pienza, Montalcino and Montepulciano.
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Rolling countryside carries this day from Florence, with Pienza, Montalcino and Montepulciano among the stops on several of the listings we describe; the most common length is about 12 hours. We list 19 tours on this page. Reviews of the tours on this page add up to more than 3,106, with an average of 4.6 out of 5. Tours on this page run from 9 to 13 hours.
The listings in this group name Pienza and Montalcino among their stops, and some of them name Brunello and Vino Nobile among their wines. They run from 11 to 12 hours; one itinerary adds Monteriggioni and its medieval walls. One listing in this group is rated 4.6.
Here a meal anchors the day. One itinerary serves a Tuscan lunch of pici and cheeses with wine pairing and runs close to 12.5 hours, while a small-group itinerary of about 10.5 hours dines on three courses in Pienza. The pici listing is rated 4.3 and also lists Italian guiding.
Here the day adds Siena and Cortona, with free time in Siena, Cortona and Montepulciano and a private eight-seater minivan for the road. At about 10 hours it is the shortest day of the three formats we describe. This listing is rated 4.9 and stops at a 14th century cellar.
| Type of tour | ★ | Duration | Includes |
|---|---|---|---|
| Village loop with two tastings | 4.6 | ~12h | Free visit of Montalcino, Pienza and Montepulciano + expert multilingual guide |
| Tuscan lunch with four-wine tasting | 4.3 | ~13h | Guided tasting of 4 wines + free time in Pienza and Montalcino + air-conditioned round trip |
| Siena and Cortona route by minivan | 4.9 | ~10h | English-speaking tour leader + free time in Siena, Cortona and Montepulciano + optional cellar tasting |
The stops differ from tour to tour, so the shape of the day is what to weigh; we would ask first whether you want a set lunch, a tasting circuit or a longer route that adds Siena and Cortona. Among the trips shown here, "From Florence: Val d'Orcia Tour with Wine Tasting" is the most reviewed, with over 1,507 reviews and a score of 4.6 out of 5.
Table data is indicative and comes from the GuruWalk catalogue. Each activity's current details, including availability, are the ones shown on its listing when you book.
A listing can sell the same day with or without extras, so look at which option you pick. "Free time to visit Monteriggioni, Pienza, and Montalcino", one listing notes, and on that listing the wall access in Monteriggioni is not included with the Transfer Only options. We would confirm whether the tasting is part of your choice before paying.
Many of the tours we describe list free time in Pienza, Montalcino or Montepulciano. A day built that way suits travellers who want to wander the lanes of a village; others may prefer a tour that names a leader or guide for the whole trip.
Each tour we describe states free cancellation up to 24 hours before departure. Plans can therefore still change the day before, which is worth knowing when you pick a date.
Pienza and Montalcino come up on most tours we describe, with Montepulciano on several. One adds Monteriggioni and its medieval walls, and another adds Siena and Cortona.
Italian is listed on one tour we describe, alongside English and Spanish. Others list English and Spanish, and some English only.
Two of the tours we describe list a lunch: a Tuscan lunch with wine pairing on one, a three-course lunch in Pienza on the other. For the other days, check each listing for the meal.
